Samplebook-Tools of Organic Chemistry
Samplebook-Tools of Organic Chemistry
Samplebook-Tools of Organic Chemistry
Organic
Chemistry
For world of competitions
By
(i)
(ii)
Preface
The guiding principle in writing this book was to create
a textbook for students- a textbook that presents the
ma terial in a way tha t they le arn to solve all the
questions along with the strategy to approach the
problems.
In this book we mixed all our teaching experience of 11
yea rs a long with theora tica l a nd experimenta l
knowledge to generate a hand book for all students to
reason their way to a solution rather than memorize a
multitude of facts, hoping they dont run out of memory.
This book covers mainly 4 units with 61 sections which
are real tools of Organic chemistry, which a students
must know before dealing any chemical reactions.
Organic chemistry is very easy and conceptual subject
and need proper understa nding of the basics a nd
stretegy to solve the questions in corret manner.
This book will prepare your right mindset for learning
Organic Chemistry. This mindset is essentially the one
that focuses you on a small number of straight forward,
repeated, funda menta l concepts a nd helps you to
apply them in different ways to solve the variety of
problems you face in organic chemistry.
This book is complete as it not only covers theory in
proper sequence but also provide varieties of questions
along with 10 test papers to judge your knowledge before going to start chemical reactions.
This book a lso covers a ll the questions of AIEEE,
IIT-Mains, IIT-Advanced, AIPMT & other medical exams from 2000 to 2014.
In this book balance has to be achieved between the
number of questions and the quality of the questions,
(iii)
www.
co.in
(iv)
(v)
Acknowledgement
We are tha nkful to all the teachers who taught us
during the concept building session of our life specially
Dr. Nizamuddin sir, senior Chandra Vijay Rao and Dr.
Vijay Pratima Mittal madam.
We have written this book to remove the fever of
organic chemistry from mind of students.
We particularly want to thank many wonderful and
talented students whom we have taught over the years
who in turn taught us how to be a good teacher and
how we can help others.
We want to make this book as user friendly as possible,
and we will appreciate any comments that will help us
to achieve this goal in future editions.
Finally, this edition has been presented before you with
efforts to make it error free. Any that remain are our
responsibility; if you find any, please let us know so they
can be corrected in future printing.
Ajnish Gupta & Bharti Gupta
Professors of Organic Chemistry
[email protected]
09122057123
(vi)
Table of Contents
Page No.
Unit 1 : Basic understanding of organic chemistry
01
02
06
09
15
18
25
29
34
Section 09 : Hybridization
38
42
47
51
Answer
63
: Subjective approach
Answer
79
79
90
95
97
98
99
: Objective approach
(vii)
100
101
102
106
111
116
122
131
135
157
163
168
Answer
194
: Subjective approach
214
214
228
233
234
238
Answer
: Objective approach
Test 1
Test 2
241
Test 3
240
(viii)
250
259
268
269
270
273
277
281
Section 05 : Metamerism
285
292
298
303
310
315
326
331
336
344
351
354
360
(ix)
366
Answer
: Subjective approach
384
401
401
434
441
442
445
Answer
: Objective approach
446
Test 4
: Concept of isomerism
449
Test 5
: Concept of isomerism
459
Test 6
: Concept of isomerism
468
Test- 4, 5, 6 : Answer
478
479
480
487
491
495
499
504
Section 07 : Hyperconjugation
508
511
514
Section 10 : Carbocations
517
520
524
532
Section 14 : Carbanions
535
(x)
540
Section 16 : Carbenes
546
Section 17 : Nitrene
550
Section 18 : Benzyne
554
558
567
572
577
581
Answer
607
: Subjective approach
639
639
697
709
712
723
Answer
: Objective approach
726
Test 7
729
Test 8
739
Test 9
749
Test- 7, 8, 9 : Answer
759
Test 10
760
Test 10
: Answer
769
(xi)
Dedication
Dedicated to all those students who
are in fever of organic chemistry.
(xii)
Unit
Basic understanding of
Organic Chemistry
This section is designed to lay the foundation for your organic
chemistry. Here you will learn what is organic chemistry, how
orga nic compounds are represented, what is the reason for
formation of large number of orga nic compounds, functional
groups, homologues, nature of carbon & hydrogen, saturation and
unsaturation, hybridization, cla ssification of organic compounds
and Baeyers strain theory.
Section
Introduction of
Organic Chemistry
Have you ever thought that when you read anything from any
book your eyes use an organic compound (retinal) to convert visible
light into nerve impulses. When you pick up this book from any
place, your muscles do chemical reactions on sugars to give you
energy. As you read the words a nd sentences of this book, gaps
between your brain cells are being bridged by simple orga nic
molecules (neurotransmitter amines) so that nerve impulse can be
passed around your brain and you can understand a ll matters
correctly a nd you did all that without consciously thinking about
it.
You do not yet understand the se processes in your mind but
you are regularly carrying them out in your brain & body.
H 3 C CH 3 CH 3
HO
CH 3H 3 C
O
11-Cis retinal H
(Absorbs light when we see)
You are not alone there.........
NH2
N
H
Serotonin
(Human neurotransmitter)
Are you now thinking for drugs - Then they are again
organic and ma de up of carbon such as coca ine, nicotine,
etc.
MeOOC
N
O
H3 C
CH 3
CH 3
Damascenone-The smell of rose
Cocaine O
HO
HO
CH 3
Cis Jasmone of jasmine
HO
OH
Vitamin C
OH
O
HO
HO
OH
OH
Glucose
CH 3
H3 C CH 3
CH 3
CH3
COOH
Aspirin
CH3
CH 3
OH
Vitamin A
NH 2
N
HN N
Adenine
O
N
NH
NH
HN N NH 2
Guanine
NH 2
N
N O
H
Cytocine
HN
O
Indigo dye for blue colour
O
NH
N O
H
Uracil
H3 C
NH
N O
H
Thymine
Section
soap
H 3O
Fatty acid
In 1828, vital force theory again got a heavy blow when Friedrich
Whler prepared organic compound urea, of human urine from
inorganic compound ammonium cyanate.
Heat
NH 4 OCN
NH 2CONH 2
Ammonium Cyanate
Urea
number of electrons
number of protons
12
Symbol
Atomic mass
Section
Representation of Organic
Compounds
Organic chemistry is the study of compounds that contain
carbon but there are some other elements too associated with it such
as H, O, a nd N. We know that carbon is tetravalent in nature and
form covalent compounds by sharing of electrons by generally H,
F, Cl, Br, I, N, O, S and P. For sake of simplicity all halogens are
generally represented by X. In the study of molecules, you will notice
that oxygen has two covalent bonds, nitrogen has three covalent
bonds and carbon has four covalent bonds when they a re neutral.
Neutral hydrogen & halogens each have one covalent bond. If atoms
have more bonds or fewer bonds than the number required for
neutral molecule then they would have either a formal charge or an
unpaired electron. These numbers are very much important to
remember when you are first dra wing structures of organic
compounds because they provide a quick way to recognize when
you have made a mistake.
C
Cl
Br
s-s overlap
s-p overlap
yx
yx
z+
z
p orbital p orbital
yy
+
Py
Py
10
....
H
HCH
H
2.
.... .
H
HCO H
H
H
H
H
C=C
HC
CH
3.
4.
11
Pentane
Cyclohexane
Benzene
OH
O
end C have 3 H these C atoms must also carry
atoms
1 H atom because only 3 bonds all 4 bonds are shown to
are shown for each atom
this c atom so no H
atoms are implied
12
CH 3
H
A.
Wedge-dash projection or perspective formula:In this wedge-dash projection, the solid wedge (
) is
used to indicate a bond projecting above the plane of paper,
towards the observer and dashed wedge (
) is used to
depict the bond projecting below the plane of the paper
and away from the observer. The bonds lying in the plane
of the paper are depicted by using a normal line (
).
bonds are in
the plane of paper
(Normal line)
H
H
H
bonds are towards the observer
(Solid wedge)
NH 2
or
CH 3
COOH
13
B.
NH 2
or
COOH
CH 3
H is assumed to be above the plane
Fischer projection:
In this projection molecule is represented by horizontal and
vertical lines. Groups on horizontal line are above the plane
(towards the observer) and groups on vertical line are
behind the plane (a way from observer) a nd point of
intersection of horizontal and vertical line is carbon.
H
H
C H
H 109.5
Perspective formula of methane
14
Section
Li
Be
15
16
Li Be
Carbon
At. mass = 12.01 At. radius = 67 pm
Valency = 4
E. Con. = [He]2s2p2
EN = 2.5
Structure = Hexagonal
Na Mg 3
18
13 14 15 16 17 He
B
9 10 11 12 Al Si
N O
F Ne
Cl Ar
K Ca Sc Ti V
Rb Sr
Cs Ba
Fr Ra
Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
Rf Db Sg Bh Hs Mt Ds Rg
La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
17
Section
Functional Groups
A functional group is an atom such as halogen (-X) or group of
atoms such as carboxylic acid (-COOH) in a molecule that gives the
molecule its characteristic chemical properties. They are the action
group or reactive site in a chemical reaction and the remaining
hydrocarbon part remains inert.Each functional group undergoes
characteristic chemical reaction so by recognizing them it is possible
to predict the reaction, which that molecule undergoes.
O
HO
CH3
Carboxylic acid
CH 3
Inert
hydrocarbon part
18
A molecule may have more than one functiona l group and are
ca lled as poly functiona l group compounds or simply poly
functional compounds and properties of each functional group may
be modified by the presence of other.
O
O
Ketone
HO
OH
Alcohol
Carboxylic acid
(Polyfunctional compound)
As carbon has 4 valencies therefore compounds with all single
bond, one double bond or with one triple bond may be formed with
any atoms, which satisfy octet rule.
Functional group with bond onlyCarbon may combine with those atoms which needs 1
electron for completing their octet (such as hydrogen or
halogen) or with some groups which require one electron
for completing octet such as alkyl group (CH3 , CH2 CH3,
etc.), hydroxyl group (OH), alkoxy group (OCH 3 ,
OCH2 CH3 ), amino group ( NH2 ), thiol group ( SH) or
thioether (SCH3) to form corresponding functional groups.
|
C H/C Alkane
|
C OH Alcohol
|
C X Alkyl halide
|
|
C SH Thiol
|
19
C S C Thioether
C N H 1 amine
C N C 2 amine
C N C 3 amine
|
H/C C H Aldehyde
O
O
Carboxylic
Acid
H/C C OH acid
H/C C O C H/C anhydride
H/C C N H 1 amide
H/C C N C 2 amide
H/C C N C 3 amide
|
C C C Ketone
C
Along C=N bond
C/H
C/H
C=NH Imine
C/H
C=NR
C/H
R/H
R/H
C=NOH Oxime
R/H
20
Alkyl imine
(Schiff base)
R/H
C=NNH 2 Hydrazone
C/H
C=NN
C/H
H NO
2
C/H
C/H
NO 2 2,4-Dimitrophenyl hydrazone
C=NNCNH 2 Semicarbazone
H
C=C
Alkene
Ph
C=PPh Methylene triphenylphosphene
Ph
H/C Alkynes
C Isonitriles (Isocyanide)
21
2-
Cl
Cl
Re
Re
Cl
Cl Cl
Cl
R
O
O
Carbonate ester
R
O
Carboxylate
R
Benzene
R
O
H
Hydroperoxy
O
R
S
O
O
R
Peroxy
R
H
Carbonothionyl
N
H
Imide
HO
OR
R
R
Hemiketal
22
HO
OR
R
H
Hemiacetal
RO
OR
R
R
Ketal
RO
OR
R
H
Acetal
RO
OR
R
OR
Orthoester
OR
RO
OR
Orthocarbonate ester
RN
R
3 Amine
RN
RN
H
1 Amine
H
2 Amine
R
RN
R
R
4 Ammonium salt
HN=N+ =N
Azide
R O
N
Cyanate
RN=C=O
Isocyanate
N=N
R
Azo
O
ON+
R
O
Nitrate
R N C
Isonitrile
RN
O
Nitro
S
R
S
Disulfide
O
RSR
Sulfino
O
O
Nitroso oxy
N
R
O
Nitroso
RSOH
O
Sulphonic acid
RSR
R
R
Sulfinile
O
Sulfonyl
R S
N
Thiocyanate
23
OH
H3 C
H3 C
CH 3
Alcohol
Phenol
H3 C
N OH
H3 C
Oxime
H 3C
OH
Carboxylic acid
H3 C
Cl
H2 C
Vinyl halide
H3 C
CH 3
Alkyl halide
Cl
H2 C
Cl
Allyl halide
O
H3 C
H3 C
Cl
Acid halide
O
O
Ether
CH 3
H3 C
NH 2
CH 3 R
Amine
Acid anhydride
H3 C
Aryl halide
O
Ester
CH 3
NH 2
NH 2 R
R
R
Amide
Hydrazone
24
Section
Example: 2
O
(a) CH COH
3
Homologous sereis
of alkanes
(b)
CH 3 CH 2 COH
25
(c)
CH 3 CH 2 CH2 COH
(d)
CH 3 CH 2 COCH 3
Here (a), (b), (c) are homologues but (d) is not homologue of (a),
(b), (c) as it has different functional group.
Insert CH 2 unit
O
H
CH2
H 3C
Homologues
Insert CH 2 unit
O
H
H 3C
O
Carboxylic acid
O
H 3C
CH 3
O
Ester
Not Homologues
O
Cu/Heat
CH 3
CH 3
OH
KMnO 4 /Heat
OH
General formula
Example
series
Alkane
CnH2n+2 (n=1)
CH4 , n=1
Alkene
CnH2n (n=2)
C2 H4 , n=2
Alkyne
Alcohol
CnH2n-2 (n=2)
CnH2n+1 OH (n=1)
C2 H2, n=2
CH3 OH, n=1
Carboxylic acid
Carbohydrate
C6 H12 O6 n=6
28
Section
29
H3 C
CH 3
3
1 CH
CH 3
3
H3 C
CH 3
H3 C
H3 C
CH 3
CH3
2 1
CH 3 CH 3
1
CH3
H3 C N 2
CH3 O
CH 3
1H=15
2H=5
3H=0
30
CH 3
1
O
H3 C
Cl 2
3
1
2
Cl
S Br
1H=5
2H=8
3H=0
2
H3 C
H
N
NH
1
HS 2 NO 2
1H=4
2H=2
3H=0
H
+OH
H3 CCH 3
Alkane
H
+NH 2
H3 CCH 3
Alkane
H
+SH
H3 CCH 3
Alkane
H
+NO 2
H3 CCH 3
Alkane
H
+SO 3H
H 3C
Alcohol
NH 2
H 3C
Primary amine
SH
H3 C
Thioalcohol
NO 2
H 3C
Nitro alkane
SO 3 H
H 3C
Alkane sulphonic acid
Cl
H3 C
Cl
1 Alkyl halide
H3 C
CH 3
2 Alkyl halide
H3 C
CH 3
3 Alkyl halide
31
H3 C
OH
1 Alcohol
CH 3
OH
CH 3
H3 C
2 Alcohol
CH 3
CH 3
OH
2 Alcohol
OH
OH
1 Alcohol
H3 C
CH 3
3 Alcohol
3 Alcohol
CH 3
O
H+H
O
H 2 O
Alcohol
O
Ether
CH3
H 3C
O
H+H
Carboxylic acid
H 2 O
Carboxylic acid
CH 3
H3 C
O
H+H
Carboxylic acid
H 2 O
H3 C
CH 3
CH3
H 3C
H+H
Carboxylic acid
O
Ester
Alcohol
O
O
H3 C
O
CH 3
Acid anhydride
32
CH 3
H 3C
NH
H 2 O
Primary amine
H3 C
NH
CH 3
Primary amide
H 3C
NH 2 + H NH
NH 3
Primary amine
Primary amine
CH 3
H3 C
NH 2 + H
Primary amine
CH 3
H 3C
NH
Secondary amine
CH 3
H 3C
N
NH 3
CH 3
Secondary amine
H 3C
Tertiary amine
H3 C
1 Amine
CH 3
2 Amine
3 Amine
NH
NH
2 Amine
2 Amine
CH 3
3 Amine
CH 3
NH 2
H3 C
CH 3
1 Amine
NH
2 Amine
N
3 Amine
3 Amine
33
Section
34
A B C D
A B
Substitution reaction
Addition reaction
C D
H3 C
CH 3
O
H3 C
OH
H3 C
CH 3
H3 C
CH 3
S
NH 2
H3 C
CH 3
CH 3
SH
CH 3
H3 C
CH 3
OH
O
NH
N
H
H3 C
CH 2
H3 C
H3 C
O
H3 C
CH
CH 3
H3 C
O
OH
H3 C
NH 2
O
H3 C
NH
OMe
OH
O
N
35
CH 3 CH 2CH2 Cl
Derivative of alkane
Derivative of alkene
H3 C
H3 C
NO 2
36
Cl
CH 3
H3 C
H3 C
OH
CH 3
H3 C
H3 C
SO 3 H
NH 2
CH 3
O
CH 3
H3 C
CH 3
N
+
N
H3 C
CH 3
CH 3
CH 3
+
S
CH 3
CH 3
H3 C
H3 C
0 H
0 OH
H3 C
H3 C
0 Cl
H3 C
CH 3
0 COOCOCH3
CH 3
0 COOCH 3
0
CH 3
O
O
0
OH
Base
Aldehyde
having H
CH3 CHCH2 CH
0
-Hydroxy
aldehyde
CH 3 CH=CHCH
0
,-unsaturated
aldehyde
37
Section
Hybridization
When we carefully look over the organic molecules we will find
that some carbon atom is single bonded while some others are
multiple bonded. These single or multiple bonds create some fixed
shape or geometry in molecule such as linear, planner, tetrahedral,
etc. Molecular geometry or molecular structure is the 3-dimensional
arrangement of the atoms that constitute a molecule. It determines
several properties of a substance including its reactivity, polarity,
phase of ma tter, color, magnetic properties, and even biological
activities. The molecular geometry can be determined by various
spectroscopic methods & diffraction methods such as Infrared (IR),
microwave & Raman spectroscopy can give information about the
molecule geometry. X-ray crystallography, Neutron diffraction and
Electron diffraction can give molecular structure for crystalline
solids based on the distance between nuclei and concentration of
electron density. Gas electron diffraction can be used for small
molecules in the ga s phase. Nuclear magnetic resonance (NMR)
& Frste r (Fluorescence) resona nce ene rgy tra nsfer (FRET)
methods ca n be used to determine complementary information
including rela tive dista nces, dihedra l a ngles, a ngles, a nd
connectivity. Molecular geometries a re best determined a t low
38
120
109.5
Tetrahedral shape
Planner shape
A
Linear shape
39
(G) Seesaw
(H) T shaped
(I)
(J)
Octahedral
Square pyramidal
sp3
sp
H3 C OH
H2 C
sp 2
sp2
sp
sp2
H2 C C CH 2
O
sp3
sp 3
sp3
3
sp2
sp
CH 3
sp2
sp2
sp
sp
sp 2
H2 C
sp3
sp2 sp
sp2
CH 2
CH
sp
sp2
sp2
sp2
sp
sp 2
sp2
40
..
