Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB, or E2, and predict the product of each:

Question

Tell whether each of the following reactions is likely to be [latex] S_{N}1, S_{N}2[/latex], E1, E1cB, or E2, and predict the product of each:

Strategy

Look carefully in each reaction at the substrate, leaving group, nucleophile, and solvent. Then decide from the preceding summary which kind of reaction is likely to be favored.

Accepted Answer

(a) A secondary, nonallylic substrate can undergo an [latex]S_{N}2[/latex] reaction with a good nucleophile in a polar aprotic solvent but will undergo an E2 reaction on treatment with a strong base in a protic solvent. In this case, E2 reaction is likely to predominate.

(b) A secondary benzylic substrate can undergo an[latex]S_{N}2[/latex] reaction on treatment with a nonbasic nucleophile in a polar aprotic solvent and will undergo an E2 reaction on treatment with a base. Under protic conditions, such as aqueous formic acid ([latex]HCO_{2}H[/latex]), an [latex]S_{N}1[/latex] reaction is likely, along with some E1 reaction.

Question 12.6: Tell whether each of the following reactions is likely to be...

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