Q19 / 69 · JEE Advanced 2011 (Paper 1) · Chemistry

The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic $\mathrm{KOH}$ is

Correct answer: 5

Solution

The substrate has three different types of $\mathrm{B}-\mathrm{H}$, therefore, first, three structural isomers of alkenes are expected as Figure
The last two alkenes II and III are also capable of showing geometrical isomerism hence two geometrical isomers for each of them will be counted giving a total of five isomers.

Hence, the correct answer is 5.

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