Question
By which mechanism would the following reaction proceed? please explain answer of why each is wrong or right. Thank you.

acetone . + L + BUONa Buona acetone Br OSNI OSN2 Ο Ε1 O E2 OSN1 and E1
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Answer #1

Sodium tert butoxide is a weak nucleophile therefore option SN2 is neglected.

Since acetone is used, it does not solvate the intermediate carobcation and therefore E2 elimination is favoured over E1 and SN1 where carbocation is stabilized by the solvent.

Thus option SN1 and E1 is neglected due to poor solvation of the intermediate.

Therefore Reaction favoured in above example is E2

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