Question

A halide with formula $C_6{H}_{13}Br$ gave two isomeric alkenes $\left(A\right)$ and $\left(B\right)$ with formula $C_6{H}_{12}$. On reductive ozonolysis of a mixture of $\left(A\right)$ and $\left(B\right)$, the following compounds were obtained: ${CH}_{3}CO{CH}_3,{CH}_{3}CHO,{CH}_3{CH}_{2}CHO$ and ${\left({CH}_3\right)}_{2}CHCHO$. The halide is:

• A. 2-Bromohexane
• B. 3-Bromo-2-methylpentane
• C. 2,2-Dimethyl-1-bromohexane
• D. Unpredictable

Answer 1

The correct option is B 3-Bromo-2-methylpentane

Alkene has six C atoms. Combine two products of ozonolysis containing three C atoms each.
Combine two products of oznolysis containing four C and two C atoms to get another alkene.
Alkene $\left(A\right)$ and $\left(B\right)\underset{Alc.}{\overset{KOH}{\leftarrow }}$ 3-Bromo-2-methyl pentane,

Option B is correct.