(A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular formula C 4H 8O . Isomers (A) and (C) give positive Tollen’s test whereas isomer (B) does not give Tollen’s 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?
(a) Compound A and C give tollen’s test which indicates that they are aldehydes. Compound C gives iodoform test which means it contains a carbonyl carbon so, with formula C4H80 the structure of the compound would be CH3COCH2CH3 .Now upon reduction with Zn/Hg conc. HCl, the corresponding alkanes are obtained, so reduction of B gives Butane (D, so the isomer A have to be linear chain aldehyde, giving Butane on reduction. So the last isomer possible is compound C, 2-Methyl propanal. As shown below
A is CH3 CH2 CH2CHO
B is 
C is 
(b) will be least reactive as the carbonyl carbon is sterically hindered and most reactive would be compound A towards the addition of HCN.
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