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Question

Identify the product Z in the following series of reactions:

A
Hexanoic acid
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B
α-methyl caproic acid
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C
Heptanoic acid
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D
None of these
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Solution

The correct option is C Heptanoic acid
We know that glucose is an aldohexose. Glucose reacts with HCN to give a cynohydrin at the aldehyde group (X). When this cyanohydrin is hydrolysed, we get an acid at the nitrile position(Y). When this is reduced by using HI/heat, we get heptanoic acid.
CHO(CHOH)4CH2OH+HCNCH(CN)OH(CHOH)4CH2OH (cyanohydrinX)

CH(CN)OH(CHOH)4CH2OH+H2OCOOH(CHOH)5CH2OH(Y)

COOH(CHOH)5CH2OH+HICOOH(CH2)5CH3 (heptanoicacidZ)

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