NH
H2 C
sp 2
.SH
. sp
..
H2 C
.OH
. sp
..
sp 2
CH
H2 C
.O.
sp 2
H2 C
..NH
sp 2
or
Cyclooctatetraene = COT
or
10 Annulene
(Non Planner)
41
Section
10
Classification of organic compounds
Up to this point you are familiar with the common functional
groups, sa tura ted a nd unsa turated compounds with their
hybridiza tion and shape so now we can cla ssify the organic
compounds into different categories on the basis of their shape and
stability. Organic compounds are divided into two classes- Acyclic
or aliphatic & cyclic compound. Acyclic compounds or aliphatic
compounds a re those which do not have any ring. The word
aliphatic comes from aleiphar which mean fat or oil. Here carbon
atoms can be joined together in straight chains or branched chains.
They can be saturated, joined by single bonds (a lka nes), or
unsaturated, with double bonds (alkenes) or triple bonds (alkynes).
Besides hydrogen, other elements can be bound to the carbon chain,
the most common being oxygen, nitrogen, sulfur and halogen. The
simplest aliphatic compound is metha ne (CH4 ). If a liphatic
compounds are cyclic in nature then such compounds are called
as alicyclic (Aliphatic + cyclic) such as cycloalkanes, cycloalkenes,
cycloalkynes, cyclic esters, cyclic ketones etc.
42
HO
NC
CN
HO
NC
H3 C
Ph
CN
CH 3
Ph
+
+
Ph
Ph
O
Ph
Ph
O
+
+
43
H 3C
+
N
Fe
Ferrocene
+
CH 2
Tropylium ion
Group
+
CH 2
Substituted
Benzene
H
N
Pyrole
Furan
Thiphene
N
Imidazole
N
Pyridine
CH 3
N N
O
Pyrylium ion
Nicotine
NH 2
NH 2
COOH
N
N
Pyrimidine
44
N
Niacin
N
O
N
N
H
HO
Cytosine
OH
HN
N
N
H
HO
OH
CH 3
N
H
CH 3
HO
Thymine
Uracil
N
Quinoline
Naphthalene
NH
S
Benzothiophene
Benzofuran
Indole
N
Indenyl anion
NH
N
N
Purine
N
N
NH
H2 N
NH
N
Adenine
N
N
N
NH 2
Azulene
Indole
NH
NH
H 2N
N
OH
NH
N
Guanine
Anthracene
Phenanthrene
Phenalenyl anion
45
(14) Annulene
Cycloprop-2-enide ion
Cyclobuta-1, 3-diene
+
Cyclopenta-2,4-dienylium ion
46
Section
11
10928'
2444'
60
2444'
47
No. of C
Angle between
Distortion
in the ring
or strain
Cyclopropane
600
24 0 44
Cyclobutane
900
9 044
Cyclopentane
1080
0 044
Cyclohexane
1200
-5 0 16
Cycloheptane
1280 34
-9 0 33
Cyclooctane
1350
-12 0 62
48
H
C
H C
H
C H
H
Heat of combustion
Total
atom in ring
KJ/CH 2
strain in KJ
697
120
685
112
664
35
659
12
662
35
8-11
661-665
32-88
12-onwards
657-661
0-48
49
Chair
Half chair
Twist boat
Boat
50
Exercise
01
Subjective Approach
You cant mug-up organic chemistry because theres too
much of it. You can remember trivial things like name of compounds
but that doesnt help you to understand the principle behind the
subject. You have to understand the principle because the only
way to tackle organic chemistry is to learn to work it out. That is
why we are first providing you some questions so tha t your
understanding about the topic should be increased. These problems
will set you on your way but they are not the end of the journey, as
here you a re beginning your journey to understa nd organic
chemistry.
The problem would be of little use to you when you could
not check your answers. For the maximum benefit, you need to solve
all the problems without looking the answers. Then you should
compare your answers or suggestions with ours before going to
next chapter. If any answer is mismatch then darken those question
numbers with red pen and again have a microscopic look over it
and its theory and correct it before proceeding further. Here starts
the first set of 60 questions
01. What is organic chemistry? Write at least 4 characters which
distinguish organic compounds from inorga nic compounds.
51
NH
H
H H
N
OH
H3 C
H
NH 2
14. What is the carbon carbon bond length in ethane, ethene, ethyne
& benzene?
15. Which bond is weaker in C-H & C-C bond of alkane?
16. Write the decreasing order of bond strength of carbon- carbon
single, double a nd triple bond?
17. How many electrons are involved in formation of single, double
and triple bond?
52
53
O
H3 C
CH 3
H3 C
H3 C
CH 3
Cl
O
H3 C
H3 C
CH 3
(B) CH5 N
(D) C2 H4 O (3 possibilities)
54
(C) C2 H6 O (2 possibilities)
(E) C3 H9 N (4 possibilities)
SH O
CH 3
SH
Compound with worst smell
I
H 3C
CH 3
CH 3
Compound with worst smell
II
O
O
Olean sex pheromone of olive fly
(III)
N
CH 3
N CH 3
Compound from coffee
(V)
O
Compound from cakes & biscuits
(VI)
O
OH
H 3C
H 2C
Cl
Vinyl chloride
(IV)
O
Corylone
ceramel roasted protein
(VII)
OH H
N
CH 3
CH 3
Zeneca's tenormin
For treatment & prevention
of heart deasese
(VIII)
55
OH
CHO
HO
Vanillin of vanilla
(IX)
N
Pyridine
(X)
N +2 Cl
Aniline
(XII)
H 3 C CH3
OOH
H H
N
O
Phenol.
(XI)
H3 C CH 3
CH 2
NH 2
CH 3
CH 3
COOH
O
Penicilin
(XVII)
CH 3
Nicotine
(XVIII)
CH 3
COOH
Aspirin
(XIX)
EtO
H
N
HO
CH 3
O
Paracetamole
(XX)
H3 C
S
N
NH
N
N
O
O
H 3C
CH 3OH
CH 3 H
H
H
O
Testosteron (Hormone)
(XXII)
56
O
H3 C N
O
O
Cocaine O
(XXIII)
CH3
H2 C
OH N
O
HO
H 3C
N
Quinine
(XXIV)
NH
O
CH3
HO
Fialuridine (Anti viral compound)
(XXV)
OH
H3 C
CH 3
Cl
Chloroxylenol
(XXVI)
HN
NH
O
Indigo dye
(XXVII)
Cl O
O
NH
S NH 2
O
OH
Furosemide (Sulpha drug)
(XXVIII)
(f) C=O
(g) C N
50. Draw one possible structure for each of these molecules selecting
any group of your choice for the wild card substituents for
R1
R
A
Ar2 O
Ar1
Ar3
57
H3 C
H3 C
CH 3
H3 C
II
CH3
OH Cl
H2 N
H 3C
CH 3
CH 3 CH 3
H3 C
H3 C
H3 C
III
CH 3
CH 3
IV CH 3
O CH
3
V
CH3
HN
CH3
VI
OCH3
CH 3
CH 3
CH 3
Br
CH 3
N
H3 C
VII
CH 3
CH 3
OH
O
N
O
VIII
H3 C
H3 C
CH 3
CH 3
H3 C CH CH3
3
II
H3 C
H3 C Cl
III
CH 3
OH
CH 3
CH 3
CH3
Cl
O CH
3
IV CH 3
V
53. What are alicyclic compounds? Write at list 10 compounds with
different chemical nature.
(b) Alkene
(c) Alkyne
(d) Ether
58
(f)
(g) Thioether
(h) Ester
(i)
(j)
sec-Amide
(l)
Aromatic compound
Acid anhydride
(k) t-Amide
t-Amine
B.
C.
56. What bond angles do you expect for each of the following and
what kind of hybridization do you expect for the central atom
in each case?
A.
B.
C.
D.
H3 C
I
Cl
H 3C
H2 C
CH 2
H2 N
II
OH
COOH
IV
CH 3
VI
CH2
CH 2
HN
XI
VIII
VII
NH 2
IX
III
S
XII
CH+2
N
XIII
59
H3 C
H3 C
CH3
CH 3
CH 3
CH3
XIV
CH 3 H
H
H
H
CH 3
XV
H
C
III
IV
H2 C +
H2 C
II
H3 C
VI
CH 2
VII
CH 2
VIII
H2 N
H3 C
IX
CH 2
CH 2
X
CH 2
XI
H
N
XIII
XIV
N
XV
XII
IV
H3 C
O
60
CH 3
VII
V
H3 C
O
VI
CH 3
VIII
H3 C
O
CH 3
IX
H3 C
CN
H
N
CN
H3 C COOH
XI
XII
Cl
XIII
XIV
XV
60. Classify the following molecules into aromatic, anti aromatic
and non aromatic compounds.
II
IV
III
VI
VIII
VII
IX
.
XIII
XII
XI
XIX
XX
XXIV
XIV
XV XVI
XVII
XXII
XXI
XVIII
XXIII
H
N
H
N
XXV
XXVI
XXVII
XXVIII XXIX
N 2Cl
XXXI
XXX
HO
OH
Squaric acid
XXXV
XXXII
N
+
Sydnone Ph
XXXVI
XXXIII
XXXIV
Tropone
XXXVII
Tropolone
XXXVIII
OH
61
O
Pyrylium ion Phenalenyl anior
XXXIX
XL
N
H3 C
N+
XLV
XLVI
O
Ph
Ph
XLVIII
XLIX
62
Heptalene
XLII
CH 3
XLIV
XLIII
Pentalene
XLI
XLVII
Answers
01
Subjective Approach
63
H3 C
CH 3
H3 C
CH3
CH 3
CH
CH3 3
CH3
H3 C
H 3C
CH 3
64
CH 3
H3 C
H3 C
CH3
CH 3
CH 3
CH 3
CH 3
H3 C
CH 3
H3 C
H3 C
CH 3
CH 3
H3 C
CH 3
H3 C
CH 3
CH3
CH 3
H3 C
CH 3
CH 3
H3 C
CH 3
CH 3
13. Those structures are not a ccording to geometry and may
create confusions so better representa tions a re
H
OH
N CH 3
H3 C
NH 2
65
66
Cl [Ne]3 s,3 p5
I [Kr]5 s4d10 5p5
67
H
O
C
C
H
H
H
H
H
H
O
Formic acid Formaldehyde Methanol
31. If there wa s a full negative charge on the oxygen a tom, the
dipole moment would be
C
68
33. CH
, CH
HO Br , I Cl ,
3 Cl
3 NH2
, CH3 Mg Br a nd NH 2 OH
CH
3 OH
Compound Use
CH3
01
CH 3
02
NH 2
03
04
Antiseptic in surgery
Phenol
69
05
CH3
CH 3 CH 3
H3 C
CH 3
Iso-octane
CH3
CH 3
H3 C CH 3
OH
06
CH 3
07
08
OH
O
HO
HO
OH
Glucose
CH2 OH
Ordinary sugar
H H O H HOH 2 C O H
isolated from
H HO
O
CH 2 OH sugarcane or
HO OH H
OH H
sugar beet
H OH
(Sucrose)
H2 C
HO
09
H 3C
N
Quinine
HS
10
70
SH
H 3C
H3 CO
(A)
(B)
OCH3
(C) H3 CO
OCH3
+
N
(A)
(B)
O
O
O
NH
(C)
N
39. Proba ble formulas are GeCl4 , AlH3 , CH2 Cl2 , SiF4 & CH3 NH 2,
AlCl3 , CF2 Cl 2 , NI3 , PH3 .
H3 C
H3 C
CH 3
H3 C
CH 3
O
H3 C
H3 C
Cl
CH 3
71
(E)
OH and
O
H ,
NH2 ,
and
NH 2
,
OH
H
N
and
Ionic bond
+
43. H3 C O Na
Covalent bond
72
Thiol
(II)
(III)
Acetal
(IV)
(V)
Imine
(VI)
(VII)
(VIII)
(IX)
(X)
(XI)
(XII)
(XIII)
(XIV)
(XV)
(XVI)
(XVII)
(XVIII)
(XIX)
73
(C)
(D)
H3 C
H3 C
H3 C
H3 C
(E)
(B)
CH 2
H 3C
Cl or
Cl
H3 C
CH
CH 3
H 3C
OH or
CH 3
HO
H3 C
(F)
CH 3
(G)
H3 C
O
O
50. There are of course ma ny possible structures. A could be
heteroatom or a structural fragment while Ar could be a ny
of a very large number of substituted benzene rings or even
other types of a romatic rings. Four membered rings could
ha ve A = O, NH, CO, SO2 or even alkene while the R1 & R2
could be sa me or different. To make such structure a lwa ys
be ca reful tha t molecule must follow octet rule.
74
COOH
NH 2
Ph
CH 3
CH 3
CH 3
HN
H2 C
Ph
OCH3
S
COOH
CHO
OH
CHO
O
Cl
OH
O
O
Secondary C Tertiary C
Quaternary C
II
III
IV
VI
VII
VIII
10
75
Primary H
9
Secondary H
2
Tertiary H
1
II
15
III
IV
53. Alicy clic com pounds a re simply the cyc lic a lip ha tic
compounds (Cyclic + Alipha tic), which a re commonly
cycloalkane, cycloalkene, cycloa lkyne, cyclic ether, cyclic
secondary a mines, cyclic tertia ry amine, cyclic ester, cyclic
ketones, cyclic amide, cyclic acid anhydride.
54. Structures are
(a)
(b)
(c)
O
O (i) O
(h) O
55. A. H3 C
CH 3
B. H C
2
H
N
CH 3
(d)
(e)
(f)
H
N
CH3
(j) O
(k) O
(g)
(l)
(m)
CH 2
C. H C
2
CH 2
H3 C
57.
sp
CH 2
sp 2
76
sp2 sp
C
H
sp2
II
sp 2
2
H2 N
sp sp3
H 3C
sp
OH
H2 C
sp
sp
sp 2
CH 2
sp 2
sp 2
sp3
O
sp
sp
CH 3
IV
All sp 2
VII
All sp 2
VI
sp 2
Cl
III
All sp 2
V
COOH
HN
sp3
XI
S
XII
All sp 2
IX
NH 2
All sp2
(X)
CH +2
CH 2
sp 2
All sp 2
VIII
sp 3
sp2
sp 2
sp3
N
All sp2
XIII
CH3
CH 3 H
H3 C
CH 3
H
H
CH 3
H3 C
CH3
H CH 3
3
All sp
All sp3
XIV
XIV
58. Overa ll sha pe of molecules a re
Com. Shape
Com.
Shape
Planner
II
Non-Planner
III
Non-Planner
IV
Planner
Non-Planner
VI
Non-Planner
VII
Planner
VIII
Planner
IX
Planner
Planner
XI
Planner
XII
Planner
XIII
Planner
XIV
Planner
XV
Planner
77
78
Exercise
01
Objective Approach
Single Correct Questions (SCQ) :
1. First organic compound generated in 1828 by Friedrich wohler
is
+
(B) N H 4 O CN
(A) CO 2
O
(C) H 2 N - C- NH 2
(D) H 2 N - C- NH 2
(B) 2,4,6
(C) 3,6,9
(D) 4,6,8
79
(B) 15
(C) 14
(D) 16
(B) C 14 H10
(C) C 14 H12
(D) C 12 H12
is :-
(B) 15
(C) 12
(D) 13
H
O
N
COOH
Penicillin
(A) Amine
(B) Amide
80
(B) 5, 1, 1, 1
(C) 5, 1, 0, 1
(D) 5, 1, 1, 0
(B) 20, 2, 1
(C) 15, 4, 0
(D) 15, 4, 1
compound
are -
(A) 5, 6
(B) 6, 6
(C) 5, 7
(D) 4, 7
OH
(B) 5
(C) 6
(D) 4
is
(B) Alkene
(C) Alkyne
(C)
(B)
N
H
(D)
81
(B) sp2
(C) sp3
(D) None
(B)
(D)
(A)
N
H
(B)
(C)
(D)
O
20. Which of the following do not have bridge head carbon in bicyclo
compound.
