Question Details

Which one of the following alcohols reacts instantaneously with Lucas reagent?

Options

A

C H 3 C H 2 C H 2 C H 2 O H

B

C H 3 C H 2 C | H C H 3 O H

C

C H 3 C | H C H 3 C H 2 O H

D

C H 3 C | C H 3 | C H 3 O H

Show Answer

Correct Answer :

Option D

C H 3 C | C H 3 | C H 3 O H

C H 3 C | C H 3 | C H 3 O H

Solution :

The correct answer is:
C H 3 C | C H 3 | C H 3 O H

Step-by-step Explanation:

1. Understanding Lucas Reagent and the Reaction Mechanism
Lucas reagent is a mixture of concentrated hydrochloric acid (HCl) and anhydrous zinc chloride (ZnCl2). It is used to distinguish between primary, secondary, and tertiary alcohols.
The reaction proceeds via a nucleophilic substitution mechanism (SN1), where the rate-determining step is the formation of a carbocation intermediate.

2. Stability of Carbocations
The rate of reaction of alcohols with Lucas reagent depends directly on the stability of the carbocation formed during the reaction:
Tertiary (3°) carbocation>Secondary (2°) carbocation>Primary (1°) carbocation

3. Reactivity Behavior
- Tertiary alcohols (3°) react instantaneously with Lucas reagent to produce turbidity (cloudiness due to the formation of insoluble alkyl chlorides) at room temperature.
- Secondary alcohols (2°) react within 5 to 10 minutes.
- Primary alcohols (1°) do not produce turbidity at room temperature unless heated.

4. Analyzing the Options
Let us determine the degree of each given alcohol:
1. CH3CH2CH2CH2OH (Butan-1-ol): The OH group is attached to a primary carbon. This is a primary (1°) alcohol.
2. CH3CH2CH(CH3)OH (Butan-2-ol): The OH group is attached to a carbon that is bonded to two other carbons. This is a secondary (2°) alcohol.
3. CH3CH(CH3)CH2OH (Isobutyl alcohol): The OH group is attached to a primary carbon. This is a primary (1°) alcohol.
4. (CH3)3COH (2-Methylpropan-2-ol / tert-Butyl alcohol): The OH group is attached to a tertiary carbon (a carbon bonded to three other methyl groups). This is a tertiary (3°) alcohol.

Since tertiary alcohols form the highly stable tertiary carbocation intermediate, 2-methylpropan-2-ol reacts instantaneously with Lucas reagent at room temperature to form a precipitate of tert-butyl chloride.

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