ORGANIC CHEMISTRY (ISOMERISM)

BYVINEET KHATRI SIR

EXPERT BATCH DPP

1. Identify the relation between P and Q

COOH
COOH
P Q
(a) Position Isomers (b) Metamers (c) Chain Isomers (d) Tautomers

2. The minimum number of carbon atoms required to show chain isomerism in simple alkanes is :
(a) 5 (b) 4 (c) 3 (d) 2

3. Which type of isomerism cannot be shown by a compound of molecular formula C20H42O?

(a) Functional Isomerism (b) Metamerism
(c) Ring chain isomerism (d) Chain Isomerism

4. Which of the following option shows the correct relationship between the compounds?

(a) ; (Positional isomers)

O O
(b) ; (Functional isomers)
O O

H3C – CH2

CH – CH3 H3C – CH – CH – CH2 – CH3

(c) CH3– CH2– CH CH2 CH3 ; (Identical)

CH3 CH3

O
(d) ; (Chain isomers)
O

5. Which one of the following compound is optically inactive?

Cl
(a) CH3–CH=CH–CHDCl (b) F Me
D
CH3
H H
(c) C=C=C (d) F Me
F F
Cl
6. Which of the following structure(s) represent 2-bromo-3-chloropentane?
CH3 Cl
Br
H H Me
Br Me H Et
, , ,
Cl Br H Cl H H Et H

Cl Br
1 2 3 4

(a) 1, 2, 3, 4 (b) 2, 3, 4 (c) 2, 4 (d) 3, 4

7. Chiral form of cyclohexane is :

(a) Chair (b) Half chair
(c) Twist boat (d) Boat

8. Which structure is possible for molecule formula C9H7O2Cl ?

O O O
O OH O O Cl
H H Cl

Cl Cl
O Cl O Cl
1 2 3 4 5

(a) 1, 2, 3, 4, 5 (b) 1, 4, 5 (c) 3, 4, 5 (d) 1, 3, 4, 5

9. Which molecule is optically inactive ?
O
(a) (b) CH3–CH=C=CH–CH3
O
OH
(c) (d)
CH3 COOH

10. Select the correct combination of optical rotation of compounds along with their relative configuration

CHO CHOH
CHO
H OH C=O
H OH HO H
HO H
H OH
H OH
CH2OH H OH
H OH
Glyceraldehyde CH2OH
CH2OH
(I) Glucose
Fructose
(II) (III)

I II III
(a) (+) ; (D) (+) ; (D) (+) ; (D)
(b) (+) ; (D) (+) ; (D) (–) ; (D)
(c) (–) ; (L) (+) ; (D) (–) ; (L)
(d) (+) ; (D) (–) ; (L) (+) ; (D)
11. Which molecule is not chiral.
Cl

CMe3
(a) C=C=C=C=C (b) Me CH – COOH
MeC3

Cl

Ph Ph

(c) (d) N N
O O

C = CH – C – OH

12. Which compound has centre of symmetry in any of the conformation?

CH3
CH3
H OH Br H
H Cl Br

(a) Cl H
(b) H OH (c) (d)
Br H Br
CH3
CH3

13. Most stable form of meso-2,3-butanediol is:

Me Me Me Me
H Me HO H HO Me Me H
(a) H OH (b) H OH
(c) H OH
(d) H OH
OH Me H OH

14. Which of the following is not a pair of diastereomers?

COOH COOH
H Cl H Cl

and
(a)
Cl H H Cl
COOH COOH

Me Me
H CH 3 CH3 H
and
(b) CH3 H CH3 H
Me Me

(c) and

Me
Me Me
H OH
(d) and
H OH
H OH Me H OH
15. Most stable conformation of n-Pentane is (Consider C2 – C3 bond rotation):
Et H CH3 Et
H H H Me H H H H

(a) (b) (c) (d)

H H Et H H Et H H
Pr H H Et

CH3 CH3
O O
16. CH3–CH–C–O and CH3–CH2–CH2– C–O are related as :
CH3 CH3
CH3

(a) Metamer (b) Geometrical isomer

(c) Position isomer (d) Chain isomer

17. Which of the following isomeric structure has the lowest energy?

(a) (b)

