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Dehydration of Alcohols

A,B and C are...

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(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. HCI give the same product (D).

(a) Write the structures of (A),(B),(C) and (B).

(b) Out of (A), (B) and (C) isomers, which one is least reactive towards addition of HCN?

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Solution

(a) Molecular formula of carbonyl compound = $C_{4} H_{8} O$

A, B, C are three non-cyclic functional isomer of $C_{4} H_{8} O$ .

A and C give Tollen's test but B does not give it but gives iodoform test. Hence,

A and C are aldehydes and B is a Ketone.

A and B on reduction with Zn/Hg and $O H^{-}$ gives D. So,

A = $C H_{3} - C H_{2} - C H_{2} - C H O$

B = $C H_{3} - C O - C H_{2} - C H_{3}$

C = $(C H_{3})_{2} - C H - C H O$

D = $C H_{3} - C H_{2} - C H_{2} - C H_{3}$

(b) B is least reactive towards addition of HCN.

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Q. (A),(B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular formula

C_{4} H_{8} O .

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(a) Write the structures of (A),(B),(C) and (B).

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