Predict whether each of the following substitution reactions is likely to be SN1 or SN2:

Question

Predict whether each of the following substitution reactions is likely to be [latex]S_{N}1[/latex] or [latex]S_{N}2[/latex]:

Strategy

Look at the substrate, leaving group, nucleophile, and solvent. Then decide from the summaries at the ends of Sections 12-7 and 12-9 whether an [latex]S_{N}1[/latex] or an [latex]S_{N}2[/latex] reaction is favored. [latex]S_{N}1[/latex] reactions are favored by tertiary, allylic, or benzylic substrates, by good leaving groups, by nonbasic nucleophiles, and by protic solvents. [latex]S_{N}2[/latex] reactions are favored by primary substrates, by good leaving groups, by good nucleophiles, and by polar aprotic solvents.

Accepted Answer

(a) This is likely to be an [latex]S_{N}1[/latex] reaction because the substrate is secondary and benzylic, the nucleophile is weakly basic, and the solvent is protic.

(b) This is likely to be an [latex]S_{N}2[/latex] reaction because the substrate is primary, the nucleophile is a reasonably good one, and the solvent is polar aprotic.

Question 12.3: Predict whether each of the following substitution reactions...

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