Which of the following is the major product in the electrophilic addition of hcl to (3s)-2,3-dimethylpent-1-ene?

a. (3s)-3-chloro-2,3-dimethylpentane exclusively

b. (3r)-2-chloro-2,3-dimethylpentane exclusively

c. 2-chloro-2,3-dimethylpentane racemic mixture of two enantiomers

d. (3s)-2-chloro-2,3-dimethylpentane exclusively

e. (2r,3s)-1-chloro-2,3-dimethylpentan e exclusively

(3S)-2-chloro-2,3-dimethylpentane is produced exclusively.

Explanation:

Electrophilic addition to (3S)-2,3-dimethylpent-1-ene proceeds through a carbocationic intermediate.

In the first step, adds onto double bond to produce more stable tertiary carbocation. (protonation)

In the second step, adds onto carbocation to produce (3S)-2-chloro-2,3-dimethylpentane exclusively.(nucleophilic addition)

So, option (d) is correct.

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