(c) (d)

18. Determine the order of enolic content

(I) (II)
O O

(III) (IV)

(a) II > III > IV > I (b) I > III > IV > II (c) I > IV > III > II (d) IV > III > I > II

19. Which of the following compound has aromatic character in enol form?

O O
O O
(a) (b) (c) (d)
NH
O O
20. Which One of the following is not a pair of functional isomers?
O
(a) and OH
O O
(b) C—O—H and H—C—O—

O
H
(c) and
O

O OH
(d)
and

21. Which of the following compound will show tautomerism?

O O

(a) (b) Me3C – C  N (c) (d)

O
N–OH CH3 CH3

22. How many geometrical isomers are possible for

H3C – CH = CH – CH = CH – CH = C = C = CH – CH3
(a) 32 (b) 4 (c) 8 (d) 6

O
C–O &
23. O–CH=O have the relation :

(a) Positional isomer (b) Functional group isomer

(c) Metamer (d) Chain isomer

Sol. C–O & O–CH=O are Metamer..

24. Butyric acid and -methyl propionic acid are :

(a) Positional isomers (b) Chain isomers (c) Metamers (d) Tautomers
 O
||
25. Me  O  C  Me and Et–O–CH=O are
(a) Functional isomers (b) Metamers
(c) Positional isomers (d) Chain isomers

26. Which of the following are position isomers?

(a) &

(b) &

OH
(c) & OH

(d) COOH
&
COOH

27. Which of following will exhibit geometrical isomerism?

(a) 1-phenyl-2-butene (b) 3-phenyl-1-butene
(c) 2-phenyl-1-butene (d) 1,1-diphenyl-1-propene

28. and CH3 are pair of

H3C CH2–CH=CH2 H CH=CH–CH3

(a) Geometrical isomer (b) Ring chain isomer

(c) Position isomer (d) Chain isomer

29. Which of the following species is aromatic?

O O

(a) Tautomer of (b) Tautomer of

O
O

(c) Tautomer of (d) Tautomer of

30. Which structure may have meso form as a stereoisomer?
(a) 2,3 dimethyl butane (b) 2-butanol
(c) 1-ethyl 3-methyl cyclohexane (d) 2,3,4-trichloro pentane

31. How many conformers of 1, 2-dichloroethane contain atleast one P.O.S?

(a) 4 (b) 1 (c) 2 (d) 3

32. How many geometrical isomers are possible for given isomer “A” ?

A

Cl

(a) 4 (b) 2 (c) 3 (d) 1H

33. Which of the following can show both optical isomerism as well as geometrical isomerism?
H3C–H2C
OH H3C CH3
(a) (b) C=C=C
H CH3 H H

Br H H

(c) (d)
H Cl CH

34. Indicate the incorrect statement regarding given compound.

Br CH3
H

H Br
CH3
(a) Compound does not have plane of symmetry.
(b) Compound does not have centre of symmetry.
(c) Compound is chiral in nature.
(d) Compound does not have C2-axis of symmetry.

35. How many fractions are obtained on fractional distillation of products in following reaction?
CH3
Cl Dichloro Products (Including stereoisomers)
H Cl
h
CH
HC
3 CH
(S)-2-Chloro-3-methylbutane

(a) 3 (b) 4 (c) 5 (d) 6

36. How many diastereomers are possible for D(–)-fructose ?
CH2–OH
C=O
HO H
H OH
H OH
CH2–OH
D(–)–Fructose

(a) 4 (b) 5 (c) 6 (d) 7

37. Which option is correct by matched ?

O O
(a) HO C–O & C–O OH Metamers

(b) NH & Functional group isomers

NH2

(c) & Ring chain isomers

(d) & Chain isomers

38. Which of the following is incorrectly matched with its number of stereoisomers?
Cl
(a) , 3 (b) H3C – CH = CH – CH3 , 2
Cl

(c) , 2 (d) ,8

39. Which of the statement is correct ?

CH3 CH2CH3
H3C H H H
&
(a) are conformational isomers
H CH3 H3C H
CH2CH3 CH2CH3

O OH
(b) are tautomer
&
COCl

(c) & are chain isomers

COCl
(d) Z-2-Bromobut-2-ene & trans-2-Bromobut-2-ene are geometrical isomers.
40. Which of the following will show optical as well as geometrical isomerism ?

