Hydrocarbons - Result Question 58
####43. The major compound $Y$ is (a)
(c)
(b)
(d)
Passage 2
An acyclic hydrocarbon $P$, having molecular formula $C _6 H _{10}$, gave acetone as the only organic product through the following sequence of reactions, in which $Q$ is an intermediate organic compound.
$$ \underset{\left(C _6 H _{10}\right)}{P} \xrightarrow[\substack{\text { (ii) } NaBH _4 / \text { ethanol } \ \text { (iii) dil. acid }}]{\text { (i) dil. } H _2 SO _4 / HgSO _4} $$
(2011)
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Answer:
Correct Answer: 43. (a)
Solution:
Passage 2
The final ozonolysis product indicates that the alkene before ozonolysis is
Also $P\left(C _6 H _{10}\right)$ has two degree of unsaturation and oxymercuration demercuration hydration indicates that it is an alkyne. As alkyne, on hydration, gives a carbonyl compound which on reduction with $NaBH _4$ gives a $2^{\circ}$ alcohol.
$-C \equiv C-+H _2 O \longrightarrow \stackrel{\stackrel{O}{C}-CH _2-}{\text { (i) } NaBH _4} \underset{\text { (ii) } H^{+}}{\underset{H}{C}-\left.\right| _{2^{\circ} \text { alcohol }} ^{OH}-CH _2-}$
The secondary alcohol that can give above shown alkene on acid catalysed dehydration is
