Which of the compounds will react faster

Question:

Which of the compounds will react faster in SN1 reaction with the –OH ion?

CH3— CH2— Cl or C6H5— CH2— Cl

Solution:

C6H5— CH2— Cl will react faster in an SN1 reaction with the OH- ion. This happens due to the stability of the carbocation in the compound. C6H5 group is already

stable due to resonance, and the CH2 attached will gain that stability, thus forming a stable C6H5CH2+ carbocation after the cleavage in the first step of the SN1

reaction.

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