COOH Ph Cl
Cl Cl

H
(a) Ph H HOOC (b) (c) (d) None of these
Cl Cl
Cl
H H

41. Correct statement about D-mannitol (in given form):

OH OH
HO
OH
OH OH
(a) C3 axis of symmetry (b) C2 axis of symmetry
(c) Centre of symmetry is present (d) 3-chiral centre are present

42. Which of the following structure cannot show optical isomerism?

O
(a) (b)
O

(c) (d)

43. Reaction :–1 CH3–CH2–CH2–CH2–CH3 Cl


2 Optically active monochloro product(s)
h
are (R)

Cl
Reaction :–2 
2 Optically active di-chloro product(s) are (S)
h

Cl
Reaction :–3 
2 Optically active di-chloro product(s) are (P)
h

Reaction :–4 2-methoxy propane Cl


2 Optically active mono chloro product(s)
h
are (Q)
Sum of P + Q + R + S is
(a) 8 (b) 9 (c) 10 (d) 11

44. Identify total number of geometrical isomers in given compound?

H Me

H2N–N N–NH2
(a) 2 (b) 4 (c) 6 (d) 8
 H Cl
Cl H Br
Cl
45. (I) (II) (III)
Br H H
Br
H H

H Cl H H
H H H H

(IV) (V)
H H H Cl
H Br H Br
Which statement is incorrect?
(a) I and II are geometrical isomers
(b) II and IV are conformers
(c) I and III are identical compounds
(d) III and V are trans conformers
O
OD/D2O
46. Deuterated carbonyl compound (J)
long time

'J' is :
O
O
D
D D
(a) (b) D
D
D3C
D D

O O
D D D D
(c) D (d) D
D3C D3C
D D

47. How many monobromoderivatives are possible for ?

(a) 11 (b) 13 (c) 14 (d) 15

48. The number of aromatic structural isomer possible for C6H3BrClI are ?
(a) 10 (b) 8 (c) 12 (d) 6
49. Which of the following isomeric relationship is correctly matched?

(a) ; (Positional isomers)

O
O
(b) O ; (Functional isomers)
O

H3C–CH2
CH–CH3
(c) CH3–CH2–CH H3C–CH – CH–CH2–CH3 ; (Homomers)
CH3 CH2 CH3
CH3

O
(d) ; (Chain isomers)
O

50. How many different constitutional isomers of molecular formula C7H16 are possible, which contains five
carbon Parent Chain?
(a) 4 (b) 5 (c) 6 (d) 7
 ANSWER AND SOLUTION
1. (c)

Sol. COOH
COOH
2-Methylbutanoic acid Pentanoic acid
Difference in length of the parent chain : Chain isomers.

2. (b)
Sol. Minimum number of carbon atoms required to show Chain isomerism is 4.

Butane 2-Methylpropane

3. (c*)
Sol. DBE of the given compound = O : Ring cannot be formed by this compound.

4. (c)
Sol. (a) Compounds are identical : Nona-1,4,8-triene
(b) Compounds are metamers. Functional group is same (ester) so, not functional isomers.
(c) Both are identical compounds : 3,4-Dimethylhexane
(d) Both compounds have the same parent chain, so not chain isomers.

5. (d)
CH3
Sol. F Me It does not contain chiral carbon as two same methyl groups are present.
Cl

6. (a)
Sol. All compounds are 2-Bromo-3-cloropentane
5
Br CH3 Cl
1 45 2
3
H H Me
Br Me H Et 1 2
1
2 2
3 4 3 4 3
5 , , ,
1 54
Cl Br H Cl H H Et H
Cl Br
1 2 3 4

7. (c)

Sol.
Pos = no
Cos = no
Active = yes
Chiral = yes
8. (d)
Sol. DBE of molecule formula C9H7O2Cl = 6

O O O
O OH O O Cl
H Cl
H

Cl Cl Cl OH
O O
DBE = 6 DBE = 5 DBE = 6 DBE = 6 DBE = 6

9. (d)
Sol. (d) contains plane of symmetry.

