Alcohols and Ethers - Result Question 56
####61. An alcohol $A$, when heated with conc. $H _2 SO _4$ gives an alkene $B$. When $B$ is bubbled through bromine water and the product obtained is dehydrohalogenated with excess of sodamide, a new compound $C$ is obtained. The compound $C$ gives $D$ when treated with warm dilute $H _2 SO _4$ in presence of $HgSO _4$. $D$ can also be obtained either by oxidising $A$ with $KMnO _4$ or from acetic acid through its calcium salt. Identify $A, B, C$ and $D$.
$(1983,4 M)$
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Solution:
- $\left(CH _3 COO\right) _2 Ca \xrightarrow{\Delta} CH _3-\underset{D}{\stackrel{|}{C}}-CH _3+CaCO _3$
$$ X \underset{H _2 O}{\stackrel{NaNH _2}{\longrightarrow}} CH _3-\underset{C}{C} \equiv CH $$
