Increasing order of reactivity of the following compounds for S_N1 substitution is:
(A) (CH3)2CH–CH2–Cl
(B) CH3–CH2–CH2–Cl
(C) p-OCH3–C6H4–CH2–Cl
(D) C6H5–CH2–CH2–Cl

Question

Accepted Answer

(B) < (A) < (D) < (C). SN1 rate follows carbocation stability. (C) p-methoxybenzyl gives a resonance- and OMe-stabilized benzylic cation (most reactive). (A), (B), (D) all ionize to primary cations; the accepted order is (B) < (A) < (D) < (C).

Increasing order of reactivity of the following compounds for S_N1 substitution is: (A) (CH3)2CH–CH2–Cl (B) CH3–CH2–CH2–Cl (C) p-OCH3–C6H4–CH2–Cl (D) C6H5–CH2–CH2–Cl

Solution

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