POS

10. (b)

CHO CHO CHOH

2

H OH H OH C=O
HO H
Sol. HO H
CHOH H OH H OH
H OH
(+) D-Glyceraldehyde H OH
CHOH
CHOH
(+) D-Glucose (–)–D–Fructose

11. (d)
Sol. (d) contains a plane of symmetry.
Ph Ph
+ +
N N
¯ O O¯

12. (b)
CH3
H
H OH H OH
OH
Sol. (b) H C.O.S.
OH
CH3CH3 CH3

13. (a)
Sol. a is most stable due to intramolecular H-bonding
c & d are not meso.
14. (b)

COOH
H Cl COOH
Cl H
Sol. (a)  Cl H
Cl H COOH
COOH
Diastereomers
COOH
H Cl COOH
 H Cl
Cl H
H Cl
COOH COOH

(b) Chiral carbon is not present

(c) and Geometrical isomers are diastereomers.

Me Me
Me H OH Me
H OH
  HO H
H OH Me HO H
H OH Me
(d) Diastereomers
Me Me
Me Me
Me HO H
  HO H
H OH H OH
H OH H OH Me

15. (b)
Sol. The staggered form is most stable due to least strain.

16. (d)
Sol. Since the two differ in principle carbon chain they are chain isomers (Structural isomers) and structural
isomers can not be stereoisomers

17. (d)
Sol. In (d) both the bulky methyl groups are at equatorial position, thus it is the most stable.

18. (c)
Sol. I has ~ 100% end due to dipole-dipole repulsion in the diketo form.
IV has ~ 0% enol as it can over come dipole-dipole repulsion by rotation.

19. (c)
O OH
O
Sol. (a) does not tautomerize (b) l

O Non Aromatic
 O OH OH

O
(c) l (d) l N
 NH
O OH 4e Anti-aromatic
10e Aromatic

20. (d)
Sol. (a)  F.G..I. (Ether and Alcohol) (b)  F.G.I. (Acid and Ester)
(c)  F.G..I. (Ketone and Aldehyde) (d)  Tautomers (Keto and Enol form)

21. (a)

O OH

Sol. can show tautomerism

N–OH N=O

22. (c)
Sol. Compound : H3C – CH = CH – CH = CH – CH = C = C = CH – CH3 shows GI about the circled bonds.

Total G.I. = 23 = 8 Ans.

23. (c)

Sol. C–O & O–CH=O are Metamer..

24. (b)
COOH
Sol. : Chain isomers
COOH

25. (b)
Sol. CH 3  C  OCH 3 H  C  O  CH 2  CH 3
|| ||
O O
Methyl ethanoate and ethyl methanoate have different alkyl groups attached to divalent functional group
i.e. ester, so they are metamers
26. (c)
Sol. (a) Chain isomers
(b) Not isomers
(c) Position isomers
(d) Chain isomers

27. (a)
Sol. CH3 – CH = CH – CH2 – Ph will show geometrical isomerism.

28. (c)

Sol. CH3

3 2 1 2 1
H3C CH2–CH=CH2 H CH=CH–CH3
3
The position of double bond is different so they are position isomers.

29. (a)
O OH

Sol. (a) (Aromatic)

O OH

(b) (Non Aromatic)

O OH
(c)  (Anti Aromatic)

O
OH
(d)   (Non Aromatic)

30. (d)
Sol. (a) CH 3  CH  CH  CH 3 Optically inactive because no chiral carbon.
| |
CH 3 CH 3

(b) CH 3  CH  CH 2  CH 3 Optically active as it has only one chiral carbon.

|
OH
Et

(c) Optically active as it has no symmetry

Me
 (d) CH 3  CH  CH  CH  CH 3 It has a plane of symmetry, hence it can have meso form.
| | |
Cl Cl Cl

31. (c)
Sol. There are two conformers containing
Cl
Cl Cl
H H
H
H H H H
H
Cl
POS = 1 POS = 2

32. (a)
Sol. Number of systems showing geometrical isomerism (n) = 2. Total geometrical isomers = 2n = 22 = 4

