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Nomenclature
Nomenclature
CHEMISTRY
ALLEN
Study Package
For – JEE (Advanced)
JEE-Chemistry
EXERCISE-01 CHECK YOUR GRASP
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. IUPAC name of the hydrocarbon (A) is :
CH3
A:
C2H5
(A) 2-ethyl-5methylhexane (B) 5-ethyl-2methylhexane
(C) 2, 5-dimethylheptane (D) 5-ethyl-2,5-dimethylpentane
2. IUPAC name of neopentyl group is :
(A) 2,2-dimethylbutyl (B) 2, 2-dimethylpropyl (C) 1, 1-dimethylbutyl (D) 1, 1-dimethylpropyl
3. IUPAC name of the following compouund is :
OH
CH3
O O O
(A) (B) (C) (D) none of these
OH OH OH
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OH
CH3
(A) –CH3 < –OH < C=C (first) (B) –OH<–CH 3 < C=C (first)
(C) C=C<–CH 3 <–OH (first) (D) –CH3 < C=C < – OH (first)
7. C 4 H 8 O 2 represents :-
(A) An acid only (B) An ester only
(C) An ketone only (D) An acid and an ester also
8. The higher homologue of dimethylamine (CH 3 —NH—CH 3 ) has the structure :-
(A) (CH 3 ) 3 N (B) CH 3 —CH 2 —CH 2 —NH 2
NH2
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NH2
CH3 CH2
(a) (b) (c) (d)
Correct code is :
(A) only a and b (B) a, b and d (C) a, c and d (D) All of them
12. Common name of CH 2 CH—CN is :-
(a) acrylonitrile (b) vinyl cyanide
(c) allyl cyanide (d) allyl nitrile
(A) a, b and d (B) a and b (C) only b (D) a, b and c
13. Which of the following names is correct :-
(A) 4–Isopropyl–3–methyl hexane (B) 2–Ethyl–3–isopropyl pentane
(C) 3–Isopropyl–4–methyl hexane (D) 3–Ethyl–2,4–dimethyl hexane
14. The correct systematic IUPAC name of the given compound is :
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H
18. The correct name for C O is :-
OH
(A) 2–Hydroxy cyclopentanal (B) 2–Formyl–1–hydroxy cyclopentane
(C) 2–Hydroxy cyclopentane carbaldehyde (D) Cyclopentane–2–ol–1–al
CH2 CH2
19. The name for the structure H2C CH C Cl
CH2 CH2
O
(A) Cyclo hexanoyl chloride (B) Cyclohexane carbonyl chloride
(C) 1–Chloro cyclohexanal (D) Chloro cyclohexyl methanal
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Cl
CH3
3. has the IUPAC name as :-
C2H5
(A) 3–Chloro–1–ethyl–2–methylcyclopentane (B) 1–Chloro–3–ethyl–2–methylcyclopentane
(C) 4–Chloro–1–ethyl–5–methylcyclopentane (D) None of above
4. The IUPAC name of CH 3 CH 2 NHCHO is :
(A) N–formyl ethanamine (B) Ethyl amino methanal
(C) N–ethyl methanamide (D) None of them
Me
COOC2H5
HO
7. has the IUPAC name :-
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CH3
N N–Methyl-N-Ethylethanamine
(C) Et (D)
3-Ethyl-7-iodobicyclo (2.2.1) heptane
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)
O
14. The compound CH3—CH2—C—CH2 may be named as :
CH3
CH2 — CH — CH2
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CH(OH)COOH
CH(OH)COOH
(A) tartaric acid (B) 2,3-dihydroxy butane-1,4-dioic acid
(C) '-dihydroxy succinic acid (D) None of these
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Column-I Column-II
(A) Wood spirit (p) 2-Butyne
(B) Acetone (q) Trichloromethane
(C) Dimethyl acetylene (r) Methanol
(D) Chloroform (s) Propanone
Column-I Column-II
(A) C n H 2n + 2 (p) Alkynes
(B) C n H 2n (q) Alkenes
(C) C n H 2n – 2 (r) Cyclohexane
(D) C 6H 12 (s) Paraffins or alkanes
3. Match column I with column II and select the correct answer from the given codes :
Column-I Column-II
(compounds) (number of carbons in the bridges)
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2 . NC—CH2—CH—CH2—CN 3-cyanopentane-1,5-dinitrile
CH2COOH
3 . HOOC—CH2—CH—CH2—COOH 3-(carboxymethyl)-1,5-dioic acid
CH2CHO
4 . OHC—CH2—CH—CH2—CHO 3-(formylmethyl)pentane-1,5-dial
Comprehension # 2
In addition to the standard ring systems (such as cyclohexane), cyclic compounds can also be bicyclic,
tricyclic, etc. or they can be spirocyclic, bicyclic or bridge head carbons. The point of attachment of two
rings are called bridge head atoms.
