CBSE Class 12 Chemistry 2018 Solved Paper

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Question : 18
Total: 26
(A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular formula C4H8O. Isomers (A) and (C) give positive Tollens' test whereas isomer (B) does not give Tollens' test but gives positive Iodoform test. Isomers (A) and (B) on reduction with Zn(Hg) conc. HCl give the same product (D).
(a) Write the structures of (A), (B), (C) and (D).
(b) Out of (A), (B) and (C) isomers, which one is least reactive towards addition of HCN ?
Solution:  
(b) (B) as ketones are less reactive towards addition of HCN than aldehydes and alkane due to higher hinderance caused by steric effect and inductive effect.

(c) The possible non-cyclic functional isomers of a carbonyl compound having molecular formula.

C4H8O are
CH3CH2
(I)
CH2
CHO

CH3
O
C
(II)
CH2
CH3


CH
CH
|
CH3
CHO
(III)

Since isomer (B) does not give Tollen's test, it must be a ketone but it gives positive iodofo on test, so it must be methyl ketone. Hence, structure of (B) is (II).
The isomers (A) and (C) give positive Tollen's test so both the isomers are aldehyder. Since isomers (A) and (B) on reduction with ZnHg / conc. HCl give the some product (D).
CH3
O
C
CH2
CH3
(B)
Zn(Hg)
conc. HCl
CH3CH2CH2CH3
(D)

Structure of (A) is (I) and Structure of (C) is (III).
Hence,
ACH3CH2CH2CHO
BCH3C
O
O
CH
2
CH3

CCH3
CH
|
CH3
CHO

DCH3CH2CH2CH3
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