Question

A halide with formula C₆H₁₃Br gave two isomeric alkenes A and B on dehydrobromination. On ozonolysis of mixture of A and B the following compounds were obtained: CH₃COCH₃, CH₃CHO, CH₃CH₂CHO and (CH₃)₂CHCHO. The halide is:

• A. 2-Bromohexane
• B. 3-Bromo-2-methylpentane
• C. 1-Bromo-2,3-dimethylbutane
• D. 2-Bromo-3,3-dimethylbutane

Hint:

Use ozonolysis product analysis to trace back the structure of alkene and identify its parent halide.

Answer 1

The Correct Option is B

The given ozonolysis products suggest the formation of multiple alkenes which can be formed from elimination of HBr from 3-Bromo-2-methylpentane. The various products account for both symmetrical and asymmetrical cleavage of double bonds.