(A)
(B)
(C)
(D)
82
(B)
(C)
(D
O
CH 3 C CH 2 CH 3
(B)
(C)
(D)
(A)
(B)
OH
(C)
(D)
O
O C CH 3
COOH
(A)
(B)
(C)
(D)
(A)
(C)
(B)
+
(D)
83
(B) Pentane
(D) 2, 3-Dimethylbutane.
(B) Cyclobutane
(C) Cyclopentane
(D) Cyclohexane
[AIEEE-2002]
(B) CH3 CH 2 OH
(C) CH 3 COCH 3
(D) CH 2 = CH - CH 3
(D) diketones
[IIT-2003]
(A) H 2 C = CH - C N
(B) HC C - C CH
(C) H 2 C = C = C = CH 2
(D) H 2 C = CH - CH = CH 2
(B)
O
(C)
84
(D)
(B) 6
(C) 6
(D) 8
[IIT-2014 (Advanced)]
List-I
(P)
List-II
1.
p-d antibonding
85
2.
d-d bonding
(R)
3.
p-d bonding
(S)
4.
d-d antibonding
Codes:
R
S
3
4
1
2
1
4
3
2
1 2 3
4
38. In the compound H2 C = C = CH CH 3 , the hybridization of 1st
(A)
(B)
(C)
(D)
P
2
4
2
4
Q
1
3
3
1
[BHU 2003]
(A) sp3-sp
(B) sp3-sp3
(C) sp2-sp
(D) sp2-sp2
(A) 5 , 7
(B) 9 , 3
(C) 3, 4
(D) 9, 9
(A) C 2 H2
(B) C 2 H 4
(C) C 2 H6
(D) C 2 H 2 Br2
86
(B) 14, 4
(C) 15 , 4
(D) 16, 4
[DPMT 2007]
44. W hich one of the follow ing does not have sp 2-hybridized carbon?
[JCECE (Med.) 2008]
(A) Acetone
(C) Acetonitrile
(D) Acetamide
CH
1
(B) sp3 , sp 2 , sp
(A) sp3
(B) sp2
(C) sp
(D) sp3 d
is:
N
[BHU (Mains) 2008]
(B) 3
(C) 4
(D) 1
87
(C) CH3 CH 2 OH
(D) CH 3 CH = CH 2
CH3
CH 3 C CH = CH CH C
6
5
7
4
3
2
CH 3
C 2 H2
C6H 6
C2H 6
(A)
(B)
(C)
(D)
(B) CH 3 - C C - CH 3
(A) Anthracene
(B) Tropolone
(C) Aniline
88
(C) CH3 - C CH
(D) H 2 C = C = CH2
(D) ps and pp
(B) Ethyne
(C) Ethene
(D) Ethanol
89
(A) Alcohol
(B) Enol
(C) Ester
(D) Ether
(B) Aldehyde
(C) Amine
90
OH
O O
HO
OH
Vitamin C
is:
(C) 3 amine
(D) 2 amide
(B) Amine
(C) Oxime
(D) Hydrazone
64. Which functiona l group is present
O
EtO
S N N CH 3
N
O
N
N
N
H (Viagra)
CH3O
(A) Amide
(B) Sulphonamide
is
Via gra
(C) Amine
(C) Ester
65. Which functiona l group is present in sulpha drug
H
O
Cl O
S NH 2
COOH
(A) Sulphonamide
(C) Amine
(D) Alcohol
(B) Acetaldehyde
(C) Propanal
(D) Pentanone
91
(B) 2,3-Dimethylbut-2-ene
(C) 3,3-Dimethylbutyne
(D) 3,3-Dimethylbut-1-ene
(B) Butan-2-amine
(C) Butan-2-one
(D) 2-Chlorobutane
OH
(3)
OH
(C)
HO
(D)
N
H
N (3)
H
(8)
(D)
(8)
Cl
92
(B)
+ Cl
(C)
(D)
(B)
(C)
(D)
(A)
(B)
O
(C)
(D)
(A)
(B)
(C)
(D)
(A)
(B)
NC
(C)
HO
HO
CN
(D)
93
(A)
(B)
(C)
(D)
(A) +N
(B)
(C) +N
(D) + S
+N
Tub shaped
(B)
non-planner
(C)
Planner
(D) HC CH Planner
(B) sp2
(C) sp3
(D) dsp2
94
95
is a aromatic compound.
96
Column - II
(P) Aliphatic compound
(Q) Aromatic compound
OCH 3
(C)
(D)
Column - II
(A)
(P) Aliphatic
(B)
(Q) Aromatic
(C)
(R) Alicyclic
(D)
(S) Heterocyclic
(T) Homocyclic
97
O
Paracetamol
95. Functional group present in paracetamol is
HO
(A) Alcohol
(B) Amine
(C) Ketone
(D) 2 amide
OH
H 2 /Ni
O
NH 2 OH
Cu
II
Nylon-6
NOH
H
III
IV
H 2O
Polymerization
H+
N
O
V
98
is
+
+
is
O
N
O
HO
O
OH
99
Answers
01
Objective Approach
01.
(C) 02.
(D) 03.
(B)
04.
(B)
05.
(B)
06.
(B)
07.
(C) 08.
(A) 09.
(C) 10.
(B)
11.
(D) 12.
(A) 13.
(B)
14.
(A) 15.
(D)
16.
(A) 17.
(A) 18.
(D) 19.
(C) 20.
(C)
21.
(C) 22.
(C) 23.
(B)
24.
(B)
25.
(B)
26.
(C) 27.
(A) 28.
(B)
29.
(A) 30.
(A)
31.
(A) 32.
(B,C) 33.
(B)
34.
(B)
35.
(B)
36.
(A) 37.
(C) 38.
(C) 39.
(B)
40.
(C)
41.
(C) 42.
(C) 43.
(A) 44.
(C) 45.
(D)
46.
(B)
47.
(C) 48.
(C) 49.
(A) 50.
(D)
51.
(B)
52.
(B)
53.
(D) 54.
(A) 55.
(A)
56.
(B)
57. (A,B,C) 58. (A,B,D) 59. (A,B,C) 60. (A,B,C)
61. (A,C,D) 62. (A,B,D) 63. (A,C,D) 64. (A,B,C) 65. (A,B,C)
66. (A,B,C) 67. (A,B,D) 68. (A,B,C) 69. (B,C,D) 70. (A,B,D)
71. (A,B)
72. (A,B,D) 73. (A,B,D) 74. (A,B,D) 75. (A,C,D)
76. (B,C,D) 77. (A,B,C) 78.(A,B,C,D)79. (B,C,D) 80. (A,B,C,D)
81. (B,C)
82.
(A) 83.
(E)
84.
(A) 85.
(B)
86.
(A) 87.
(A) 88.
(B)
89.
(A) 90.
(D)
91.
(A) 92.
(B)
93. (A-P,S ; B-P,R,T ; C-P,R ; D-Q,S,T)
94. (A-Q,T ; B-P,R,T ; C-P ; D-Q,S)
95.
(D) 96.
(C)
97.
(D) 98.
(A) 99.
(4)
100. (6)
101. (12)
102. (6)
100
Unit
Nomenclature of organic
compounds
In this section you are going to learn the basic concepts of IUPAC
nomenclature. Here you are going to learn how organic molecules
are named along with some common na mes which you will
regularly encounter in due course of organic chemistry
101
Section
Alkyl groups
The concept of alkyl group is very much important in organic
chemistry a s it is the backbone of ca rbon skeleton of orga nic
molecule. As every organic molecule is derived from alkane, so the
alkyl group is too derived from alkane itself. If a hydrogen atom is
removed from an alkane then the partial structure that remains is
called as a lkyl group.
Alkane - H = Alkyl group
It is important to note that, as hydrogen is removed from alkane
i.e. all valency of carbon is not fulfilled, alkyl groups are not stable
compounds but they are simply a part of large compound.
Alkyl groups are named by repla cing the -ane ending of the
parent alkane with an -yl ending. For example, the removal of a
hydrogen from methane (CH4 ) generate a methyl group (-CH3 ) and
removal of hydrogen from ethane (CH3 CH3 ) generate ethyl group
(-CH2 CH3 ). Similarly removal of a hydrogen atom from the end
carbon of any n-alkane gives corresponding n- alkyl group such as
Methane - H = Methyl group (-CH3 or -Me)
Ethane - H = Ethyl group (-CH2 CH3 or -C2 H5 or -Et)
n- Propane - H = n-Propyl group (-CH2 CH2 CH3 or -Pr)
n- Butane - H = n-Butyl group (-CH2 CH2 CH2 CH3 or -Bu)
102
H3 C
n-butyl
H3 C
Iso-pentyl
H3 C
CH 3
sec-butyl
103
CH 3
H3 C
H3 C
CH 3
CH 3
tert-butyl
tert-pentyl
It is important to note that n, iso & neo alkyl group are generally
used for removing hydrogen from primary carbon, sec for secondary
carbon and tert for tertiary carbon with an exception in iso-propyl
where hydrogen is removed from secondary carbon. It is because
of the reason that, here there is a tie between iso a nd sec and as
alphabetica lly i comes first before s, iso is considered.
H3 C
CH 3
iso-propyl
H 3C NH 2
Methyl amine
H 3 C Cl
Methyl chloride
104
105
Section
106
CH 3
H 3C
Compound with
0 substituents
Br
F
Compound with
2 substituents
CH 3
H 3C
CH 3 Cl
Compound with 2 substituents
Br
F
Cl
H3 C
Compound with
4 substituents
2 0 Prefix
-F
Fluoro
-Cl
Chloro
-Br
Bromo
-I
Iodo
-NO2
Nitro
-NO
Nitroso
-R
-OR
-Ph
Phenyl
107
H3 C
CH 3
No 1 Prefix
H3 C
1 Prefix-cyclo
No 1 Prefix
1 Prefix-cyclo
1 Prefix-Bicyclo
1 Prefix-Spiro
1 Prefix-Bicyclo
1 Prefix-Bicyclo
CH 3
When two or more atoms are common between the two rings
then such compounds are called as bicyclic compounds but when
one atom is common between the two rings then it is called as spiro
cyclic compound. Bicyclic compound has 2 bridge head carbon
connected to each other.
Bridge head C
Bridge head C
Bridges
Spiro cyclic
compound
108
Bridge head C
Bridge head C
Word root
C1
Meth
C2
Eth
C3
Prop
C4
But
C5
Pent
C6
Hex
C7
Hept
C8
Oct
C9
Non
C10
Dec
For more than 10 carbons some special word such as Undec for
C11 , Dodec for C12 and so on is used which is less common.
109
Secondary suffix
oic acid
Sulphonic acid
Ester (COOR)
oate
oyl halide
Amide (CONH2)
amide
Nitrile (CN)
nitrile
Aldehyde (CHO)
al
Ketone (CO)
one
Alcohol (OH)
ol
Amine (NH2 )
amine
110
Section
H 3C
1 2 3
CH 3
Incorrect
CH 3
CH 3
5
H3 C
2
1CH 3
Incorrect
4
CH 3
111
H3 C
1 CH 3
3
2 4
CH 3
Incorrect
CH 3
CH 3
1
H 3C
2
7
CH 3
6
CH 3
Correct
2
H3 C
3
CH3
1
CH 3
4
CH 3
8
7 CH3
Incorrect
8 C in parent chain & 1 subst.
H3 C 2
4
6
8
1
3
5 7 CH 3
CH 3
correct
8 C in parent chain & 1 subst.
112
Cl
H3 C 2 3 4 5 6 Cl
H3 C 5 4 3 2 1 Cl
1
6
Incorrect
Correct
In first ca se the locant is 2,6 but in second case locant is 1,5.
CH 3
CH 3
Ethyl (E)
CH 3
CH 3
3
3
4
8
4
8
6
2
6
H3 C 2
H
C
3
5 7
5 7
1
1
CH 3
CH 3
Methyl (M)
Incorrect
Correct
Here ethyl comes alphabetically before methyl so, ethyl must
get minimum number.
5
H3 C 7
8
Complex substituent H 3C
Cl
3
2 1 Cl
CH 3 Simple substituent
Organic
Chemistry
is easy substituents,
by
For assigning
the name
to the complex
the
113
www.CoachMe.co.in
2-Chloroethyl
Cl
5
3
H3 C 7
2 1 Cl
8
2
1 CH
1-Methylethyl H 3C
3
Here for the substituent at position-5, the main substituent is
ethyl on which another substituent Cl is present (Cl is substituent
of substituent). So it is named as 2-Chloroethyl. For substituent at
position-4, the main substituent is again ethyl on which methyl is
substituted at position 1. So it is named as 1-Methylethyl.
6
H 3C
114
Ethyl
1
3 2
1,1-Dimethylethyl
1-(1,1-Dimethylethyl)-4-ethylcyclohexane
1,1-Dimethylethyl
1
3 2
1,1-Dimethylethyl
1,4-Bis-(1,1-dimethylethyl)cyclohexane
115
Section
116
When primary suffix other than ene or yne (i.e. diene, diyne,
triene, triyne etc), is used then at the end of word root an
a is added.
H3 C
1
3
2 4CH 2
Buta-1,3-diene
Cyclohexane
1 Prefix
Word root
1 suffix
117
6 1
Methylcyclohexane
21
Locants:
1,5
(Incorrect)
6 1
1,3
(Correct)
4
5
6 1 Br
2
3
1,3,6
3
4
2 1 Br
6
5
1,2,5
6
5
1 2 Br
43
1,2,4
(Lowest set of locant)
4 5 Cl
2 16
Br
1-Bromo-5-chloro-4-ethyl-2-methylcyclohexane
118
CH 3
3 carbons 4 carbons
1-Cyclopropylbutane
Methylcyclo
propene
H3 C
1-Cyclopropyl
propene
I
H3 C
CH 3
1-Ethyl-5-methyl
cyclopentene
1
Br
2
3-Bromo-1-iodo
Cyclohexene
cyclohexa-1,4-diene
1 CH 3
2
CH3
2
1
3-Methylcyclo
octyne
3
1
2
Cyclooctyne
3
CH 3
1,3-Dimethyl
cyclohexene
CH3
CH 3
H3 C 2 1
Cl
3
119
Methylbenzene
Benzene
carboxylic acid
2-Methylbenzene
carboxylic acid
Benzene
120
Methylbenzene
Cyclohexyl
benzene
CH2
Phenylethene
Phenylethyne
CH3
1 CH
3
2
1-Ethyl-2-Methyl
benzene
121
Section
122
2Suffix
1.
COOH
oic acid
2.
3.
4.
5.
SO3H
Sulphonic acid Sulpho
sulphonic acid
-COOCO- Acid anhydride
oic anhydride
-COOC
Ester
Alkoxycarbonyl oate
& Alkanoyloxy
-COX
Acid halide
Halocarbonyl oyl halide
6.
7.
-CONH2
-CN
Amide
Nitrile
Carbamoyl
Cyano
amide
nitrile
8.
-CHO
Aldehyde
al
9.
-CO-
Ketone
Formyl, aldo
or Oxo
Oxo
Alcohol
Amine
Hydroxy
Amino
ol
amine
10. -OH
11. -NH2
one
123
O
H
NH 2
H3 C
CH 3
Butan-2-one
Propanal
H3 C
CH 3
Butan-2-amine
CH3
H 3C
O
H+H
Carboxylic acid
H3 C
O
CH 3
Acid anhydride
H 2 O
Carboxylic acid
CH 3
H3 C
O
H+H
Carboxylic acid
H 2 O
H3 C
H 3C
Alcohol
H+H
H 3C
NH
H 2 O
H3 C
Primary amine
CH 3
O
H+H
O
H 2 O
Alcohol
CH 3
NH
Amide
CH 3
CH 3
H 3C
O
Ether
H 3C
NH 2 + H NH
NH 3
Primary amine
Primary amine
124
CH 3
CH3
H 3C
Carboxylic acid
O
Ester
Alcohol
O
O
CH 3
NH
Secondary amine
H3 C
NH 2 + H
Primary amine
CH 3
H 3C
N
NH 3
CH 3
Secondary amine
H 3C
Tertiary amine
125
1 N
CH 3
CH 3
N-Ethyl-N-methylethanamide
CH 3
N-Ethyl-N-methylethanamine
126
S.N.
Functional Groups
Secondary suffix
Carboxylic acid
Ester (-COOC)
Carboxylate
Carbonyl halide
Amide (-CONH2)
Carboxamide
Nitrile (-CN)
Carbonitrile
Aldehyde (-CHO)
Carbaldehyde
Cyclohexane
carboxylic acid
CONH 2
Cyclohexane
carbaldehyde
COCl
CN
Cyclohexane
carbonitrile
COOMe
Cyclohexane
Methylcyclohexane
carbonylchloride
carboxylate
Cyclohexane
carboxamide
COOH
Benzene
carboxylic acid
CONH 2
Benzene
carboxamide
CHO
CHO
Benzene
carbaldehyde
COCl
Benzene
carbonyl chloride
CN
Benzene
carbonitrile
COOMe
Methylbenzene
carboxylate
127
2 1
COOH
2-Phenylethanoic
acid
Benzene
carboxylic acid
OH O
H 3 C 5 4 3 2 1 OH
6
3-Hydroxy-5-oxohexanoic acid
Ethanoyloxy
O
128
H3 C 5 4 3 2 1 OH
6
5-Oxohexanoic acid
H 5 4 3 2 1 OH
5-Oxopentanoic acid
COOH
1
2
O 6
H
5 4 3
CH 3
O
3-(1-Oxoethyl)-5-(2-oxoethyl)benzenecarboxylic acid
O
2
3
1 OH
O
3-(N-Methylcarbamoyl)
propanoic acid
CH 3
129
Benzene
OH
NH 2
Phenol
Aniline
130
Section
2.
