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Mechanism of solvolyses of substituted benzyl bromides in 80 % ethanol

The mechanism of solvolysis of activated and deactivated benzyl bromides in 80 % ethanol at 25 °C has been investigated by using the Yukawa-Tsuno treatment and by correlating measured kinetic data with relative stabilities of corresponding benzyl carbocations calculated at the IEFPCM M06-2X/6- 311+G(3df, 3pd) level of theory. Both correlation methods demonstrate that only benzyl bromides substituted with strong para-π-donors solvolyze by the SN1 mechanism whereas other activated and deactivated substrates solvolyze by the SN2 mechanism.

benzyl bromide ; IEFPCM ; M06-2X ; SN1 ; SN2 ; solvolysis ; Yukawa-Tsuno

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