The formal names of bicyclic and related ring systems are based on
(a) Total numbe of atoms in the molecule.
(b) The number of atoms in each bridge connecting the bridge head atoms. These numbers are written in
square bracket in decreasing order.
Spirocyclic compounds have two fused rings, but only one bridge head atom. Spirocyclic compounds are
named like bicyclic compounds, but have the prefix spirocyclo. Answer the following question :
1.
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CH2—CH2 CH2—CH
(A) (B) (C) (D) CH2
CH2—CH2 CH2—CH
Comprehension # 3
Branched- chain alkanes are named according to the following rules.
(1) Longest chain Rule - Locate the longest continuous chain of carbon atoms. This chain determines the
parent name of the alkane.
(2) Lowest set of locants - The longest continuous chain are numbered by arabic numerals 1, 2, 3, 4, ....
from one end of chain to the other, in such a manner that carbon atom carrying first substituent gets the
lowest number.
(3) Name of the branched chain alkane - The substituent name and the parent alkane are joined in one word
and there is a hyphen between the number and the substituent name.
(4) Alphabetical order of the side chains - When two or more substituents are present, give each substituent
a number corresponding to its position on the longest chain, the substituent group should be listed
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alphabetically.
(5) Numbering of different alkyl groups at equivalent positions- If two different alkyl groups are present at
equivalent positions the numbering of the parent chain is done in such a way that alkyl group which
comes first in the alphabetical order gets the lower number.
(6) Naming of same alkyl groups at different positions - When two or more substituents are identical,
indicate this by the use of prefixes di, tri, tetra and soon. Commas are used to separate numbers from
each other.
(7) Rule for larger number of substituents - If a compound has two or more chains of the same length, the
parent hydrocarbon is the chain with the greater number of substituents.
(8) Numbering the complex substituent - Name such as iso-propyl, sec-butyl and tert-butyl are acceptable
substituent name in the IUPAC system of nomenclature but systematic name are preferable. Systematic
substituent names are obtained by numbering the substituent starting at the carbon that is attached to the
parent hydrocarbon. This means that the carbon that is attached to the parent hydrocarbon is always the
number –1carbon of the substituent.
