Question Details

Predict the major product 'P' in the following sequence of reactions:


Options

A

.

B

.

C

.

D

.

Show Answer

Correct Answer :

Option A

.

Option 1

Solution :

The correct option is Option 1 (which corresponds to the structure 1-methyl-2-(aminomethyl)cyclopentane as shown in image_1.webp).


Here is the detailed step-by-step chemical pathway to determine the major product P:


Step 1: Anti-Markovnikov addition of HBr (Hydrobromination in the presence of peroxide)
The starting material shown in image_0.webp is 1-methylcyclopentene.
When it is treated with hydrogen bromide (HBr) in the presence of benzoyl peroxide, the reaction proceeds via a free-radical mechanism. This leads to the anti-Markovnikov addition of HBr across the double bond.
The bromine atom (Br) selectively adds to the less substituted carbon atom of the double bond (C2), while the hydrogen atom adds to the more substituted carbon atom (C1, which bears the methyl group).
This yields 1-bromo-2-methylcyclopentane as the intermediate product.


Step 2: Nucleophilic Substitution with Potassium Cyanide (KCN)
Next, the intermediate 1-bromo-2-methylcyclopentane is reacted with potassium cyanide (KCN).
The nucleophilic cyanide ion (CN-) attacks the secondary carbon bearing the bromine atom, displacing the bromide leaving group via an SN2 mechanism.
This substitution reaction yields 1-cyano-2-methylcyclopentane (2-methylcyclopentanecarbonitrile).


Step 3: Mendius Reduction of Nitrile
Finally, the nitrile group is reduced using sodium amalgam and ethanol (Na(Hg)/C2H5OH).
This reaction (known as the Mendius reduction) selectively reduces the cyano group (-CN) to a primary amine group (-CH2NH2).
Thus, the final major product P is 1-methyl-2-(aminomethyl)cyclopentane, which matches the structure shown in Option 1 (image_1.webp).

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