3.
or
Spiro compounds Fused bicyclic
Bridged bicyclic
131
2
6 1
2
or
7
3
5
5
4
3
4
Bicyclo[2,2,1]heptane
6
10 1 2
3
4
.
76 5
Bicyclo[4,4,0]decane
CH 3
7 CH
1
3
1
6
6
2
2
or
7
3
5 4
5
3
4
1-Methylbicyclo[2,2,1]heptane
H3 C 7
1
2
6
or
2
H 3C
3
5
5 4
4
3
7-Methylbicyclo[2,2,1]heptane
6
10 1 2 3 O
4
765 I
4-Iodobicyclo[4,4,0]dec-1-en-3-one
9
8
Spiro compounds:
(1) Prefix spiro is used followed by alkane corresponding to
the total number of carbon atoms in both ring.
(2) The number of carbon is both the rings, leaving the spiro
atom (a tom joining the rings) is written in bra cket in
ascending order after spiro.
(3) The numbering starts from the atom next to spiro atom in
the smaller ring & proceeds to the la rger ring via spiro
atom.
133
1
8 3 4
7
5
6
Spiro[2,5]octane
CH3
2
1
Cl
8 3 4
5
7
6
1-MethylSpiro[2,5]octane
4 5 1
9
6
8 7
Spiro[4,4]nonane
Cl
2
1
8 3 4
5
7
6
1-Chlorospiro[2,5]oct-4-ene
1
O
8 3 4
7
5
6
Spiro[2,5]octan-4-one
134
Section
Common name
IUPAC name
1.
Marsh gas,
damp fire
Methane
Iso-butane
2-Methylpropane
CH4
CH 3
2.
H3 C
CH 3
CH 3
3.
H3 C
CH 3 Iso-pentane
CH 3
4.
H3 C
CH
CH3 3
Neo-pentane
2-Methylbutane
2,2-Dimethyl
propane
135
5.
Iso-hexane
2-Methylpentane
Neo-hexane
2,2-Dimethylbutane
7.
Benzene
Benzene
8.
Naphthalene
Naphthalene
9.
Anthracene
Anthracene
10.
Phenanthrene
Phenanthrene
Ethylene
Ethene
CH 2
Propylene
Propene
CH 2
Iso-butylene
2-Methylpropene
Allene
Propa-1,2-diene
Acetylene
Ethyne
Methylacetylene
Propyne
H3 C
CH 3
CH 3
6.
H3 C
11.
H2 C
12.
H3 C
CH 3
CH 3
CH 2
H3 C
13.
14.
H3 C
CH 2 C
CH 2
15. HC CH
16. H 3 CC CH
17.
Ethylmethyl
H3 C C C CH 2 CH 3 acetylene
Pent-2-yne
18.
H3 C Cl
Methyl chloride
Chloromethane
19. CH 2 Cl 2
20. CHCl 3
Chloroform
136
Trichloromethane
H3 C
Cl
Methane
tetrachloride
Tetrachloromethane
Ethylchloride
Chloroethane
H3 C
23.
Cl
Iso-Propylchloride 2-Chloropropane
H3 C
Cl
24.
H3 C
25. Cl
26.
CH 3
CH 3
CH 3
CH 3
Cl
H3 C
CH 3
CH3
27. H C
3
28.
Cl
1-Chloro-2-methyl
propane
Tert-Butyl chloride
2-Chloro-2-methyl
propane
Neo-Pentyl chloride
1-Chloro-2,2-dimethyl
propane
Ethylene dichloride
1,2-Dichloroethane
Cl
CH 3
Cl
Iso-Butyl chloride
Cl
29.
H3 C
30.
H2 C
31.
H2 C
Cl
Cl
Cl
Vinyl chloride
1-Chloroethene
Allyl chloride
3-Chloropropene
137
32.
Phenylchloride
Chlorobenzene
Benzyl chloride
1-Chloro-1-phenyl
methane
Benzal chloride
1,1-Dichloro-1-phenyl
methane
Cl
33.
Cl
Cl
34.
35.
Cl
Cl
Cl
Benzo chloride
1,1,1-Trichloro-1-phenyl
methane
Cl
Cl
36. Cl
Cl
Cl Gammexane, Lindane,
Hexachlorocyclo
Benzenehexa
Cl
hexane
chloride(BHC)
OH
37.
H3 C
38.
H3 C
OH
Ethyl alcohol
(Methyl carbinol)
Ethanol
Propyl alcohol
Propan-1-ol
OH
39.
H3 C
CH 3
OH
40.
H3 C
41. HO
138
CH 3
Sec-Butyl alcohol
Butan-2-ol
Iso-Butyl alcohol
2-Methylpropan-1-ol
CH 3
CH 3
42.
CH 3
OH
H3 C
CH 3
CH3
43.
H3 C
44.
H2 C
OH
CH 3
OH
Neo-Pentyl alcohol
2,2-Dimethyl
propan-1-ol
Allyl a lcohol
Prop-2-en-1-ol
Benzyl alcohol
1-Phenylmethanol
OH
45.
46. HC
OH
OH
47.
OH
Ethane-1,2-diol
Propylene glycol
Propane-1,2-diol
OH
48.
H3 C
OH
Trimethylene
OH
glycol
49. HO
OH
OH
OH
O
50.
51.
Propane-1,3-diol
Glycerol
(Glycerine)
Propane-1,2,3-triol
Formaldehyde
Methanal
Acetaldehyde
Ethanal
Propionaldehyde
Prapanal
52.
H3 C
53.
H3 C
139
54.
H3 C
n-Butyraldehyde
Butanal
55.
H3 C
Iso-Butyraldehyde 2-Methylpropanal
CH 3
O
56.
H2 C
Acrolein
Prop-2-enal
Crotonaldehyde
But-2-enal
Dimethyl ketone
(Acetone)
Propanone
Acetophenone
Phenylethanone
Benzophenone
Diphenyl
methanone
Ethyl methyl
ketone
Butanone
57.
H3 C
H
O
58.
H3 C
CH 3
59. Ph
CH 3
60.
Ph
Ph
O
61.
H3 C
CH 3
62.
H3 C
63.
H3 C
64.
H2 C
Methyl propyl
ketone
Pentan-2-one
CH 3 Diethyl ketone
Pentan-3-one
CH 3
O
O
140
CH 3
Methyl vinyl
ketone
But-3-en-2-one
65.
OH
Formic acid
Methanoic acid
Acetic acid
Ethanoic acid
Propionic acid
Propanoic acid
66.
67.
68.
H3 C
OH
O
H3 C
OH
O
H3 C
OH
n-Butyric acid
Butanoic acid
69.
H3 C
OH
70.
H3 C
OH Iso-butyric acid
CH3
2-Methylpropanoic
acid
71.
H2 C
OH
Acrylic acid
Prop-2-enoic acid
72.
H3 C
OH
Crotonic acid
But-2-enoic acid
COOH
73.
COOH
Oxalic acid
Ethane-1,2-dioic acid
Malonic acid
Propane-1,3-dioic
acid
Succinic acid
Butane-1,4-dioic acid
Glutaric acid
Pentane-1,5-dioic
acid
COOH
74.
COOH
COOH
75.
76.
COOH
COOH
COOH
141
77.
Adipic acid
Hexane-1,6-dioic
acid
2-Hydroxy
propanoic acid
COOH
OH
CH 3
Lactic acid
H
79. H
COOH
OH
OH
COOH
Meso-Tartaric acid
78.
COOH
H
OH
d or l
80. HO
H
Tartaric acid
COOH
COOH
81.
Malic acid
HO
COOH
COOH
COOH Citric acid
COOH
82. HO
(2R,3S)2,3-Dihydroxy
butane-1,4-dioic acid
(2R,3R)2,3-Dihydroxy
butane-1,4-dioic acid
Or
(2S,3S)2,3-Dihydroxy
butane-1,4-dioic acid
2-Hydroxybutane
-1,4-dioic acid
2-Hydroxy
propane-1,2,3tricarboxylic acid
83.
H3 C
COOH
Pyruvic acid
2-Oxopropanoic acid
Maleic acid
Cis-But-2-ene1,4-dioic acid
COOH
84.
COOH
COOH
85.
HOOC
Fumaric acid
Trans-But-2-ene
-1,4-dioic acid
COOH
86.
142
Benzoic acid
Benzene carboxylic
acid
87.
88.
COOH
OH
Salicylic acid
COOH
O
O
89.
90.
COOCH 3
OH
2-Hydroxybenzene
carboxylic acid
2-(Ethanoyloxy)
benzene
carboxylic acid
COOPh
OH
Phenyl salicylate
(Salol)
Phenyl-2-hydroxy
benzenecarboxylate
Picric acid
2,4,6-Trinitrophenol
OH
O2N
NO 2
91.
NO 2
CH=CHCOOH
92.
Cinnamic acid
3-Phenyl
prop-2-enoic acid
93.
OCH 3
Methylformate
Methylmethanoate
94.
OCH2 CH3
Ethylformate
Ethylmethanoate
95.
H3 C
OCH 2 CH3
96.
Cl
Ethyl acetate
Formylchloride
(Unstable)
Ethylethanoate
Methanoyl chloride
143
97.
Benzoyl chloride
Benzene carbonyl
chloride
Acetyl chloride
Ethanoyl chloride
98.
H3 C
Cl
99.
Acetic
H3 C
CH 3
O
anhydride
or (CH 3CO )2 O
Ethanoic
anhydride
CH 3 Propionic
O
100. H3 C
anhydride
or (CH 3CH2 CO)2 O
Propanoic
anhydride
101.
Formamide
Methanamide
Acetamide
Ethanamide
Propionamide
Propanamide
104.
Acetanilide
N-Phenyl
ethanamide
105. H 3 CON=O
Methyl nitrite
Nitrito methane
Ethyl nitrite
Nitrito ethane
Methyl amine
Methanamine
NH 2
O
102.
H3 C
NH 2
O
103. H3 C
NH 2
NHCOCH3
106. H C
3
ON=O
107. H 3 CNH 2
144
109.
110.
H3 C
NH 2
H3 CNH
CH 3
H3 C
Ethyl amine
Ethanamine
Dimethyl amine
N-Methyl
methanamine
CH 3
NH
Diethyl amine
CH 3
111. H3 CN
CH 3
H3 C
N
112.
Trimethyl amine
N-Ethyl ethanamine
N,N-Dimethyl
methanamine
CH 3
Triethyl amine
H 3C
N,N-Diethyl
ethanamine
113. H 2 NSO 3H
Sulphamic acid
114. H 3 CSO 3 H
Methylsulphonic
acid
Amino sulphonic
acid
Methanesulphonic
acid
115.
Phenyl sulphonic
acid
Benzene sulphonic
acid
116. H 3 CCN
Methyl cyanide
or Acetonitrile
Ethane nitrile
Phenyl cyanide
or Benzonitrile
Benzene carbonitrile
SO 3H
CN
117.
118. H 3 CNC
119.
H3 C
Methyl iso-cyanide or
Methylcarbyl amine
Ethyl iso-cyanide or
NC Ethyl carbylamine
Methane iso-nitrile
Ethane iso-nitrile
145
Phenyl iso-cyanide or
Phenylcarbyl amine
120.
121.
122.
123.
O
O
epoxide
Oxirane
Trimethylene
oxide
Oxetane
Tetrahydrofuran
(THF)
Oxolane
Dioxane
1,4-Dioxacyclo
hexane
Trioxane
1,3,5-Trioxacyclo
hexane
Toluene
Methylbenzene
Ethylbenzene
Ethylbenzene
124.
125.
O
O O
Benzene iso-nitrile
CH 3
126.
CH 3
127.
H3 C
CH 3
128.
H 3C
129. H3 C
Iso-propylbenzene (1-Methylethyl)
(Cumene)
Benzene
CH 3
Tert-Butyl
benzene
(1,1-dimethylethyl)
benzene
Styrene
Phenylethene
CH=CH 2
130.
146
o-Xylene
1,2-Dimethyl
benzene
m-Xylene
1,3-Dimethyl
benzene
p-Xylene
1,4-Dimethyl
benzene
Mesitylene
1,3,5-Trimethyl
benzene
Carbolic acid
Phenol
Catechol
Benzene-1,2-diol
Resorcinol
Benzene-1,3-diol
Hydroquinone
Benzene-1,4-diol
CH3
132.
CH 3
CH 3
133.
CH 3
CH3
134.
H3 C
CH 3
OH
135.
OH
OH
136.
OH
137.
OH
OH
138.
OH
147
139.
OH
140.
- Naphthol
1- Naphthol
- Naphthol
2-Naphthol
Benzaldehyde
Benzene
carbaldehyde
Salicyldehyde
2-Hydroxybenzene
carbaldehyde
Oil of mirbane
Nitrobenzene
Anisole
Methoxybenzene
Aniline
Aniline
o-Toluidine
2-Methylaniline
m-Toluidine
3-Methylaniline
CHO
141.
142.
CHO
OH
NO 2
143.
OCH3
144.
NH 2
145.
146.
NH2
CH 3
NH 2
147.
CH 3
148
148.
p-Toluidine
4-Methylaniline
o-Cresol
2-Methylphenol
m-Cresol
3-Methylphenol
p-Cresol
4-Methylphenol
Iso-octane
2,2,4-Trimethyl
pentane
Mustard gas
Bis-(2-Chloroethyl)
sulphide
Westron
1,1,2,2-Tetra
chloroethane
155. ClCH CH 2
Westrosol
1,1,2-Trichloro
ethene
156. Cl 3C NO 2
Chloropicrin
tear gas
1,1,1-Trichloro-1nitromethane
Chloretone
1,1,1-Trichloro-2methylpropan-2-ol
CH3
OH
CH 3
149.
OH
150.
CH 3
OH
151.
CH 3
152.
153.
154.
CH 2 Cl
CH 2 Cl
CH2 S CH2
CHCl 2
CHCl 2
CCl 3
157. CH 3 CCH 3
OH
149
158.
CH 3 C
CHCH 3
Triptane
2,2,3-Trimethyl
butane
Isoprene
2-Methyl
buta-1,3-diene
Chloroprene
2-Chloro
buta-1,3-diene
Lewisite
2-chloroethenyl
arsonousdichloride
Pinacol
2,3-Dimethyl
butane-2,3-diol
Pinacolone
3,3-Dimethyl
butan-2-one
CH 3 CH 3
159.
CH 3
H2 C=CCH=CH 2
Cl
160. CH C=CHCH
2
2
ClCH
161.
HCAsCl 2
CH 3 CH 3
162. CH 3 C CCH 3
OH OH
O
163.
CH 3 C
CH3
CCH 3
CH 3
164.
CHO
COOH
Glyoxalic acid
2-oxoethanoic acid
Pivaldehyde
2,2-Dimethyl
propanal
CH 3
165.
CH 3 C CHO
CH 3
O O
166. CH CCCH Dimethylglyoxal
3
3
O O
167.
150
PhCCPh
Benzil
Butan-2,3-dione
1,2-Diphenyl
ethane-1,2-dione
169.
CHO
CHO
Glyceraldehyde
2,3-Dihydroxy
propanal
Glyoxal
Ethanedial
CHO
Methylglycol
(Pyruvic aldehyde)
170. CCH3
O
H3 C
171.
C=CHCCH=C
H3 C
H3 C
172. H C
3
CH 3
CH 3
C=CHCCH 3
Phorone
Mesityloxide
173. H 2 C=C=O
2-oxopropanal
2,5-Dimethyl-4en-3-one
4-Methylpent
-3-en-2-one
Ketene
Ethenone
Carbonic acid
Carbonic acid
174.
HOCOH
O
175. CH CCOOH Pyruvic acid
3
OH
176.
PhCHCOOH
Mendalic acid
CH 3
H2 NCHCOOH
179. H 2 N COOH
Alanine
Carbamic acid
2-oxopropanoic acid
2-Hydroxy-2-Phenyl
ethanoic acid
Aminoethanoic acid
2-Amino
propanoic acid
Carbamic acid
151
180.
181.
COOH
OO
ClCCCl
182. H NCONH
2
4
O
Glycolic acid
2-Hydroxy
ethanoic acid
Oxalyl chloride
Ethanedioyl
dichloride
Ammonium
carbonate
Ammonium
carbonate
Acetoacetic
ester
Ethyl-3-oxo
butanoate
184.
Phosgene
Carbonyldichloride
Urea
Carbamide
Indole
Indole
Pyridine
Pyridine
188. N
H
Pyrrole
Pyrrole
189.
Thiophene
Thiophene
Furan
Furan
Azulene
Bicyclo[5,3,0]
decapendaene
Cl C Cl
185. H NCNH
2
2
N
H
186.
187.
190.
S
O
191.
192. H2 N
152
SO 3H
Sulphanilic
acid
4-Aminobenzene
sulphonic acid
193.
O
194.
OH
Tropone
Cyclohepta-2,
4,6-trienone
Tropolone
2-Hydroxycyclo
hepta-2,4,6-trienone
OH
HO
O
195.
Phenol
phthalin
O
H Cl
Cl
Cl
Cl
196.
Cl
197.
N N
DPT
Hydrazo
benzene
3,3-Bis-(4-Hydroxy
phenyl) Isobenzo
furan-1-one
1,1,1-Trichloro-2,
2-Bis-(4-chloro
phenyl)ethane
1,2-Diphenyl
hydrazine
H H
OH
O2N
NO 2
198.
