Question

Tertiary butyl bromide react with aqueous NaOH by SN1 mechanism while n-butyl bromide reacts with SN2 mechanism.why?

Answer 1

because SN1 takes place via carbo cation formation and tertiary carbo cation is more stable while theSN2 mechanism takes place via nucleophilic attack and hence it is easier on primary carbon rather than secondary or tertiary carbon.

Answer 2

Dear Student,

◆ Explanation -

• Reaction of alkyl bromides with aq.NaOH takes place as nucleophilic substitution reaction.

(I) Tertiary butyl bromide -

• Tertiary butyl bromide forms tertiary butyl carbocation.
• As tertiary butyl carbocation is more stable, it undergoes first nucleophilic substitution (SN1) reaction.

(II) N-butyl bromide -

• N-butyl bromide forms n-butyl carbocation.
• As n-butyl carbocation allows less hindrance around the central atom, it undergoes second nucleophilic substitution (SN2) reaction.

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