Carboxylic Acids and their Derivatives - Result Question 55
####41. A hydrocarbon $A$ of the formula $C _8 H _{10}$, on ozonolysis gives compound $B\left(C _4 H _6 O _2\right)$ only. The compound $B$ can also be obtained from the alkyl bromide $C\left(C _3 H _5 Br\right)$ upon treatment with magnesium in dry ether, followed by carbon dioxide and acidification. Identify $A, B$ and $C$ and also give equations for the reactions.
(1996, 3M)
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Solution:
- $B$ is $C _3 H _5 COOH$ and $A$ is $C _3 H _5-C \equiv C-C _3 H _5$
Also $A$ on ozonolysis gives $B$ indicates that there is no olefinic bond in $C _3 H _5$-unit of $A$ and it is cyclopropyl group.
$$ \begin{array}{ll} \Rightarrow & A=\Longrightarrow C=C-\square \ & B=\Longrightarrow COOH \ \text { and } & C=\Longrightarrow Br \end{array} $$