CH3 CH3
CH3CH3
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CH3—CH2—CH—CH—CH—CH2—CH3
CH3 CH2—CH3
(A) 5-Ethyl-3-Methyl-4-(1-Methylpropyl) octane (B) 4-Ethyl-6-Methyl-5-(1-Methylpropyl) octane
(C) 3-Ethyl-5-Methyl-4-(1-Methylpropyl) octane (D) 4-Sec-butyl-5-Ethyl-5-Methylheptane
3. The correct IUPAC name of the following compound is -
CH3—CH2—CH2—CH—CH2—CH2—CH—CH3
CH—CH3 CH3
CH3
(A) 2-Methyl-5-isopropyloctane (B) 2, 6-Dimethyl-5-propylheptane
(C) 5-isopropyl-2-Methyloctane (D) 4-(1-Methylethyl)-7-methyloctane
4. The molecular weight of following compound is 3, 7 - Diethyl -2, 2-dimethyl-4-propylnonane :-
(A) 230 (B) 236 (C) 254 (D) 240
5. The correct IUPAC name of following compound is -
CH3
CH3—C—CH2—CH2—CH—CH2—CH2—CH2—CH3
CH3 CH3—C—CH3
CH3—CH—CH3
(A) 2, 3, 3, 7, 7 Pentamethyl-4-butyloctane
(B) 4-Butyl-2, 3, 3, 7, 7 pentamethylnonane
(C) 2, 2-Dimethyl-5-(1', 1', 2'-trimethylpropyl)nonane
Matc h th e C o lu m n
1. A - (r), B - (s), C - (p), D - (q)
2. A - (s), B - (q, r), C - (p), D - (q, r)
3. A - (q), B - (r), C - (s), D - (p)
C o mp rehe ns i o n B as ed Q u e st i o ns
C omp rehensi on # 1 : 1. T 2. F 3. F 4. T 5. T
C o mp rehe nsi on # 2 : 1. (C) 2. (B) 3. (B) 4. (A)
C o mp rehe nsi on # 3 : 1. (A) 2. (C) 3. (A) 4. (C) 5. (C)
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1. A cartain substances contains only carbon and hydrogen and has a molecular weight of 70. Photochemical
chlorination gave only one monochloride. Write the structure and IUPAC name of the hydrocarbon and
its monochloride.
2. A hydrocarbon of molecular weight 72 g mol –1 has a 2-methyl group. What is the IUPAC name ? Also
drawn its bond-line structure ?
3. Write the structure and give IUPAC systematic name of an alkane or cycloalkane with the formula :
(a) C8H 18 that has only primary hydrogen atoms
(b) C6H 12 that has only secondary hydrogen atoms.
4. What is wrong with the names given for these compounds provide the correct name for each :
(i) (ii)
2-ethyl-2-pentene
3-cyclohexylpropane
(iii) (iv)
1, 3, 4-trimethylcyclo-pentane 2, 2-methylbutylcyclopentanol
CH3 CH3 CN
O O O CH3
OH
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CH3
(i) H3C —N—C—CH2—CH3 (ii) CH 2(COOH) 2 (iii) CH3—CH=C—CH2—COOH
CONH2
CH3C2H5
CH3
1. and —Cl 2. CH3—CH—CH2—CH3
CH3CH2CH2
CH3
8. (i) (ii) (iii)
CH3 CH2CH3
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5. Which one of the following does not have sp hybridised carbon ? [AIEEE -2004]
(1) Acetone (2) Acetic acid
(3) Acetonitrile (4) Acetamide
Cl
[AIEEE-2006]
Br
(1) 6-bromo-2-chlorocyclohexene
(2) 3-bromo-1-chlorocyclohexene
(3) 1-bromo-3-chlorocyclohexene
(4) 2-bromo-6-chlorocyclohex-1-en
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CH3
CH3–CH2C=CH–CHCH2CH3
CH3CH2–CH–CH2CH2CH2CH3
(A) 5,6–diethyl–8–methyl dec–6–ene (B) 5,6–diethyl–3–methyl dec–4–ene
(C) 6–butyl–5–ethyl–3–methyl oct–4–ene (D) 2,4,5–triethyl–3–ene
3. The IUPAC name of - [IIT-91]
OHCCH=CH–CH–CH=CH2
is -
CH2CH2CH2CH3
CH2–CH3
5. A compound with molecular formula C 8 H 14 , contains 12 secondar y and two ter tiar y H atoms. The
compound is : [IIT-93]
O
6. IUPAC name of C6H5 – C – Cl [IIT-06]
1. B 2. B 3. B 4. B 5. B,C,D 6. B
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