O
Picric acid
2,4,6-Trinitrophenol
mcpba
3-chloroperbenzene
carboxylic acid
O-toluic acid
2-Methylbenzene
carboxylic acid
m-toluic acid
3-Methylbenzene
carboxylic acid
NO 2
COOH
199.
Cl
200.
COOH
CH 3
COOH
201.
CH 3
153
p-toluic acid
4-Methylbenzene
carboxylic acid
Phthalic acid
Benzene-1,2-di
carboxylic acid
Isophthalic acid
Benzene-1,3-di
carboxylic acid
Terephthalic acid
Benzene-1,4-di
carboxylic acid
Anthranilic acid
2-Aminobenzene
carboxylic acid
207. N
H
Pyrrolidine
Pyrrolidine
208. N
H
Piperidine
Piperidine
Morpholine
Morpholine
Aziridine
Aziridine
202.
CH 3
COOH
203.
COOH
COOH
204.
COOH
COOH
205.
COOH
COOH
NH 2
206.
209. N
H
210.
N
H
154
1,2-Diphenylethene
Urotropine
1,3,5,7-Tetraaza
tricyclo [3,3,1,1]
decane
Guanidine
Guanidine
Amidine
Acetamidine
Phthalic
anhydride
Benzene-1,2dicarboxylic
anhydride
Phthalimide
Isoindole-1,3-dione
217.
Cinnamaldehyde
3-Phenylprop-2-enal
Dimethylsulphide
Dimethysulphide
(DMS)
212. N N
N
NH
213. H NCNH
2
2
NH
214. CH CNH
3
2
O
O
215.
O
O
NH
216.
O
CH=CHCHO
219. CH SCH
3
3
O
220.
HCNCH 3
CH 3
Dimethyl
sulphoxide
(DMSO)
Dimethyl
sulphoxide
Dimethyl
formamide
(DMF)
N,N-Dimethyl
methanamide
155
221.
O
N
Barbituric acid
O
OH
222.
O O
HO
HO
Ascorbic a cid
OH
O OH
222.
PhCCHPh
Benzoin
Pyrimidine
-2,4,6-trione
(1,2-Dihydroxyethyl)
-3,4-dihydroxy
furan-2-one
2-Hydroxy-1,2diphenylethanone
156
Section
08
Degree of unsaturation
Degree of unsatura tion (DU) is very importa nt in orga nic
chemistry as it helps to predict different structures for any molecular
formula. It is also called Double bond equivalent (DBE) or Index
of hydrogen deficiency (IHD). Degree of unsaturation is simply
the hydrogen deficiency index from a ny acyclic sa tura ted
hydrocarbon.
We know that formation of a bond occur by loss of two hydrogen
atoms from adjacent position, for the formation of a triple bond
four hydrogen atoms are removed from adjacent position, loss of
two hydrogen atoms also lead to the formation of a cyclic system if
they are not removed from adjacent position. So one bond or one
ring is equal to 1 DU. So DU is equal to sum of bonds a nd rings
in the structures. Such as
Structure
DU
Structure
DU
157
OH OH
HO
OH
(2C + 2) H X + N
2
158
H3 C
H 3C
CH 3
Hexane
CH 3
H3 C
CH 3
2-Methylpentane
H3 C
CH 3
CH 3
3-Methylpentane
CH 3
CH
CH 3 3
CH 3
2,2-Dimethylbutane
H 3C
CH 3
CH 3
2,3-Dimethylbutane
159
H2 C
CH 3 H2 C
Pent-1-ene
1
H 3C
CH 3
CH 3
2-Methylbut-2-ene
4
CH 3
CH 3
Pent-2-ene
2
CH 3
CH 3
2-Methylbut-1-ene
3
H 3C
CH 2
CH 3
3-Methylbut-1-ene
5
CH 3
H 3C
CH 3
Cyclo
pentane
6
CH 3
CH 3
Ethylcyclo 1,1-Dimethyl
1,2-Dimethyl
cyclopropane cyclopropane
propane
9
8
10
Example 4: Write all the possible structures with molecular formula
C4H6.
Methylcyclo
butane
7
160
CH 3 H C
CH 3 H C
O
CH 3
3
3
O
2-Methoxy
Ethoxyethane
1-Methoxypropane
propane
H3 C
CH3
H 2C
OH
Prop-1-en-2-ol
2
H2 C
OH
Prop-2-en-1-ol
3
OH
CH 3
H
Propanal
4
H3 C
CH 3
Propanone
5
CH 3
2-methyloxirane
7
Oxetane
8
Cyclopropan-1-ol
6
H3 C
O
CH 2
Methoxyethene
9
Limitations of DU:
Calculation of DU is very much important to draw structure of
any compound with known molecular formula but it has some
limitations such as
161
162
Section
09
CH 3
4
CH 3
3
1
H3 C 2
CH 3
1
1
H3 C
H3 C
2
2
CH 3
1
Example 1:
In pentane there are two types of ca rbon (two 1 0 and three 2 0
carbon). But when we carefully analyze this molecule we find that
replacement of one H by any atom or group such as Cl from the
carbon skeleton leads to three different products.
Cl
CH 3 H
CH 3
H3 C
+Cl Cl
H 3C
CH 3
Pentane
1-Chloropentane 2-Chloropentane
Cl
H 3C
CH3
3-Chloropentane
163
CH 3 or H 3 C
2-Chloropentane
CH 3
Cl
CH 3
H3 C
3-Chloropentane
164
CH 3
Cl
H 3C
+
CH3
Cl
2-Chloro-2-methyl 1-Chloro-2-methyl
butane
butane
H3 C
165
Benzene
Nitrobenzene
Cl
Cl
Conc. H 2 SO 4
Cl
NO 2
Cl
+
NO 2
Chloro
1-Chloro-2-nitro
NO 2
1-Chloro-3-nitro
benzene
benzene
1-Chloro-4-nitro
benzene
benzene
Benzene on nitration gives only one product so all hydrogens
in benzene are identical whereas chlorobenzene on nitration gives
three different products so three types of chemically different
hydrogens are present in chlorobenzene.
HNO 3
CH 3
Conc.H 2SO 4
NO 2
HNO 3
CH3
CH 3
CH 3
+
NO 2
CH 2 Cl
NO 2
Cl 2 /Light
166
H3 C
&
are same
O
O
H3 C
CH 3
H 3C
CH 3
&
CH 3
H 3C
are different
167
Exercise
02
Subjective Approach
01. What are the five basic components which are alwa ys used to
write the IUPAC nomenclature of any organic molecules and
a lso write the role which they pla y in na ming orga nic
compounds?
02. Name the prefix which is used for following substituents- F, Cl,
Br, I, OCH3 , OC2 H5 OR, NO, NO2 , C6 H5 , CH3 , C2 H5
03. Name the suffix which is used for following functional groupscarboxylic acid, sulphonic acid, ester, acid halide, amide, nitrile,
aldehyde, ketone, alcohol, amine.
04. What is difference between phenyl and benzene? When should
we use phenyl and when should we use benzene in writing the
nomenclature?
05. What is correct IUPAC nomenclature given for n propyl, iso
propyl, n butyl, iso butyl, sec butyl, tert-butyl and neo-pentyl
group?
06. Write the IUPAC nomenclature of these common compoundsn butane, iso buta ne, neo-pentane, a cetone, iso butene,
formaldehyde, acetic acid.
168
1,1-Dibromo-3-ethyl-4-flourohexane
B.
4-Ethyl-2-methyl-1-propylcyclohexane
C.
6-Chloro-4-ethyl-5-methylhept-5-en-1-yne
D.
3-Methylcyclohex-1-ene
E.
2-Methylpentane-2,4-diol
09. Select the main chain which is used as a principal chain or word
root for naming compounds?
CH 3
CH 3
H 3C
H3 C
H3 C
H3 C
CH 3
CH 3
CH 3
CH 3
II
CH 3
H 3C
H3 C
H3 C
H3 C
CH 3
CH 3
CH 3
CH 3
II
CH 3
CH 3
H3 C
H3 C
NO 2
I
MeO
CH 3
H3 C
Cl
CH 3
II
169
H3 C
H3 C
Br
CH 3
II
MeO
H3 C
ON
Br
CH 3
Cl
CH 3
IV
CH3
Cl
O2N
CH 3
III
CH 3
Cl
CH 3
CH3
Br
Br
Cl
NO 2
V
Br
CH 3
Cl
NO 2
VI
CH 3
Br
H3 C
NO 2
I
CH 3
H3 C
CH 3
IV
H3 C
H3 C
Pr
VI
CH 3
Et Et
Pr
VII
CH 3
Me
CH 3
H3 C
CH 3
H3 C
H 5C 2 Br
III
170
Cl
II
CH 3
CH 3 O
H3 C
CH 3
CH 3O
H3 C
CH 3
Et Et
CH 3
Me
Bu
Pr
VIII
H3 C III
H3 C
H 3C
IV
CH 3
H3 C
II
H 3C
CH 3
CH 3
CH 3
CH3
CH 3
VI CH 3
CH 3
CH3
CH 2
H3 C
CH CH 3 CH 3
CH 3 3
I
CH 3
III
II
H3 C
CH
CH 2
CH 3
CH 3
CH 3
IV
171
CH3
CH 3
CH 3
H 3C
H 3C
CH3
H 3C
CH 3
CH 3
CH 3
I
II
27. Write the IUPAC name of following compounds.
Cl
HC
CH 3
OH
H3 C
O
H3 C
O
OH
II
CH3
III
CH 2
NH 2
CH 2 CH 3 CH 3 CH 3
V
IV
O
H3 C
CH 3
H3 C
172
III
CH 3
H3 C
CH 3
II
CH 3
O
O
CH 3
CH 3 O
CH 3
O
H3 C
O
CH3 IV
CH 3
Cl
H3 C
CH 3
O
I
CH 3 O
H3 C
III
O
CH3 II
O
O
CH 3
O
CH 3
H3 C
O
O
IV
CH 3
CH 3
H3 C
CH3
H3 C
Cl Cl
Cl
CH 3
CH 3
CH 3
Cl
Cl
II
Cl
Cl Cl
CH 3
III
31. Name the following halides according to IUPAC system and
classify them as alkyl, allyl, benzyl (primary, secondary, tertiary),
vinyl or aryl halides:
173
CH3 CH = CHC(Br)(CH 3 )2
(J)
p - ClC 6H 4 CH 2 CH(CH 3 )2
(O)
(P)
CH 3 CHCH 3
F
(R)
Cl
(S)
(T)
CH3
CH 3CCH 2CH 2CH2 Cl
OH
CH 3CHCH 2 CHCH 2 CH 3
CH3
Cl
174
Cl
(V)
CH 3 CH 2
OH
NO 2
(W)
Br
(X)
(Y)
CHO
NO 2
COOH
(Z)
F
(J)
175
(L)
(M)
(N)
OH
(O)
OH
(P)
(Q)
Cl
HO
(R)
(S)
(T)
CH2 CH 3
CH 3
(U) CH 3CH2 CHCH2 CHCH 2 CH 3
CH2 CH 3
CH3
176
(Y) H2 C
OH
Br
(Z) H3 C
OH
Cl
33. Write IUPAC names of the following compounds:
CH 3
(A) CH 3 CH CH C CH 3
CH 3 OH CH 3
(B)
H3 C CH CH 2 CH CH CH 2 CH 3
OH
OH C 2 H 5
(C) CH 3 CH CH CH 3
OH OH
(D) HO CH 2 CH CH 2 OH
OH
(E)
CH 3
OH
CH 3
(F)
OH
177
(G)
OH
CH 3
OH
(H)
CH3
(I)
CH 3
CH 3 O CH2 CH CH 3
CH3
(J) C 6 H 5 O C 2H 5
(K) C 6 H 5 O C 7 H 15 (n-)
(L)
CH 3 CH2 O CH CH 2 CH 3
CH 3
CH 3
CH 3
(M) CH 3CH2 CHCH 2 CCH 3
CH 3
(S)
178
CH 3 CH 2 CH 2 CH 3
CH 3C CHCH 2 CH 3
CH2 CH2 CH 3
(U)
CH 2 CH 3
CH 3
CH 2 CH 3
(V)
H 3C
(W)
(Y)
H3 C
(X)
CH 2 CH 3
CH2 CH 3
(Z)
CH 2 CHCH3
CH 3
(I)
179
CH 3
CH 3 CHCH 2 CHCHCH 3
CH 3
CH 3
CH 3CHCH 2 CHCH 2 CH 3
CH 3
OH
CH 3
(N)
(O)
CH3
NCH 3
Br
CH 2 CH 3
(P)
OH
(S)
(T)
(U) CH 3 CH 2CHCH3
Cl
CH 3 CH 2CHCH3
NH2
OH
CH 3CHCH 2 CH 2 CH 2 OH
CH 3
CH 3
(W) CH3 CBr
CH 2 CH 3
(Y)
Br
(Z) CH 3CHNH 2
CH 3
35. Write IUPAC names of the following compounds and classify
them into primary, secondary and tertiary amines.
