CHAPTER TEST 5. You have two C 6H10O ketones, I and II.

Both are
CH3CO3H
1. O Product of the reaction is optically active, but I is racemised by treatment with
base and II is not. Wolff-Kischner reduction of both
ketones gives the same achiral hydrocarbon, formula
O C 6H12 . What reasonable structures may be assigned
to I and II ?
(a) O O (b) O
O (a) I is 3-methyl-4-penten-2-one; II is
4-methyl-1-penten-3-one
O (b) I is 2-methylcyclopentanone; II is 3-methyl-
cyclopentanone
(c) I is 3-methylcyclopentanone; II is 2-methyl-
(c) O O (d) cyclopentanone
(d) I is 2-ethylcyclobutanone; II is 3-ethyl-cyclobutanone
HO OH
6. Treatment of A(C 5H12O) with concentrated sulphuric
2. Which carbon-carbon bond could not be formed by acid results in the formation of three alkenes in
an aldol condensation reaction ? differing yields. Also, A forms a yellow precipitate on
(b) (a) treatment with NaOH/I2. A turn colour of acidified
dichromate solution to blue green, forming a new
(d)
HO O organic compound B which also forms yellow
(c) precipitate on treatment with NaOH/I2. The most likely
name of A is/are
OH (a) 3-methyl-2-butanol (b) 3-methylbutanol
O
(c) 2-pentanol (d) either “b” or “c”.
3. Arrange the followings in the increasing order of 7. The carbonyl compound(s) that will undergo
reactivity towards aldol condensation reaction racemisation on treatment with aqueous KOH is/are
O CH3
O
(i) O2N
CH3 (a)
Ph
O O
(ii)
(b)
CH3

O CH3
(iii) MeO CH3
O
CH3

O (c)
(iv) H3C
CH3 O
(a) (i) < (ii) < (iii) < (iv)
(d)
(b) (iv) < (iii) < (ii) < (i) H
(c) (iii) < (ii) < (iv) < (i)
(d) (iii) < (iv) < (ii) < (i) CH3

4. Compound A(C 7 H13Br) is a tertiary bromide. On 8. Which of the following reactions has/have equilibrium
treatment with sodium ethoxide in ethanol, A is constant (KC ) greater than one?
converted to a hydrocarbon B. Ozonolysis of B
followed up by work up with Zn ¾ H 2O gives (a) CH3CHO + KOH l
6-oxoheptanal as the only product. The most likely
CH2CH — OK + H2O
structure of A is
Br
(a) (b) O O
Br + KOH l
(b)
H H
Br Br O OK
(c) (d) + H2 O
H H
 Assertion-Reason Type
Following two questions have assertion followed by the
(c) O + KOH l reason. Answer them according to the following options.
(a) Both assertion and reason are correct and reason is the
correct explanation of the assertion.
OK + H2O (b) Both assertion and reason are correct but reason is not the
correct explanation of assertion.
(c) Assertion is correct but reason is incorrect.
(d) Assertion is incorrect but reason is correct.
O O 11. Assertion When pure d-(+)-2-methylbutanal is treated
(d) + KOH l with dilute H 2SO 4 , it is racemised completely.
H2N NH2
Reason It’s a-carbon is chiral which undergo keto-enol
tautomerism in the presence of acid catalyst.
O OK
+ H2 O 12. Assertion When benzaldehyde (C 6H 5CHO) is treated
H 2N NH2 with concentrated NaOD solution in D2O, Cannizzaro
reaction occur but no C—D (bonds with deuterium) is
formed.
Passage for Q. Nos. 9 and 10 Reason Cannizzaro reaction involves hydride transfer
mechanism.
Consider the following reaction to answer the next three
questions : 13. Match the carbonyls from left Column with their
O characteristics from right Column :
(i) O3 KOH
C10H14(A) B Reaction type Halides
(ii) (CH3)2S heat
O O p. Gives just one aldol only

9. The most likely structure of A is

A. CH3
(a) (b)
O q.
Gives yellow precipitate
with I 2/NaOH
B. H 3C CH3

(c) (d) O r. Produces isomeric oximes

with HONH 2
C.
CH3CH2 CH2CH3

10. If B is heated with Zn(Hg) in concentrated HCl solution, the O s. Gains more than 4 u in
product formed is molar mass on treatment
(a) Decane with NaOD/D 2O
D.

(b) O
t. Gives more than one aldol

14. If ethanedial (HOC—COH) is treated with excess of

(c) HCN(aq) followed by hydrolysis of product results in
diacids. How many different diacids would be formed ?

(d) 15. If CH 2D ¾ CHO is treated with dilute alkaline solution,

how many different aldols (excluding stereoisomers) are
expected ?

Answers
1. (b) 2. (a) 3. (d) 4. (b) 5. (b) 6. (a, c) 7. (b, d) 8. (b, c) 9. (c) 10. (a)
11. (a) 12. (a) 13. A ® q,r,t; B ® p,q,s; C ® p; D® r,s,t 14. (3) 15. (4)