CHAPTER TEST 1.

Arrange the following in the increasing order of their Br

Br
heat of hydrogenation (-DH ).
(c) (d)

(I)
5. Which of the following can not be obtained as the only
product in the Wurtz’s coupling reaction of halides
with sodium metal in ether solution?
(II)
(a) (b)

(III) (c) (d)

6. Which of the following is not a spontaneous reaction,

i.e. has equilibrium constant(K) less than one?
(IV)
(a) CH 3 ¾ C ºº CH + CH 3Li S
(a) I<II<III<IV (b) IV<III<II<I CH 3 ¾ C ºº CLi + CH 3
(c) IV<III<I<II (d) I<II<IV<III
(b) CH 3 ¾ C ºº CH+CH 3CH 2ONa S
2. Which radical is responsible for the observed
selectivity in the chain reaction below? CH 3 ¾ C ºº CNa + C 2H 5OH

Cl (c) CH 3COOH+CH 3 ¾ C ºº CNa S

Cl–Br
+ CH 3COONa +CH 3 ¾ C ºº CH
hv
(d) CH 3CH == CH 2+CH 3 ¾ C ºº CNa S
CH 3CH == CHNa +CH 3 ¾ C ºº CH
Cl
2% 98%
(a) Cl (b) Br Passage for Q. Nos. 7 to 9
(c) H (d) 2° radical Consider the following scheme of synthesis of a chloro
pyridine to answer the next three questions
3. Which of the following products is formed when
1,2,4-trimethylcyclopentene is hydrogenated? Cl
Cl
X (CH3)3COK
(CH3)3COH
N N
(I) (II) ½ ½
H H
Y
Cl
Cl
– Cl–
Chloro pyridine
Z
N
(III) (IV)

7. The reagent X is
(a) CH 2N 2/heat (b) CH 2Cl 2/NaOH
(a) Only I (b) I and III (c) CHCl 3/KOH (d) CH 2 l 2
(c) Only II (d) II and IV
8. The final product Z is
4. Taking into account the stability of various cycloalkens Cl
and carbocation as well as the rules governing
(a) (b)
mechanism of the carbocation rearrangement. What is
most likely of the reaction? N Cl N
Cl
+ H—Br ?
(c) (d)
Br Br
N N
(a) (b)
Cl
9. The compound Y can also be converted into Z using a Lewis 10. Assertion During addition of Br2 to propene, following
acid catalyst AlCl 3 . The reactive intermediate involved now is reactive intermediates are formed :
Å Cl Cl +
(a) (b) Br Br
Å ½ + |
N N H 3C ¾ CH ¾ C H 2 S H 3C ¾ CH ¾ CH 2
½ ½ (I) (II )
H H
Å Cl Cl Reason I and II are resonance structures.
Cl Cl
(c) (d)
11. Assertion Ozonolysis of 3-hexyne followed by hydrolysis
N N gives propanoic acid.
½ Reason The by product H 2O 2 oxidises ozonide to acid.
H
12. How many different isomers (including stereoisomers) of
Assertion-Reason Type (Q.No. 10-11) a monocarboxylic acid with molecular formula C 6H12O 2 ,
Following two questions have assertion followed by the reason. on decarboxylation with soda lime will produce the same
Answer them according to the following options.
n-pentane?
(a) Both assertion and reason are correct and reason is the correct
explanation of the assertion. 13. 4-bromo-2-pentene has a chiral carbon and can show
(b) Both assertion and reason are correct but reason is not the enantiomerism. If a racemic mixture of
correct explanation of assertion.
4-bromo-trans-2-pentene is treated with Br2 in CCl 4 in
(c) Assertion is correct but reason is incorrect.
the presence of FeBr3 , 2,3,4-tribromopentane is
(d) Assertion is incorrect but reason is correct.
formed. How many stereoisomers would be produced
in this reaction?

Answers
1. (a) 2. (b) 3. (b) 4. (b) 5. (a,d) 6. (b,d) 7. (c) 8. (d) 9. (a) 10. (b)

11. (a) 12. (4) 13. (3)