(A) (CH3 )2 CHNH 2
180
CH3 CH 2 CH 2 NHCH 2 CH 2 CH 2 CH 3
(J)
NH 2
(P)
NH 2
H3 C
COOH
COOH
(Q)
NH 2
(R)
COOH
(S)
COOH
(T)
NH 2
181
NH 2
(U)
(V)
CN
COOH
NH 2
(W)
NH 2
(X)
CHO
Cl
NH 2
NH 2
(Y)
(Z)
OH
2,3-Dimethylhexane
(J)
4-isopropyl-2,4,5-trimethylheptane
(K) 4,4-Diethyldecane
(L) 2,2-Dimethyl-4-propyloctane
(M) 4-isobutyl-2,5-dimethyloctane
(N) 4-(1,1-dimethylethyl)octane
(O) 2-Methylbutan-2-ol
(P) 1-Phenylpropan-2-ol
182
2-Methyl-2-bromo-1-propanamine
(J)
N-Ethylethanamine
(K) 5-Methylhexan-1-amine
(L) Methyldipropylamine
(M) N,N-dimethylpentan-3-amine
(N) Cyclohexylethylmethylamine
(O) 5-Ethyl-2-methyloctane
(P) 1,3-Dimethylcyclohexane
(Q) 2,3,3,4-Tetramethylheptane
183
(E) tert-butylamine
(G) 2-Hexyne
(H) 1-Bromo-1-pentyne
(I)
(J)
5-Ethyl-3-octyne
Propargyl bromide
(K) Methylacetylene
(L) Diethylacetylene
(M) Vinylacetylene
(N) di-tert-butylacetylene
(O) Methoxyethyne
(P) Cyclopentylacetylene
(T) 2-Chloroanthracene
(X) o-Nitroanisole
(Y) o-Bromoaniline
(Z) 2,4-Dichlorotoluene
(C) sec-butylamine
184
(H) Cyclopentylcyclohexane
4-tert-butylheptane
(J) 5,5-Dibromo-2-methyloctane
(K) 1-Methylcyclopentanol
(L) 3-Ethoxy-2-methylhexane
(P) 3-Benzylpentane
(Q) p-Bromophenol
(R) m-Chlorotoluene
(S) o-Nitroaniline
(T) 2,5-Dinitrobenzaldehyde
(U) 2-Bromo-4-iodo-1-nitrobenzene
(V) o-xylene
(W) 2-phenylhexane
(B)
BrCH 2 CH 2 CH = CCH3
CH 2 CH 3
CH 3
(C) CH 3CH2 C = CCHCH 3
(D) H C
CH 3
3
CH 3 CH3
Br
(E)
(F) CH3 CH = CHOCH 2 CH 2 CH 2 CH 3
H 3C
(H)
C=C
CH 3CH2
CH2 CH 3
CH2 CH 2 CHCH3
CH 3
CH3
(I)
Br
CH 3
185
(J)
H3 C
C=C
CH 2 CH 3
CH 2 CH 2 CHCH3
(N)
(O)
(P)
Cl
CH
CH 2 CH 2 CH 3
CH 3C CCH 2 CHCH 3
Br
CH 3C CCH 2 CHCH3
CH 2 CH 2 CH 3
CH 3
(Q)
CH 3C CCH 2 CCH 3
CH3
(R)
CH 3CHCH 2 C CCHCH 3
Cl
CH 3
(S)
(T)
CH 3
CH 3
186
(W)
(Z)
CH 3CH2 CH = CCH 2 CH 2 C CH
CH = CH 2
41. Give the systematic name for each of the following compounds:
(A) CH3 C CCH 2 CH 2 CH 2 CH = CH 2
HOCH 2 CH 2
(B)
H
C=C
CH 2 CH 3
H
Cl
(D)
CH 3
(E)
CHBr2
CH 3
(H) H3 C
CH 3
Br
COOH
OH
(G)
(J)
(F)
(I)
Br
OCH 3
(K)
SO 3 H
(L)
CH 2 CH 3
Cl
Cl
187
CH 2 CH 3
(M)
(N)
Cl
Br
(O
Br
NO 2
Br
CN
(P)
(Q)
CH3
Cl
(R) CH3 CH 2 CH 2 C N
CH 3
O O
(T)
CH 3CH2 COCCH3
(W)
NH2
COOH
(Y)
(Z)
O
CHO
O O
COCCH 3
O
(E) CH 3 CH 2 CH 2 CH 2 C N
188
(F)
CH 2 = CHCH2 CNHCH 3
O O
(H) CH 3
CH 2C N
(I)
C H
CH2 COOH
CH 3 CH 2CH 2 CN(CH 3 )2
(J)
CH 3
H
CH 2 CH 2 CH 3
(L)
CH 2 CH 2 CH 2 CH
CH 3
(P)
CH 2 = CHCCH 2 CH 2 CH 2 CH 3
O
(R)
OH
C N
OH
(S)
(T) Br
Cl
HC=O
189
OH
H2 C
(U)
(V) Br
Cl
OH
OH
OH Br
CH
(W)
CH
Br
CH 3
(X) H3 C
H3 C
Cl
CH 2
H3 C
(Y) Cl
OH
OH
CH 2
(Z)
CH 2
(A) H3 C
(B)
H3 C
CH2
(C) H3 C
CH 2
(D)
CH
(E)
H3 C
H 2C
O
(G)
H2 C
(I)
190
Cl
O
CH 2 (F)
H2 C
CH 2 CH 2
Br O
CH 2
(H) H C
3
Br O
N
H
Br
(J)
Cl
N
H
Br O
CH 3
I
N
H
Cl
Cl
(K)
CH 3 (L) O
CH 3
CH 3
(M)
Cl
CH 3
(N)
H3 C
OH
CH 3
CH CH
O
(O)
H3 C
OH (P)
H
N
CH3 O
CH CH
Cl
CH 2
OH
(Q) HC
CH 3
(R)
SO 3H
CH
(S)
(T)
OH
(U)
CH 2
(V)
CN
O
O
H3 C
CHO
COOH
COOH
NH 2
(W)
OH
Br
OH
(X)
O
191
CH 3
OH
(Y)
(Z)
H3 C
O O
44. Write the IUPAC names of following compounds
(A)
(B)
H3 C
NH 2
H3 C
Cl
Cl
OH
(D) HC
(C)
H3 C
(E) HC
O
CH3
H3 C
CH 3
CH 3
OH
H3 C
CH 3
H3 C
CH3
(F)
CH 3
CH 3
Cl
Cl
Cl
Cl
(G)
(H)
H3 C
CH3
CH3
Cl
Cl
Cl
H3 C
(I)
CH 3
CH3 Cl Br
O O
(J)
H3 C
CH 3 Cl
192
CH 3
O O
(K)
OH
(L)
NH 2
O O
(M)
O
H
(M)
(O)
(Q)
(S)
(P)
CH 2 CH 3
O
(R) HCNH
2
O
HCCl
(W)
O
(Y)
O
NH 2
(T)
HCH
(U)
HCNCH3
OH
(V)
OH
O
(X)
OH
O
(Z) HCO
193
Answers
02
Subjective Approach
Prefix
Substituent
Prefix
Fluoro
OR
Alkoxy
Cl
Chloro
NO
Nitroso
Br
Bromo
NO 2
Nitro
194
Iodo
C6 H5
Phenyl
OCH3
Methoxy
CH3
Methyl
OC2 H5
Ethoxy
C2 H5
Ethyl
Secondary suffix
oic acid
Sulphonic acid
Ester (COOR)
oate
oyl halide
Amide (CONH2)
amide
Nitrile (CN)
nitrile
Aldehyde (CHO)
al
Ketone (CO)
one
Alcohol (OH)
ol
Amine (NH2 )
amine
IUPAC name
n propyl
Propyl
iso propyl
1-Methylethyl
n butyl
butyl
iso butyl
2-Methylpropyl
sec butyl
1-Methylpropyl
195
1,1-Dimethylethyl
neo pentyl
2,2-Dimethylpropyl
IUPAC name
n butane
Butane
iso butane
2-Methylpropane
neo pentane
2,2-Dimethylpropane
acetone
Propanone
iso butene
2-Methylpropene
formaldehyde
Methanal
acetic acid
Ethanoic acid
Br
(A)
Br
CH 3
(B)
CH 3
CH 3
(C)
HC
H3 C
H3 C
(D)
Cl
CH 3 OH
(E)
CH3
H3 C OH
CH3
CH 3
H 3C
H3 C
H 3C
CH 3
196
CH 3
CH 3
CH 3
I
10. 2, 4 respectively
CH 3
CH3
H3 C
CH 3
II
CH 3
CH 3
II- 1,1,3,4,5;
III- 1,2,3,5;
IV- 1,2,3,4,5 ;
V- 1,1,2,3,3,4,5,6;
VI- 1,1,2,5,5
13 I- 3-Bromo-5-ethyl-4-nitrooctane
II- 2-Chloro-6-(1-methoxyethyl)-3-methylnonane
III- 5-Bromo-6-(1-methoxyethyl)-3-methylnonane
IV- 1,4-Dimethylcyclohexane
V- 1,2,4-Trimethylcyclohexane
VI- 3-Ethyl-2-methylhexane
VII- 3,5-Dimethyl-4-propylheptane
VIII- 5-Ethyl-3-methyl-4-propylnonane
14. I- 1-Methylethyl;
II- 2-Methylpropyl;
III- 1-Methylpropyl;
IV-2,2-Dimethylpropyl;
V- 3-Methylbutyl;
VI- 1,1-Dimethylethyl
197
CH 3
HC 2 3 4 5 6
1
Hex-4-en-1-yne
CH 3
H 3C
CH 3
CH 3
CH 3
1,4-Bis-(1,1-Dimethylethyl) cyclohexane
198
Cl
Vinyl chloride
25. Structures are
H 2C
Cl
Allyl chloride
O
Ph
Ph
Benzene
Cl
Benzyl chloride
O
Benzil
Benzyne
Benzyl
Benzoyl
26. I)
Benzal
Benzo
II)
27 I)
II)
Pent-4-yn-1-ol
3-Chloro-5-methylcyclohexanol
III) 2-Methylcyclopent-2-enone
IV) 3-Methylcyclobut-2-enamine
V) 4,5,6,8-Tetramethylnona-1,8-dien-3-one
28. I)
II)
1-Methylethylethanoate
1-Methylethyl-2-methylpropanoate
III) 1-Methylethyl-3-methylbut-2-enoate
IV) 2-Methyl 3-oxo-butyl-4-chloropentanoate
29. I)
II)
Ethanoic anhydride
Ethanoic-2-methylpropanoic anhydride
199
1,4-Bis-(1,1-dimethylethyl)cyclohexene
1,1,1-Trichloro-2,2-bis-(4-chlorophenyl)ethane
III) 3,7-Bis-(dichloromethyl)nona-2,7-diene
31.
IUPAC Name
Nature of halide
A.
2-chloro-3-methylbutane
2 Alkyl halide
B.
3-chloro-4-methylhexane
2 Alkyl halide
C.
1-Iodo-2,2-dimethylbutane
1 Alkyl halide
D.
E.
2-Bromo-3-methylbutane
2 Alkyl halide
F.
1-Bromo-2-ethyl-2-methylbutane
1 Alkyl halide
G.
3-chloro-3-methylpentane
3 Alkyl halide
H. 3-chloro-5-methylhex-2-ene
vinyl halide
I.
4-Bromo-4-methylpent-2-ene
3 Allylic halide
J.
1-chloro-4-(2-methylpropyl)benzene
Aryl halide
K.
1-chloromethyl-2-(2,2-dimethyl
propyl) benzene
1 benzyl halide
L.
1-Bromo-2-(1-methylpropyl)benzene
Aryl halide
M. 2-Chlorobutane
2 alkyl halide
N. 1-chloro-5-methylhexane
2 Alkyl halide
O.
Bromocyclohexane
2 Alkyl halide
P.
2-Fluoropropane
2 Alkyl halide
Q.
1-chloropentane
1 Alkyl halide
R.
1-chloro-4-methylcyclohexane
2 Alkyl halide
S.
1-chloro-4-methylpentan-4-ol
1 Alkyl halide
T.
4-chloro-2-methylhexane
2 Alkyl halide
U.
4-chloro-2,6-dimethylhexane
2 Alkyl halide
V.
4-chloro-3-ethylcyclohexanol
2 Alkyl halide
W. 1-Bromo-2-nitrobenzene
200
Aryl halide
1-(1-Brmoethyl)-4-nitrobenzene
1 benzyl halide
Y.
3-Fluorobenzene carbaldehyde
Aryl halide
Z.
3-(1-Fluoroethyl)benzene
carboxylic acid
2 Alkyl halide
32. A.
2-Bromo-3-chlorobutane
B.
1-Bromo-1-chloro-1,2,2-trifluoroethane
C.
1-Bromo-4-chlorobut-2-yne
D.
1,1,1,2,3,3,3-Heptochloro-2-trichloromethylpropane
E.
3-Bromo-2,2-bis-(4-chlorophenyl)butane
F.
1-Chloro-1-(4-iodophenyl)-3,3-dimethylbut-1-ene
G.
Methoxyethane
H. Ethoxyethane
I.
4-Methoxyoctane
J.
1-Propoxybutane
K.
2-(1-methylethoxy)pentane
L.
3-Methyl-1-(1-methylethoxy)butane
M. 1-Methoxypropane
N. Propan-1-ol
O.
4-Propylnonan-1-ol
P.
4-Methyl-5-(1-methylethyl)octane
Q.
6-chloro-4-ethyl-3-methyloctane
R.
5-Methyl-3-propylhexan-1-ol
S.
2,3-Dimethyl-6-(2-methylpropyl)decane
T.
N-Methyl-6-methylheptan-3-amine
U.
3-Ethyl-2,3,6-trimethyloctane
V.
1,4-Dichloro-5-methylheptane
W. 5-(1,1-Dimethylpropyl)nonane
X.
5-(2-Ethylbutyl)-3,3-dimethyldecane
201
Pent-4-en-1-ol
Z.
2-Bromo-3-chlorohept-5-en-1-ol
33. A. 2,2,4-Trimethylpentan-3-ol B.
5-Ethylheptan-2,4-diol
C.
Butane-2,3-diol
D.
Propane-1,2,3-triol
E.
2-Methylphenol
F.
4-Methylphenol
G.
2,5-Dimethylphenol
H. 2,6-Dimethylphenol
I.
1-Methoxy-2-methylpropane J.
K.
1-Phenoxyheptane
L.
Ethoxybenzene
2-Ethoxybutane
M. 2,2,4-Trimethylhexane
N. 2,2-Dimethylbutane
O.
2,5-Dimethylheptane
P.
Q.
3,3-Diethyl-4-methyl-5-propyloctane
R.
3-Methyl-4-propylheptane
S.
5-Ethyl-4,4-dimethyloctane
T.
4-(1-methylethyl)octane
U.
1-Ethyl-2-methylcyclopentane
V.
Ethylcyclobutane
3,3-Diethylhexane
W. 4-Ethyl-1,2-dimethylcyclohexane
X.
3,6-Dimethyldecane
Y.
2-Cyclopropylpentane
Z.
1-Ethyl-3-(2-methylpropyl)cyclohexane
34. A.
4-Methylpentanal
B.
6-chloro-4-ethylhexan-3-one
C.
But-2-enal
D.
Pentan-2,4-dione
E.
3,3,5-Trimethylhexan-2-one
F.
3,3-Dimethylbutanoic acid
G.
Benzene-1,4-dicarbaldehyde
H. 5-Bromo-2-methyloctane
202
2,2,6-Trimethylheptane
J.
2,3,5-Trimethylhexane
K.
3,3-Diethylpentane
L.
5-Methylhexan-3-ol
M. 3-Ethoxyheptane
N. 1-Bromo-4-methylcyclohexane
O.
N,N-Dimethylcyclohexanamine
P.
3-Ethylcyclohexanol
Q.
1,3-Dimethoxypropane
R.
1-Ethoxypropane
S.
4-Methylpentan-1-ol
T.
Butan-2-amine
U.
2-chlorobutane
V.
2-methylpentane
W. 2-Bromo-2-methylbutane
X.
Cyclohexanol
Y.
Z.
Propan-2-amine
35. A.
Propan-2-amine
1 amine
B.
Propan-1-amine
1 amine
C.
N-Methylpropan-2-amine
2 amine
D.
2-Methylpropan-2-amine
1 amine
E.
N-Methylaniline
2 amine
F.
N-Ethyl-N-methylethanamine
3 amine
G.
3-Bromoaniline
1 amine
H. Hexan-1-amine
1 amine
I.
N-propylbutan-1-amine
2 amine
J.
N-(2-methylpropyl)butan-2-amine
2 amine
K.
N,N-Diethylpropan-1-amine
3 amine
L.
Cyclohexanamine
1 amine
Bromocyclopentane
M. 6-Methylheptan-1-amine
1 amine
N. N-Propyl-3-methylbutan-1-amine
2 amine
O.
N,N-Diethylethanamine
3 amine
P.
2,5-Dimethylcyclohexanamine
1 amine
Q.
3-Aminomethylbenzenecarboxylic acid
1 amine
203
3-(Methylamino)benzenecarboxylic acid
2 amine
S.
3-(N-Ethyl-N-methylamino)
benzenecarboxylic acid
3 amine
T.
1 amine
U.
3-Amino-2-ethylbutanoic acid
1 amine
V.
3-Amino-2-ethylbutane nitrile
1 amine
W. 3-Amino-2-ethylbutanal
1 amine
X.
3-Chloropentan-2-amine
1 amine
Y.
2-Aminopentan-3-ol
1 amine
Z.
Methyl-3-amino-2-ethylbutanoate
2 amine
Cl
Cl
36. A.
B.
Br
Cl
C.
E.
D.
Br
Cl
F.
I
Br
G.
H.
I.
J.
K.
L.
204
Br
Br
M.
N.
O.
P.
Q.
OH
OH OH
OH
OH
Ph
OH
R.
OEt
OEt
S.
CH2 OH
U.
T.
V.
OH
NH 2
OH
W.
X.
CH 3
CH 3
OH
Y.
Z.
CH 3
CH 3
O
O
37. A.
B.
O2N
CHO
C.
D.
CH 3
205
E.
Cl
OH
F.
Br O
O
G.
H.
HO
I.
NH 2
J.
Br
K.
M.
NH 2
N.
P.
Q.
R.
S.
T.
U.
V.
Y.
206
Br
N
H
L.
O.
W.
OH
OH
X.
OH
Z.
OH
B.
Cl
D.
E.
NH 2
F.
G.
H.
I.
J.
K.
L.
M.
N.
O.
Q.
Br
Br
Br
P.
R.
OH
S.
Cl
T.
SO 3H
U.
V.
Cl
NO 2
W. Ph
Y.
NH 2
Br
X.
OCH 3
NO 2
CH3
Cl
Z.
Cl
207
B.
C.
NH 2
D.
E.
OH
Br
F.
N
G.
I.
H.
J.
Br
Br
OH
K.
L.
M.
N.
Cl
O.
P.
Cl
OH
CH 3
Q.
R.
Cl
Br
NH2
S.
CHO
NO 2
NO 2
T.
NO 2
208
CH 3
U.
V.
CH 3
W.
Ph
COOH
Y.
40. A.
X.
O
COCH 3
Z.
O
COOH
OCCH 3
COOH
O
4-Methylpent-2-ene
B.
1-Bromo-4-methylhex-3-ene
C.
2,3,4-Trimethylhex-3-ene
D.
1,5-Dimethylcyclohexene
E.
Bromocyclopentane
F.
1-Butoxypropene
G.
3,8-Dibromonon-4-ene
H. 4-Ethyl-3,7-dimethyloct-3-ene
I.
1,5-Dimethylcyclopentene
J.
3-Ethyl-2-methylhept-2-ene
K.
5-Bromopent-2-yne
L.
1-Methoxypent-2-yne
M. 6-Bromo-2-chlorooct-4-yne
N. 3-Ethylhex-1-yne
O.
5-Bromohex-2-yne
P.
5-Methyloct-2-yne
Q.
5,5-Dimethylhex-2-yne
R.
6-Chloro-2-methylhept-3-yne
S.
Cycloocta-1,5-diene
209
1,6-Dimethylcyclohexa-1,3-diene
U.
Hept-1-en-4-yne
V.
But-3-yne-1-ol
W. 4-Methylhexa-1,4-diene
X.
Hepta-1,3,5-triene
Y.
3,5-Dimethylhept-2-ene
Z.
5-Ethenyloct-5-en-1-yne
41. A.
Oct-1-en-6-yne
B.
Hex-3-en-1-ol
C.
Oct-1,5-diyne
D.
Chlorocyclohexane
E.
1-Methylcyclohepta-1,3,5-triene
F.
1-Bromo-1-phenylmethane
G.
1,1-Dibromo-1-phenylmethane
H. 2,6-Dimethylphenol
I.
J.
1-Bromo-2-methylbenzene
K.
1-Ethyl-3-methoxybenzene
L.
M. 2-Chloro-4-ethyl-1-phenylbenzene
N. 4-Nitrophenylethene
O.
1,2,4-Tribromobenzene
P.
1-Cyclohexyl-4-methylbenzene
Q.
3-Chlorobenzenecarbonitrile
R.
Butanenitrile
S.
2-Methylpropylbutanoate
T.
U.
N,N-Dimethylhexanamide
V.
Methylbutanoate
210
Pentanoyl chloride
Y.
Z.
42. A.
5-Ethylheptanoic acid
B.
Pentanoyl chloride
C.
Propylpropanoate
D.
E.
Pentane nitrile
F.
N-Methylbut-3-enamide
G.
Propanoic anhydride
H. 3-Methylpentanoic acid
I.
N,N-Dimethylbutanamide
J.
3-Methylhexanenitrile
K.
3-Methylhexanal
L.
4-Phenylbutanal
M. Heptan-4-one
N. 4-Ethylhexanal
O.
2-Methylheptan-4-one
P.
Hept-1-en-3-one
Q.
6-Hydroxyheptan-3-one
R.
