Q30E - Organic Chemistry (Mcmurry)

Question

The conversion of 3° alcohols into 3° alkyl halides under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.

Step-by-Step Solution

Answer

Step 1: Substitution nucleophilic reaction

By the substitution nucleophilic reaction, they follow the bimolecular reaction, which is a two steps process:

1. Removal of the leaving group

2. Formation of the carbocation

3. Addition of the nucleophile

Step 2: Formation of compound a

By the SN₁ Reaction, the removal of the hydroxyl group occurs, followed by the formation of the cationic intermediate. the carbocation, and the addition of the nucleophile that is a chlorine halide. The formation of the desired product occurs as follows:

Step 3: Formation of compound b

By the SN₁ Reaction, the removal of the hydroxyl group occurs,  followed by the formation of the cationic intermediate, the carbocation, then the addition of the nucleophile that is a bromide ion halide. The formation of the desired product occurs as follows:

Step 4: Formation of compound c

By the SN₁ reaction, the removal of the hydroxyl group occurs, followed by the formation of the cationic intermediate, the carbocation, and the addition of the nucleophile that is a Br ion. The formation of the desired product occurs as follows: