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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 C 4 H 8 O . 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 ofHCN ?
(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
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.
C 4 H 8 O are −
− CH 2 − CHO
CH 3 −
− CH 2 − CH 3
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 withZn ∕ Hg / conc. HCl give the some product (D).
∴ Structure of ( A ) is ( I ) and Structure of (C) is (III).
Hence,
A ⇒ CH 3 − CH 2 − CH 2 − CHO
B ⇒ CH 3 − C −
− CH 2 − CH 3
C ⇒ CH 3 −
− CHO
D ⇒ CH 3 − CH 2 − CH 2 − CH 3
(c) The possible non-cyclic functional isomers of a carbonyl compound having molecular formula.
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
Hence,
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