ISOMERISM

1. Select the correct statement :

(i) Isopentane and neo-pentane are chain isomers
(ii) 1-Methoxy propane and 2-methoxy propane are position isomers
(iii) CH 3  CH 2  S  CH 2  CH 3 and CH 3  S  CH 2  CH 2  CH 3 are metamers

(iv) N an N CH3 are functional isomers (v) and are ring-chain isomers
CH3 H

(vi) C 7 H 8O can form 4 structural isomers

O OH
|| |
(vii) CH 3  C  CH 3 and CH 3  C  CH 2 are canonical structures

Me Et
(viii) an are chain isomers (ix) Et N and Et N are related as metamers
Pr Et

(x) C3H 6 O 2 can show functional and metamerism

2. How many compounds are capable to show tautomerism.

O O O O
|| || || || Me
(i) Ph - CH 2  C  Ph (ii) CH 3  C  CD 3 (iii) HCCC Me
Me
O H
O
CH3 N O
(iv) (v) (vi)
O

O
NH

(vii) (viii) NO2 (ix)

O O

O O O

(x) (xi) (xii)

N O
H

3. Some pairs are given in which case enol will be more stable :
O O O O
|| || || ||
(i) CH 3  C  CH 3 , CD 3  C  CD 3 (ii) ,
CH 3  CH 2  C  CH 3 CH  C  CH
3 3
 O O O O
|| || || ||
(iii) CH 3  C  CH 2  C  O  CH 3 , CH 3  C  CH 2  C  CH 3

O O O O
|| || || ||
(iv) CH 3  C  CH 2  C  CH 3 , CH 3  C  CH 2  C  C 6 H 5

O O O O
|| || || ||
(v) CH 3  C  O  CH 2  CH 2  C  CH 3 , CH 3  C  O  CH 2  CH 2  C  C 2 H 5

NH O +
O OH
NH
(vi) , (vii) , , (viii) ,
NH NH O O O

O O
|| ||
(ix) CH 3  C  NH 2 , CH 3  C  NH  CH 3 ,
Cl
(x) Cl + SbCl5  Product , + SbCl5  Product
O O
O O
|| ||
(xi) CH 2  CH  CH  CH  CH 2  C  H, CH 2  CH  CH  CH  CH 2  C  CH 3

(xii) ,
O

O O O O
|| || || ||
(xiii) CH 3  C  CH 2  C  O  C 2 H 5 (CCl4), CH 3  C  CH 2  C  O C 2 H 5 (CH3Cl)

NH 2 NH 2 NH
NH || ||
(xiv) | || ,
CH 3  C  CH  CH  CH 3 (H 2 ) CH 3  C  CH  CH  CH 3 (HCl)

4. How many compounds will show geometrical isomerism

CH3 C=C CD3 CH2-Cl

(i) CHD = C (ii) (iii) C=C
CH2CH3 CH 3 CH 3
Me

D D CH3
CH3 CH = CH2 CH3
(iv) C=C (v) (vi) H
D CH2-CH=CH2
H T H
 d d Ph
(vii) (viii) (ix) C=C (x)
Me
C=N
l l
OH
(xi) CH3-N=N-CH3 (xii) H N=N CH3
CH3 CH3
Me H
(xiii) C=C H (xiv)
Me C=C
H D
CH3 CH3

5. Arrange the given compounds as instructed :

CH3 C 2H 5 CH 3 CH2Cl
(i) C=C , C=C (Boiling point)
CD3 C 2H 5 C 2H 5 CH 2Br
CH 3 CH 3 CH 3 C 2H 5
(ii) C=C , C=C (Melting point)
C 2H 5 C 2H 5 C 2H 5 CH3
CH 3 CH 2COOH H COOH
(iii) C=C , C=C (Anhydride formation)
C2 H 5 COOH HOOC H

CH3 CH2-COOH CH 3 OH
(iv) C=C , C=C (Acidic Nature)
C 2H 5 CH3 CD3 CH 3

6. How many compounds can show optical isomerism :

35
CH3
Cl
C2H5 H CH2 CH = CH2
(i) CH3 C Br (ii) (iii)
C
Cl
37
CH3 CH = CH CH3

O
H CH2 C CH3 H CH 2 CH 2 OH
(iv) C (v) C O CH2 CH 3
CH3 CH2 C = CH2 CH3
OH
CH3 Cl Cl
(vi) CH2 = C = C (vii) Br C C Br
C Br I I
I
Cl
Me Me
H
(viii) C CH2 (ix) C C C (x)
D C C C

NO2 NO2
Me Me

(xi) C C C (xii)
Et Et
C2H5 C2H5
 F Br Cl CH2

R1 R1 R1 R1
(xiii) (xiv)
R2 R2 R2 R2

Cl

7. Write all the standard confermers, also find most and least stable conformers.
(i) Cl  CH 2  CH 2  OD (ii) Br2  CH 2  CH 2  Cl 2
(iii) D  CH 2  CH 2  D (iv) F  CH 2  CH 2  Cl

8. Find the relation between (i) and (ii)

CH=CH2 D Cl Cl
(i) D CH3 , C2H5 CH=CH2 (ii) H Br , Br H

C2H5 CH3 I I

CH3 CH3
H OH HO H Br Br
(iii) , (iv) ,
Br H H Br Br Br
CH3 CH3

ANSWER KEY
----------------------------------------------------------------------------------------------------
1. (i) Ans : T (ii) Ans : F (iii) Ans : T (iv) Ans : T
(v) Ans : F (vi) Ans : F (vii) Ans : F (viii) Ans : F
(ix) Ans : T (x) Ans : T

2. Ans : (i, ii, iv, v, vi, vii, viii, ix, x, xi, xii)

3. Ans : (i-a, ii-b, iii-b, iv-b, v-a, vi-a, vii-b, viii-b, ix-a, x-a, xi-a, xii-a, xiii-a, xiv-a)

4. Ans : (i, iii, iv, v, vi, vii, ix, x, xi, xii, xiii, xiv)

5. Ans : (i–Second, ii–Second, iii–First, iv–First)

6. Ans : (i, ii, iii, iv, v, vi, vii, x, xi, xii, xiii, xiv)

8. Ans : (i) R,S (ii) R,S (iii) d,l (iv) Identical