Question Details

Isopropyl iodide is formed after reaction of propene with HI, this is due to

Options

A

more stable free radical

B

homolysis

C

more stable carbanion

D

more stable carbocation

Correct Answer :

more stable carbocation

Solution :

The correct option is more stable carbocation.

When propene reacts with hydroiodic acid (HI), it undergoes an electrophilic addition reaction. The reaction proceeds through a carbocation intermediate via Markovnikov's rule. Let's break down the step-by-step mechanism to understand why this happens:

Step 1: Protonation of the alkene
Propene (CH3-CH=CH2) reacts with the proton (H+) from the strongly acidic HI. The double bond acts as a nucleophile and attacks the proton. This protonation can theoretically yield two different carbocation intermediates depending on which carbon carbon double bond carbon accepts the proton:
1. If the proton adds to the central carbon (C-2), we obtain a primary carbocation:
CH3-CH+-CH3 (Incorrect, this is the secondary path)
Specifically, adding the proton to the terminal carbon (C-3) yields the secondary carbocation: CH3-CH+-CH3.
2. Adding the proton to the central carbon (C-2) yields a primary carbocation: CH3-CH2-CH2+.

Step 2: Stability of the carbocations
A secondary carbocation (CH3-CH+-CH3) is significantly more stable than a primary carbocation (CH3-CH2-CH2+) due to the electron-donating inductive effect (+I) of the two methyl groups and hyperconjugation involving six α-hydrogens. The primary carbocation has only one alkyl group and two α-hydrogens, making it much less stable.

Step 3: Attack of the nucleophile
Because the secondary carbocation is the more stable carbocation, the reaction proceeds almost exclusively through this intermediate. The iodide ion (I-) then attacks the positively charged central carbon of the secondary carbocation to form isopropyl iodide (CH3-CH(I)-CH3) as the major product.

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