교과서 질문
There were actually two possible products in the solvolysis reaction from Figure 21.10. Show both products. Which would you expect to be more stable? Why?
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7. Substitution Reactions
SN1 Reaction
객관식
Which of the following alkyl halides would undergo an reaction the fastest?
A
(tert-butyl bromide)
B
(ethyl bromide)
C
(benzyl bromide)
D
(methyl bromide)
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검증된 단계별 안내1
Recall that an SN1 reaction proceeds via a two-step mechanism where the rate-determining step is the formation of a carbocation intermediate after the leaving group departs.
Identify the stability of the carbocation that would form from each alkyl halide. More stable carbocations form faster, thus increasing the SN1 reaction rate.
Consider the types of carbocations: tertiary (3°) carbocations are more stable than secondary (2°), which are more stable than primary (1°), and methyl carbocations are the least stable.
Analyze each alkyl halide: tert-butyl bromide forms a tertiary carbocation, ethyl bromide forms a primary carbocation, benzyl bromide forms a resonance-stabilized benzylic carbocation, and methyl bromide forms a methyl carbocation.
Compare the stability order: resonance-stabilized benzylic carbocations and tertiary carbocations are generally the most stable, so the alkyl halide that forms the most stable carbocation will undergo SN1 the fastest.