2-oxocyclohexanecarbonitrile
S.
3-Formylpentanamide
T.
4-Bromo-2-chloro-3-cyclopropylcyclohexanol
U.
3-Bromo-2-chloro-5-methylenecyclohexane-1,4-diol
V.
2-Bromo-4-chloro-5-ethynylcyclohexanol
W. 4-Ethynyl-1-methylcyclohexene
X.
3-Bromo-4-chlorooct-3-en-6-yne-2,5-diol
211
4-Chloro-5-(1-methylethenyl)cyclopenta-1,3-diene-1-ol
Z.
5-Prop-2-enylcyclopenta-1,3-diene
43. A.
Octa-1,3,7-triene
B.
Hept-5-en-1-yne
C.
4-Ethenyl-3-ethylhept-6-en-1-yne
D.
Cyclobutylmethylcyclopropanecarboxylate
E.
Prop-2-enyl-3-ethylpent-4-enoate
F.
4-Methylenehexa-1,5-dien-3-one
G.
2-Ethenylbut-3-enal
H. N-Methyl-3-bromobutanamide
I.
N-bromo-3-bromo-4-chlorobut-2-enamide
J.
N-2-Chloro-1-iodoethyl-3-bromo-4-chlorobut-2-enamide
K.
N-Ethyl-N-methyl-3-bromo-4-chloro-2-iodobutanamide
L.
2-Oxobutanal
M. 2-(1-Oxo ethyl)pent-3-enal
N. 5-Chloro-6-cyclopropylhept-3-enoic acid
O.
3,4,5-Triethynyl-6-methyloct-7-ynoic acid
P.
2-Bromo-4-(N-formylamino)-3-methylbutanoic acid
Phenylethyne
T.
U. 2- Amino- 5- hydroxybenzenecarbonitrile
V.
3- Ethenyl-4-formylbenzenecarboxylic acid
W. 4- Methoxycarbonylbenzenecarboxylic acid
X. Phenylbenzene
Y. 4- (2-Bromophenyl)phenol
Z.
212
Methyl-4-formylbenzenecarboxylate
B.
Methyl-4-chlorocarbonylbenzenecarboxylate
C.
Methyl-4-carbamoylbenzenecarboxylate
D.
E.
4-Formyl-2-methyl-3-oxohept-6-ynoic acid
F.
1,4-Bis-(1-methylethyl)benzene
G.
1,4-Bis-(1,1-dimethylethyl)benzene
H. 1,1,1-Trichloro-2,2-bis-(4-chlorophenyl)ethane
I.
3 -B ro m o- 2 , 2 -d i c h l or o- 1 , 1 - bi s- ( 4 - c h l or o -3 methylethylphenyl)benzene
J.
Methyl-2-oxocyclohexanecarboxylate
K.
6-Oxocyclohex-2-enecarboxylic acid
L.
6-Oxocyclohex-3-enecarboxamide
M. 5,6-Dioxocyclohex-2-enecarbaldehyde
N. Cyclohexylbenzenecarboxylate
O.
Phenylcyclohexanecarboxylate
P.
N-Ethyl-N-methylmethanamide
Q.
Methanoyl chloride
R.
Methanamide
S.
Methanal
T.
2-Methylaminocyclohexanone
U.
2-Aminomethylcyclohexanone
V.
2-Hydroxymethylcyclohexanone
W. 2-Hydroxycyclohexanone
X.
6-Hydroxy-2,2-dimethylcyclohexanone
Y.
O,O-Dimethylcyclohex-2-enone
Z.
Phenylmethanoate
213
Exercise
02
Objective Approach
Single Correct Questions (SCQ) :
01. The correct IUPAC name of the alkane
is :-
Cl C C C H is
NO 2 Br F
214
(B)
(C)
(D)
(B)
1
CH
1
2
3
4
5
CH 3 CH = CH CH 2 C
6
CH
7
6
5
4
3
2
1
(C) CH 2 = CH CH = CH CH 2 CH = CH 2
1
2
3
4
5
6 7
(D) CH 2 = CH CH = CH CH 2 C CH
215
correct
IUPAC
C 2 H5
na me
of
the
compound
H2 C = CH CH 2 CH CH 3 is:
(B)
(C)
(D)
CH 2 CH2 CH 3
(D) CH 3 C CH = CH CHO
4
5
3
2
1
CH 3
11. The correct IUPAC na me of the following compound
Cl
I
F
is
Br
(A) 1-Chloro-1-iodo-2-fluoro methyl -4-bromo but-1-ene.
(B) 1-Bromo -4-chloro -3-fluoro methyl -4-iodo but -1-ene.
(C) 4-Bromo -1-fluoro -2-chloro iodo methyl butene
(D) 4-Bromo -1-chloro -2-fluoro methyl -1-iodo but -1-ene.
216
(B)
(C)
(D)
6
5
(C) 4
(B)
6 1
3
2
1
(D)
6 5
1 2
5 4 3
(B)
(C)
(D)
is-
(A) 1-Ethenylcyclopenta-2,4-diene
(B) 5-Ethenylcyclopenta-1,3-diene
(C) Cyclopenta-2,4-dienylethene
(D) Cyclopenta-1,3-dienylethene
217
is:
Cl
(A) 6,6-Dichloroheptan-2-ol
(B) 2,2-Dichloroheptan-6-ol
(C) 6,6-Dichloroheptan-2-al
(D) 6,6-Dichloroheptan-2-one.
SO 3H
NH 2
is
(A) 4-Ethyl-3-methylnonane-2,8-diamine
(B) 6-Ethyl-7-methylnonane-2,8-diamine
(C) 5-Ethyl-1,6,7-trimethylheptane-1,7-diamine
(D) 4-Ethyl-2-methylnonane-2,7-diamine
20. The correct structure of 6-Chloro-4-hydroxycyclohex-2-ene-1sulphonic acid is
(A)
SO 3 H
Cl
SO 3H
(B)
HO
OH
SO 3 H
(C)
Cl
OH
218
Cl
SO 3H
Cl
(D)
HO
Br
COOH
is
(A) 3-Bromobut-2-enoic acid (B) 3-Bromobut-3-enoic acid
(C) 2-Bromobut-1-en-4-oic acid (D) 3-bromo-3-carboxypropene
22. The IUPAC name of the following compound
CH 3 CH = CH CH 2 CH2 CH COOH is
NH 2
(A) 2-Aminohept-5-enoic acid
is
Br
NH 2
(A) 4-Aminomethyl-3-bromocyclohex-5-ene-1-carboxylic acid
(B) 2-Aminomethyl-5-carboxycyclohex-3-en-1-bromine
(C) 4-Aminomethyl-5-bromocyclohex-2-ene-1-carboxylic acid
O is
O
219
is
27. Aspirin is
O
(A)
(C)
O C CH 3
COOH
OH O
C OCH 3
(B)
(D)
O
O C CH 3
COOH
O
O C CH 3
OH
3-Methyl-butanal
2-Methyl-3-butanol
OH CH3
O
2-Methylpentan-3-one
CH3
HO
220
[AIEEE 04]
[AIEEE 06]
Br
(A) 3-Bromo-1-chlorocyclohexene
(B) 1-Bromo-3-chlorocyclohexene
(C) 2-Bromo-6-chlorocyclohex-1-ene
(D) 6-Bromo-2-chlorocyclohexene
31. The IUPAC name of
is
[AIEEE 07]
(A) 3-Ethyl-4,4-dimethylheptane
(B) 1, 1-Diethyl-2, 2-dimethylpentane
(C) 4, 4-Dimethyl-5, 5-diethylpentane
(D) 5, 5-Diethyl-4, 4-dimethylpentane
32. The correct decreasing order of priority for the functional
groups of organic compounds in the IUPAC system of nomenclature is
[AIEEE 08]
(A) -COOH.- SO 3 H,-CONH 2 - CHO
(B) -SO 3 H, -COOH,-CONH 2 , -CHO
(C) -CHO,-COOH,-SO 3H,-CONH2
(D) -CONH 2 - CHO,-SO 3 H,-COOH
33. The IUPAC name of neopentane is :
[AIEEE 09]
(A) 2, 2-Dimethylpropane
(B) 2-Methylpropane
(C) 2,2-Dimethylbutane
(D) 2-Methylbutane
[IIT 06]
221
CN
is
Br
[IIT 09]
(A) 4-Bromo-3-cyanophenol
(B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene
(D) 6-Bromo-3-hydroxybenzonitrile
36. The IUPAC name of CH 3 CH = C CH2 CH3 is:
CH 2 CH 2 CH 3
(A) 3-Propylhex-2-ene
(C) 4-Ethylhex-4-ene
[CPMT 02]
(B) 3-Propylhex-3-ene
(D) 3-Ethylhex-2-ene
CH 3
is :
[AIIMS 03]
(B) 1-Methyl cyclohex-2-ene
(D) 1-Methyl cyclohex-5-ene
[BHU 04]
(B) 3-Methoxy-1-butanol
(C) 1-Methoxy-1-butanol
39. The compound which contains all the four 1, 2, 3 and 4 carbon
atom is:
[CET (J & K) 05]
(A) 2,3-Dimethylpentane
(B) 3-Ethyl-2,3-dimethylpentane
(C) 2,3,4-Trimethylpentane
(D) 3,3-Dimethylpentane
222
(D) 2-Methylpentane
is :
O
(A) 2-Ethyl-3-methyl butanoyl chloride
[AIPMT 06]
is :
223
(A) 1-Hydroxy-4-methylpentan-3-one
(B) 5-Hydroxy-2-methylpentan-3-one
(C) 4-Methyl-3-oxopentan-1-ol
(D) Hexan-1-ol-3-one
47. The correct IUPAC name of the compound
CHO
NO 2
OCH 3
is :
[AFMC 07]
(A) 2-Formyl-5-methoxynitrobenzene
(B) 4-Formyl-3-nitroanisole
(C) 4-Methoxy-2-nitrobenzaldehyde
(D) 4-Methoxy-6-nitrobenzaldehyde
48. The IUPAC name of the compound
H2 C = CH CH CH CH CH3 is:
CH3 C 2 H5 OH
[DPMT 07]
(A) 3-Ethyl-4-methylhex-5-en-2-ol
(B) 3-Methyl-4-ethylhex-1-en-5-ol
(C) 3-Ethyl-2-hydroxy-4-methylhex-5-ene
(D) None of the above
49. How many sigma and pi bonds are there in tetracyano ethylene
molecule?
[BHU (Mains) 08]
(A) 9 and 9
(B) 9 and 7
(C) 5 and 9
(D) 5 and 7
224
[CET 08]
(D) 2-Iodobutane
[AIIMS 08]
O
CN
CH 3
is :
CH 3
[JIPMER (Med.) 08]
(A) Cyclopropionamide
(B) N-Methyl cyclopropanamide.
(C) N,N-Dimethyl cyclopropane carboxamide
(D) None of these
55. The correct IUPAC name of H 2 C = CH - C CH is :[AIPMT 09]
(A) But-3-en-1-yne
(B) But-1-en-3-yne
(C) But-1-yn-3-ene
(D) But-3-yn-1-ene
225
the
following
compound
[AIPMT 10]
(A) Pent-4-yn-2-ene
(B) Pent-2-en-4-yne
(C) Pent-3-en-1-yne
(D) Pent-1-yn-3-ene
OH is
is :
Cl
H3 C
C=C
CH 2 CH 3
I
226
OH O
is :
(A) 2-Hydroxy-4-pentanone
(B) 4-Hydroxy-2-pentanone
(C) 2-Oxo-4-pentanol
(D) 4-keto-2-pentanol
CH3
(B) CH 3 CH 2 C CH 2 CH CH3
Br
CH 3
4-Bromo-2,4-dimethylhexane
(C) CH 3 CH CH CH 2 CH 3
CH3
2-Methyl-3-phenylpentane
CH 3
CH 3
CH CH 2
(B)
[NEET 13]
CH 3 CH CH2 CH 3
CH 3
(D) CH 3 C
CH 3
227
(A)
(B)
Br
Br
(C)
(D)
(B)
CH 3 CCHCH 3
O CH 3
HC CCHCH=CH 2
HC=CH 2
2-Methylbutan-3-one
3-Ethenylpent-1-en-4-yne
OH
CH3
(C)
CH2 CH2 NH2
(D)
228
CH 3 CHCCHOH
CH 3 O CH 3
3-(2-Aminoethyl)-2-methyl
cyclohexan-1-ol
4-Methyl-3-oxopentan-2-ol
(A)
NHCH 2 CH 3
(B)
CH 3 CHCHCHO
Br Cl
3-(N-Ethylamino)-2methylcyclohexan-1-ol
3-Bromo-2-chlorobutanal
CN
(C)
CH 2 CHCH 2 COCl
COOCH 3
(D)
CHO
Methyl 4-chlorocarbonyl
-3-cyanobutanoate
Cyclohexanal
(A)
COCl
(B)
2-Methylcyclo
pentanecarboxamide
Cyclohexanoyl chloride
C N
(C)
2-Methylcyclo
butanecarbonitrite
CH3
Br
(D)
COOCH 3
Methyl 2-bromocyclo
hexanecarboxylate
Iso-propyl
(B)
(C)
Iso-butyl
(D)
Sec-butyl
neo-pentyl
229
(A)
NH 2 2-Chlorocyclohexanecarboxamide
CH 3O
(B)
Cl O
(C)
O O
(D)
H 2-Oxocyclohexane carbaldehyde
230
CH 3
CH 3
is (1-methylethyl) cyclopentane.
H
CN
231
IUPAC
na me
C 2 H 5 CCH2 OH
CH 2
for
the
compound
is 2-ethyl prop-2-en-1-ol.
COOH
OH
Statement-2:When an unbranched carbon chain is directly
linked to more then two like functional groups, then
it is named as derivative of parent alkane which
does not include the C-atoms of the functional
groups.
81. Statement-1:The IUPAC na me of the compound,
OHCCH2 CH 2 COOH is butane-3-formyl-1-oic
acid.
Statement-2:COOH is considered as substituent group while
CHO is considered as the principal functional
group.
82. Statement-1:The IUPAC na me for the compound
C 6 H 5 COOCH 2 CH 2 COOH i s 3 - b e n z o y l o x y
propanoic acid.
232
(A)
Column - II
COOH
CHO
COOH
(B)
CHO
COOH
(C)
(D)
(R) 2-N-Methylaminocyclohexane
carboxylic acid
NH 2
COOH H
N
CH 3
Column - II
Br
(A) Cl
Ph
(B)
CH 3 CHCOOH
COOH
(C)
NH2
(Q)
2,2,3-trifluoro
(R) propanoic acid
2-Bromo-4-chlorocy
(D) CH2 F - CF2 - COOH (S) clohexanecarboxylic acid
233
(B) 18
(C) 12
(D) 9
(B) 2
(C) 4
(D) 5
234
(A) 4-Ethenylhepta-1,3-dien-6-yne
(B) 4-(prop-2-ynyl) hexa-1,3,5-triene
(C) 3-(prop-2-ynly) hexa-1,3,5-triene
(D) 4-Ethenylhexa-4,6-dien-1-yne.
90. IUPAC name of following compound
C OC 2 H5
ethoxy carbonyl
O C CH 3
ethanoyl oxy
235
C NH 2
carbamoyl
C OCH 3
methoxy carbonyl
CH 2 C OH
C Cl
carboxy methyl
chlorocarbonyl
O 6 CO 2 H
1
ClC
(B)
5
2 CO 2 CH3
CN 4 3
O 2 CO 2 H
1
ClC
(C)
3
6 CO 2 CH3
CN 4 5
O 6 CO 2 H
5
ClC
(D)
1
4 CO 2 CH3
CN 2 3
CNHCH 3
236
CO 2 H
(B)
CHBr2
(A)
(B)
CH 3
CH 3
BrCH 2
(C)
CH 2 Br
(D)
CH 3
95. The IUPAC name of C CH 2 OH 4 is
CH 2 Br
237
(a)
N CH 2 - CH 2 - Cl 3
(b)
(c)
CH3 - CH 2 - N - Cl 2
N(CHCH 3 )3
Nitrile
(VI)
Sulphonic acid
(II)
Ketone
(VII)
Ester
(III)
Alcohol
(VIII)
Acid halide
(IV)
Amine
(IX)
COOH
Et
1,1-Dimethyl
Acetone 2-Ethylbutane Pentan-2-oic acid
ethanol
(IV)
II
III
I
CN
CHO
Pentan-2-carbonitrile Pentan-2-al
(V)
(VI)
NC
CN
CN
Propane-1,2,3tricarbonitrile
(VIII)
238
1,6-Dimethyl
cyclohexene
(VII)
HO
OH
OH
Propan-1,2,3-triol
(IX)
Iso-octane
(I)
OH
COOH
COOH
Succinic acid
(III)
COOH
OCOCH 3
Carbolic acid
(IV)
Aspirin
(V)
CH=CHCOOH
Syrene
(VI)
OH
COOH
Cumene
(VII)
Cinnamic acid
(VIII)
Salicylic acid
(IX)
100. How many groups among the following are correctly named.
n-butyl Sec-butyl
(I)
(II)
239
Answers
02
Objective Approach
01.
(B)
02.
(C) 03.
(B)
04.
(B)
05.
(A)
06.
(A) 07.
(D) 08.
(A) 09.
(C) 10.
(D)
11.
(A) 12.
(C) 13.
(B)
14.
(C) 15.
(A)
16.
(B)
17.
(A) 18.
(B)
19.
(A) 20.
(B)
21.
(B)
22.
(A) 23.
(C) 24.
