Question Details

Predict the major product ‘P’ in the following sequence of reactions-


Options

A

B

C

D

Show Answer

Correct Answer :

Option D

Option 4

Solution :

The correct option is the fourth option (Option 4), which represents 1-methyl-2-(aminomethyl)cyclopentane (or (2-methylcyclopentyl)methanamine).

Let us break down the reaction sequence step-by-step to understand how the major product ��P’ is formed:

Step 1: Anti-Markovnikov addition of HBr (Kharasch effect)
When 1-methylcyclopentene (a cyclopentene ring with a methyl substituent on one of the double-bonded carbons, C1) is treated with hydrogen bromide (HBr) in the presence of benzoyl peroxide, the reaction proceeds via a free-radical chain mechanism:
1. The peroxide initiator decomposes to form free radicals, which react with HBr to generate a bromine radical:
Br
2. The bromine radical attacks the alkene double bond. It selectively adds to the less-substituted carbon (C2) to form a more stable tertiary radical at the C1 position (bearing the methyl group) rather than a secondary radical.
3. The tertiary radical then abstracts a hydrogen atom from a molecule of HBr, yielding the anti-Markovnikov product:
1-bromo-2-methylcyclopentane

Step 2: Nucleophilic Substitution (SN2 reaction)
When 1-bromo-2-methylcyclopentane is reacted with potassium cyanide (KCN):
The cyanide ion (CN-) acts as a nucleophile and undergoes nucleophilic substitution, replacing the bromide ion (Br-) at the secondary carbon (C2). This yields:
1-cyano-2-methylcyclopentane (2-methylcyclopentanecarbonitrile)

Step 3: Mendius Reduction of the Nitrile
Treating the nitrile with sodium amalgam in ethanol (Na(Hg)/C2H5OH) reduces the nitrile group (-CN) to a primary amine group (-CH2NH2):
This Mendius reduction converts 1-cyano-2-methylcyclopentane into:
1-methyl-2-(aminomethyl)cyclopentane (also named (2-methylcyclopentyl)methanamine), where the methyl group (-CH3) and the aminomethyl group (-CH2NH2) are located on adjacent carbons of the cyclopentane ring.

This structure corresponds directly to the one shown in Option 4 (Image 4).

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