33. (d)
H3C–H2C Br H
OH C CH3
* C=C=C
H CH3 H H
Sol. H Cl
Optical iso. = yes Optical iso. = yes
geometical iso. = no Optical iso. = no
geometical iso. = no geometical iso. = yes

H
*
(cis)
* CH3
Optical iso. = yes
geometical iso. = yes

34. (d)
C2-AOS (at z-axis)
CH3 POS = no
H Br
COS = no
Sol. Active (chiral) = yes
H Br AOS = yes
CH3

35. (c)
CH2–Cl CH3 CH3 CH3

Sol. H Cl + Cl Cl + H Cl + H Cl

(2) CH CH (1) C Cl CH*

H3C CH3 H3C CH3 H3C CH3 H3C CH2–Cl
(Total 5 fractions obtained) 2 diastereomers
(S, R), (S, S)
36. (c)
Sol. D i a s t e r e o m e r s o f g i v e n - o p t i c a l l y a c t i v e i s o m e r = ( T o t a l O . I – 2 ) = ( 2
3 –2) = 6

37. (b)
Sol. Primary amine & secondary amine are functional isomers

38. (c)
Sol. (c) has total 3 stereoisomers as its trans form is optically active.

39. (c)
1
COCl
3 4
2 & 2
Sol. 4 5 3 chain isomers
COCl
1

40. (d)
Sol. (a)  Plane of symmetry / centre of symmetry in all stereoisomers
(b)  Plane of symmetry / centre of symmetry
(c)  Plane of symmetry in all stereoisomers.
Hence none of the compounds can show optical isomerism. Also only (b) can not show geometrical
isomerism.

41. (b)

OH OH
HO
Sol. OH
OH OH
C2 axis of symmetry

42. (d)

Sol. (d) has plane of symmetry and thus won’t shown optical isomerism P.O.S.

43. (b)

H
|
Sol. Reaction 1: CH3–CH2–CH2–CH2–CH3 Cl
2 CH 3 *C CH 2  CH 2  CH 3

h
|
Cl
P = 2 optically active monochloro product

Cl
Reaction 2: 
2 , ,
h
 Q = 3-optically active dichloro products

Cl
Reaction 3: 
2
h

R = 2-optically active dichloro products.

H H
| |
Reaction 4: CH 3  C  CH 3 Cl

 2 CH 
*
C  CH2Cl
3
| h |
OMe OMe
S = 2 optically active monochloro products
P+Q+R+S=9 Ans.

44. (b)
H y
x N–NH2
Sol. C z
Me N–NH2
There will be four geometrical isomers possible ,of the given compound.
x y z
– E E
– Z Z
E E Z
Z E Z
45. (d)
Cl Cl
Sol. and (V) are enantiomers.
Br Br

46. (c)
Sol. Thus H atoms are replaced which are attached with carbon where negative charge appears & negative
charge appears on that carbon which can be stabilised by –M of  C 
||
O

47. (c)
Br

2
Sol. h monobromination
Total of 14 isomers are formed including stereoisomers.
48. (a)
Sol. Possible structures are
Cl Cl Cl Cl Cl
Br Br Br I Br I

I I Br
I
Cl Cl Cl Cl Cl
I I

Br I Br Br I
I Br Br

6 4 4 6
7 3 3 7
5 5
49. (a) 8 2 2 8 Both compounds have same IUPAC names
9 1 1 9

O
2
1
O 1
(b) 2 O 3 Both Functional group are esters (Compounds are metamers)
O

1 2
H3C–CH2
3
CH–CH3
4 5 6
(c) CH3–CH2–CH4
6 5
H3C–CH – CH–CH2–CH3
3

CH3 2 CH2 CH3

1
CH3

Both are 3, 4-dimethyl hexane. Thus, identical

2 4
O 3
4
(d) 1 5 (Positional isomers)
2
1
3 5 O

50. (b)

2 4 4 4
3 2 3 2 3 2 3 4
Sol. 1 5 1 5 1 5 1 5

1
2
2 4 3 5
3 (Six carbon parent chain)
1 5 6
4