Hydrocarbons - Result Question 59
Passage
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)
44. The structure of the compound $Q$ is
Show Answer
Answer:
Correct Answer: 44. (b)
Solution:
- The final ozonolysis product indicates that the alkene before ozonolysis is
Also $P\left(\mathrm{C}6 \mathrm{H}{10}\right)$ 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 $\mathrm{NaBH}_4$ gives a $2^{\circ}$ alcohol.
The secondary alcohol that can give above shown alkene on acid catalysed dehydration is
BETA
