Question Details

Major products A and B formed in the following , are

Options

A

                                                                                                                                  .

B

                                                                                                                                .

C

                                                                                                                                .

D

                                                                                                                                .

Show Answer

Correct Answer :

Option A

                                                                                                                                  .

A = 1-bromo-2-methylcyclohexane; B = 1-methylcyclohexene

Solution :

The given reaction sequence starts with 2-methylcyclohexanol:

Step 1: Formation of Product A
When 2-methylcyclohexanol is treated with phosphorus tribromide (PBr3), a nucleophilic substitution reaction occurs. The hydroxyl group (-OH) on the cyclohexane ring is replaced by a bromine atom (-Br).
Thus, the major product A is 1-bromo-2-methylcyclohexane:
2-methylcyclohexanol+PBr3→1-bromo-2-methylcyclohexane (A)

Step 2: Formation of Product B
When 1-bromo-2-methylcyclohexane (Product A) is treated with alcoholic KOH under heating (alc. KOH / Δ), it undergoes dehydrohalogenation via an E2 elimination mechanism.
The base abstracts a proton (H+) from one of the adjacent β-carbons relative to the carbon bearing the bromine atom:
1. Abstraction of a proton from the tertiary β-carbon (C2, which holds the methyl group) yields a trisubstituted alkene, 1-methylcyclohexene.
2. Abstraction of a proton from the secondary β-carbon (C6) yields a disubstituted alkene, 3-methylcyclohexene.
According to Zaitsev's rule, the elimination reaction preferentially forms the more highly substituted, more stable alkene as the major product. Since a trisubstituted alkene is more stable than a disubstituted alkene, 1-methylcyclohexene is the major product.
Thus, the major product B is 1-methylcyclohexene.

Therefore, the structures corresponding to A and B are:
A = 1-bromo-2-methylcyclohexane
B = 1-methylcyclohexene

Unlock Our Free Library

Access expert-curated educational resources and study materials—completely free.

Ask AI Tutor
5 left
Q1 View Question & Options
AI Tutor is solving this question...
Reading question context & options...