Question 14 Marks

An organic compound (A) [Molecular formula $\left.C _8 H _{10} O _2\right]$ was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives but-1-ene.
Write equations for the reactions involved.

Answer

Dehydration of (C) gives but-1-ene which have four carbon atoms so other product (B) also have four carbon and this will have terminal - COOH . So compound (A), $( B ),( C )$ are as follows :
(A) $CH _3- CH _2- CH _2- COOCH _2- CH _2- CH _2- CH _3$ Butyl butanoate (ester)
(B) $CH _3- CH _2- CH _2- COOH$ (Butanoic acid)
(C) $CH _3- CH _2- CH _2- CH _2- OH$ (Butan-1-ol)
Equations of the reactions are as follows :

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