1.

b) a) Explain the mechanism of Snl reactiontaking 2-bromo-2-methylpropane(t-Butylbromide) (2M)

Answer»

The central carbon is surrounded by three bulky groups apart from Br, which is a good leaving group.

Hence if Br leaves first, a stable, less sterically hindered and planar carbocation (stabilised by the +I effect of 3 -CH3 groups) is formed in the first step, which is then susceptible to attack in the second step by the incoming OH- group (from either sides), forming a tertiary alcohol. This whole process depicts SN1 mechanism:

Slow, rate determining step (CH3)3 CBr → (CH3)3 C+ + Br-

Fast step (CH3)3 C+ + OH-→ (CH3)3 COH



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