(A) 25.
(D)
26.
(B)
27.
(B)
28.
(C) 29.
(A) 30.
(A)
31.
(A) 32.
(A) 33.
(A) 34.
(D) 35.
(B)
36.
(D) 37.
(A) 38.
(A) 39.
(B)
40.
(D)
41.
(D) 42.
(D) 43.
(B)
44.
(C) 45.
(D)
46.
(B)
47.
(C) 48.
(A) 49.
(A) 50.
(B)
51.
(C) 52.
(B)
53.
(C) 54.
(C) 55.
(B)
56.
(C) 57.
(B)
58.
(B)
59.
(C) 60.
(D)
61.
(A) 62.
(B)
63.
(A) 64.
(A) 65.
(C)
66. (A,B,D) 67. (A,B,D) 68. (A,B,D) 69. (A,B,C,D) 70. (A,C,D)
71.(A,B,C,D) 72.(A,B,C,D)73. (A,C,D) 74. (A,B,C) 75.
(A)
76.
(D) 77.
(A) 78.
(D) 79.
(C) 80.
(A)
81.
(E)
82.
(B)
83.
(C) 84.
(AS ; BP ; CQ ;
DR)
85.
(AS ; BQ ; CP ; DR) 86.
(B)
87.
(B)
88.
(C) 89.
(A) 90.
(B)
91.
(A)
92.
(B)
93.
(B)
94.
(D) 95.
(C) 96.
(A)
97.
(6)
98.
(A) 99.
(4)
100. (6)
101. (12)
102. (6)
240
Test
01
group
which
is
a bsent
in
Penicillin
O
RCN
H
O
S
N
is
COOH
Penicillin
(A) 2 amide
(B) 3 amine
(D) 3 amide
(B)
CH 3 CH COOH
CH 3
(C) CH 3 COOCH 2 CH 3
(D) HCOOH
241
(B) 3
(C) 4
(D) 5
(A) 6, 0, 3, 1
(B) 7, 0, 3, 1
(C) 7, 1, 3, 2
(D) 7, 1, 3, 1
(A) 9, 6, 1
(B) 9, 4, 1
(C) 11, 4, 1
(D) 11, 6, 1
is
(A) C 14 H14
(B) C 14 H10
(C) C 14 H12
(D) C 12 H12
(B) 3
(C) 4
(D) 5
242
6
5
1
4
2
3
(B)
2
1
6 5
(C) 4
6 1
3
(D)
1 2
5 4 3
SO 3H
(A)
SO 3 H
Cl
SO 3H
(B)
HO
OH
SO 3 H
(C)
Cl
OH
Cl
SO 3H
Cl
(D)
HO
SECTION-II
Multiple Correct Questions (MCQ) :
HO
(A) Alcohol
(B) Enol
(C) Ester
(D) Ether
OH
O
OH
HO
Vitamin C
is:
243
(C)
(D)
(B) +N
(C) +N
(D) + S
(A)
and
(B)
(C)
and HC CC CH
(D)
and
H
C=C=C
and
(B)
(C)
(D)
(A) Br
COOH
244
COOH
&
OCOCH3
Br
Br
(B) I
Cl
&
Cl
F
&
(C)
F
(D)
NH2
OH
Cl
&
H2 N
Cl
OH
SECTION-III
Assertion / Reason type Questions (A/R) :
This section has 5 questions. Each question has 5 choice (A),
(B), (C), (D) & (E) out of which ONLY ONE is correct.
(A) Statement-1 is true, Statement-2 is true and statement-2 is
a correct explanation for statement 1.
(B) Statement-1 is true, Statement-2 is true and statement-2 is
not correct explanation for statement 1.
(C) Statement-1 is true and Statement-2 is false.
(D) Statement-1 is false, Statement-2 is true.
(E) Both Statement-1 and Statement-2 is false.
18. Statement-1: Sec-butyl amine is a secondary amine.
Statement-2: In secondary amine, NH2 group attached with
secondary carbon.
245
SECTION-IV
Match the Column type Questions (MTC) :
23. Match the compounds written in Column-I with their name in
Column-II :Column - I
(A)
COOH
CHO
Column - II
(P) 2-(2-Oxoethyl) cyclohexane
carboxylic acid
COOH
(B)
CHO
COOH
(C)
246
NH 2
(R) 2-N-Methylaminocyclohexane
carboxylic acid
CH 3
Column - I
Column - II
(A)
(P) Aliphatic
(B)
(Q) Aromatic
(C)
(R) Alicyclic
(D)
(S) Heterocyclic
(T) Homocyclic
SECTION-V
Comprehension type Questions :
Paragraph for Question Nos. 25-26
A saturated hydrocarbon
(A) has five membered ring. Three alkyl groups attached to the
ring adjacent to each other with following observations.
(A) First group has only two carbon atoms.
(B) Second group has four carbon atom with all hydrogens are
chemically same
(C) Third group has total five carbon atoms and its main chain
contains three carbon atoms with ethyl as a substituents.
25. The IUPAC name of compound (A) is
(A) 2 - ( 1 , 1 - D i m e t h y l e t h y l ) - 1 - ( 1 - e t h y l p r o p y l ) - 3 ethylcyclopentane
(B) 2 - (1 ,1 -Di me th yl eth yl )- 1 -e th yl -3 - (1 -e th ylp ro py l)
cyclopentane
247
(B) 18
(C) 12
(D) 9
(A) 4-Ethenylhepta-1,3-dien-6-yne
(B) 4-(prop-2-ynyl) hexa-1,3,5-triene
(C) 3-(prop-2-ynly) hexa-1,3,5-triene
(D) 4-Ethenylhexa-4,6-dien-1-yne.
28. IUPAC name of following compound
248
(D) 1,1-Diethenylpropyne
SECTION-VI
Integer type Questions :
29. Total number of homocyclic compounds among the given
molecule is
O
O
O
OH
HO
O
OH
is
249
Test
02
O
H3 CCO
OCCH 3
O
(Heroin)
(A) Ester
(B) Ether
(B) 2
(C) 3
(D) 4
250
(B) 2
(C) 3
(D) 4
(A)
(B)
NH
-Lactum
-Lactum
O
NH
(C)
NH
NH
(D)
-Lactum
-Lactum
(Decalin)
(A) 6
(B) 8
(C) 10
(D) 4
R
is
(A) 7
(B) 6
(C) 5
(C) 4
251
OH
(A)
(B)
Menthol
OH
H
Indole
OH
CH 3
(C)
(D)
Phenol
O-Cresol
08. Which among the following is aromatic in nature.
(A)
(B)
(C)
(D)
OH
OH
(C)
(B)
(D)
OH
OH
10. Which among the following will not exist at room temperature.
(A)
(B)
(C)
(D)
SECTION-II
Multiple Correct Questions (MCQ) :
11. Which of the following is/are the homologue of Ethanoic acid
(CH3COOH) .
O
(A)
252
HCOH
(Formic acid)
COOH
(B)
(Butanoic acid)
(C)
COOH
COOH
(Succinic acid)
(D)
(Propanoic acid)
(D)
Cubane
Cumene
13. Which among the following have structure & molecular formula
correctly matched.
(C 6 H 6 )
(A)
(C)
(C 14 H10 )
(C 10 H8 )
(B)
(C 14 H10 )
(D)
14. Which among the following have correct number of substituents present(s).
OH
(A)
OH
Cl O
(3)
(B)
COOH
(C)
Cl
(2)
O
Cl
(D)
(3)
(2)
253
Et
2-Ethylbutane
OH O
(B)
OH
3- Hydroxybutanoic acid
(C)
6 - Methylcyclohex-2-enone
O
CCl
(D)
16. Which among the following structure & their common name
are correctly matched.
OH
O2N
NO 2
O
(A)
(Acetone)
(B)
CH3
NO 2
(Picric acid)
(C)
(D)
HCH
(Formaldehyde)
(Toluene)
17. Which among the following alkyl groups & their name are correctly matched.
(A)
CH 3 CH 2 CH2 CH 2
(n-butyl)
CH 3 CHCH 2 CH 3
(B)
CH 3
(C) CH 3 CHCH 2
(iso-butyl)
254
(sec-butyl)
CH 3
CH3 C
(D)
CH 3
(tert-butyl)
SECTION-III
Assertion / Reason type Questions (A/R) :
This section has 5 questions. Each question has 5 choice (A),
(B), (C), (D) & (E) out of which ONLY ONE is correct.
(A) Statement-1 is true, Statement-2 is true and statement-2 is
a correct explanation for statement 1.
(B) Statement-1 is true, Statement-2 is true and statement-2 is
not correct explanation for statement 1.
(C) Statement-1 is true and Statement-2 is false.
(D) Statement-1 is false, Statement-2 is true.
(E) Both Statement-1 and Statement-2 is false.
OH
18. Statement 1 : Hydroquinone
is alicyclic compound.
OH
Statement 2 : Alicyclic compounds are simply the aliphatic
cyclic compounds.
is aromatic in nature.
255
SECTION-IV
Match the Column type Questions (MTC) :
23. Match the compound given in Column I with their IUPAC
name in Column II.
Column I
O
A.
NH 2
C.
D.
P.
2-N-Methylamino
cyclohexanone
Q.
2-Aminomethyl
cyclohexanone
R.
2-Oxocyclohexane
carboxylic acid
S.
2- Formylcyclohexane
carboxylic acid
H
N
B.
Column II
CH 3
COOH
CHO
COOH
O
24. Match the compound given in Column I with their characteristics in column II.
Column I
A.
B.
C.
256
Column II
P.
Aromatic
Q.
Alicyclic
R.
Anti-aromatic
S.
Homocyclic
T.
Heterocyclic
SECTION-V
Comprehension type Questions :
Paragraph for Question Nos. 25-26
Formaldehyde CH 2 O is known to all biologists because of its
usefulness as a tissue preservative. When pure, formaldehyde
trimerises to give trioxane, C 3 H 6 O 3 , which surprisingly enough,
has no aldehydic or ketonic group. On monobromination reaction trioxane give only one monobromo derivative C 3 H 5 BrO 3 .
25. The structure of formaldehyde is
(A) HOH
H
C=O
(C)
H
(B)
O
HCH
(D) HCOH
O
(A) CH CH CH
3
2
O
(C) O O
(B)
CH 3 CCH 3
(D) O O
O
Paragraph for Question Nos. 27-28
O
Testosterone
257
(B) 6
(C) 7
(D) 8
SECTION-VI
Integer type Questions :
29. Total number of aromatic compounds present in given molecule
are
I
II
III
IV
O
V
VI
VII
VIII
IX
30. Total number of heterocyclic compounds present in given molecules are
N
H
II
O
I
N
III
OH
IV
NH 2
N
HO
258
VI
OCCH 3
COOH
VII
N
H
N
V
O
VIII
S
IX
Test
03
259
(C) Weight
(A) 1, 2
(B) 2, 2
(C) 2, 1
(D) 1, 1
(B)
(C)
(D)
(B) (C 2 H 5 )3 CH
(D) (CH 3 )4 C
(B) 1,1-Dimethylethyl
(C) 2-Methylpropyl
(D) 1-Methylpropyl
Cl
Br
is
260
SECTION-II
Multiple Correct Questions (MCQ) :
11. Neohexane contains
(A) Four 1 carbon atoms and two 2 hydrogen
(B) Twelve 1 hydrogen but no 3 carbon
(C) Two 2 carbon & one 4 carbon
(D) One 4 carbon and two 3 hydrogen
12. The pair of compounds having the same general formula.
H
H
and
and
C C C
(A)
(B)
H
H
(C)
and HC
C C CH (D)
and
261
(A)
(B)
(C)
(D)
H2 C
CH 2
(B)
CH 2
(D)
CH
(C) H2 C
H2 C
CH 2
CH 2
H3 C
CH
CH 2
CH
15. Structure of 2-Ethenyl-3-methylcyclohexa-1,3-diene is/are
(A)
(B)
(C)
(D)
(B)
(D)
262
Methyl 3-ethanoyloxy
propanoate
(A) HO
OMe
(B)
HO
OMe
OMe
O
(C)
COOH
(D)
HO
O
SECTION-III
Assertion / Reason type Questions (A/R) :
This section has 5 questions. Each question has 5 choice (A),
(B), (C), (D) & (E) out of which ONLY ONE is correct.
(A) Statement-1 is true, Statement-2 is true and statement-2 is
a correct explanation for statement 1.
(B) Statement-1 is true, Statement-2 is true and statement-2 is
not correct explanation for statement 1.
(C) Statement-1 is true and Statement-2 is false.
(D) Statement-1 is false, Statement-2 is true.
(E) Both Statement-1 and Statement-2 is false.
18. Statement-1: Neohydrocarbons contain a tertiary carbon atom.
Statement-2: Whenever a carbon atom is bonded to three carbon
atoms it is tertiary.
O
Cl CH 3
C
19. Statement-1:
NH 2 3 - B r o m o - 2 - c h l o r o - 3 Br
methylpentanamide is incorrect IUPAC name.
Statement-2: In case of chain terminating senior most functional
group numbering start from itself.
263
SECTION-IV
Match the Column type Questions (MTC) :
23. Match the compound written in Column-I with its nature written
in Column-II :Column - I
MeOOC
N
O
H
C
3
(A)
Cocaine O
O
CH 3
(P) Carbocyclic
(B)
(Q) Heterocyclic
CH 3
Cis Jasmone of jasmine
O
(C)
CH3
COOH
Column - II
(R) Aromatic
Aspirin
264
(D)
(S) Saturated
HN N
Adenine
(T) Unsaturated
24. Match the compounds written in Column-I with their name in
Column-II :Column - I
Column - II
O
COCHCH3
(A)
CH3
Methyl
(P) cyclopentylethanoate
OH
CH 2 COOCH 3
(B)
Isopropyl 3-hydroxy
(Q) cyclohexaneocarboxylate
O
COOH
(C)
OHC
HOOC
3-Carbamoylcyclobutane
carboxylic acid
(S)
4-Formyl-2-oxocyclohexane
carboxylic acid
O
NH 2
(D)
(R)
SECTION-V
Comprehension type Questions :
Paragraph for Question Nos. 25-26
Have you ever thought that when you read anything from any
book your eyes use an organic compound (retinal) to convert
visible light into nerve impulses. When you pick up this book
from any place, your muscles do chemical reactions on sugars
to give you energy. As you read the words and sentences of this
book, gaps between your brain cells are being bridged by simple
orga nic molecules (neurotransmitter amines) so that nerve
impulse ca n be pa ssed a round your bra in a nd you ca n
265
CH 3H 3 C
O
11-Cis retinal H
(Absorbs light when we see)
(B) 7
(C) 8
(D) 5
(B) 3, 5, 4
(C) 3, 6, 3
(D) 4, 6, 2
266
SECTION-VI
Integer type Questions :
29. How many of the compounds among these are unsaturated in
nature.
SH O
SH
O
H3 C
O
H 3C
CH 3
CH3
CH3
SH
Olean sex pheromone
Compound with
Compound with
of olive fly
worst smell
worst smell
(III)
II
I
O
H
CH 3
N
N
CH 3
N
O
O
HO
Compound from
Paracetamole
Nicotine
cakes & biscuits
(V)
(VI)
(IV)
O
HN
H H
CH 3
S
R
N
NH
O
CH
N
O
3
Indigo dye
COOH
O
(VIII)
Penicilin
Cl O
(VII) O
NH
S NH 2
O
OH
Furosemide (Sulpha drug)
(IX)
30. How many of the compound among these have all atoms sp2
hybridized which form the ring.
N
(I)
N
H
(II)
O
(III)
N
H
H
H
(V) (VI) (VII) (VIII)
(IX)
S
(IV)
267
Answers
Test 01
1.
6.
11.
16.
21.
24.
27.
(B)
2. (C)
3. (C)
4. (B)
5. (C)
(B)
7. (C)
8. (B)
9. (B)
10. (B)
(A,B,C,) 12. (A,C,D) 13. (B,C,D) 14. (C,D) 15.(A,B,C,D)
(C,D)
17. (B,C,D) 18. (E)
19. (D)
20. (B)
(C)
22. (A)
23. (A-S ; B-P ; C-Q ; D-R)
(AQ,T ; BP,R,T ; CP ; DQ,S)
25. (B)
26. (B)
(A)
28. (B)
29. (6)
30. (4)
Test 02
1.
6.
11.
16.
21.
24.
27.
(D)
2. (C)
3. (D)
4. (A)
5.
(C)
7. (B)
8. (C)
9. (B)
10.
(A,B,D) 12. (A,B,D) 13. (A,B,C,D) 14. (A,B,C,D) 15.
(A,B,C,D) 17. ()
18. (D)
19. (A)
20.
(E)
22. (A)
23. (AQ ; BP ; CS ; DR)
(AP,S ; BP,T ; CR,S ; DQ,S)
25. (B)
26.
(B)
28. (B)
29. (5)
30. (6)
(B)
(A)
(B,C,D)
(A)
(C)
Test 03
1. (C)
2.
6. (C)
7.
11. (A,B)
12.
16. (A,B,C,D) 17.
21. (B)
22.
DQ,R,T)
24.
27. (C)
28.
(D)
3. (A)
4. (C)
5. (D)
(D)
8. (B)
9. (C)
10. (A)
(C,D)
13. (A,B,C,D) 14. (A,B)
15. (B,D)
(A,C)
18. (D)
19. (D)
20. (B)
(B)
23. (AQ,R,T ; BP,T ; CP,R,T ;
(AQ ; BP ; CS ; DR) 25. (B)
26. (D)
(C)
29. (7)
30. (7)
268