Which reaction in the following pair will take place more rapildy? (CH3)3CBr (H2

Question

Which reaction in the following pair will take place more rapildy? (CH3)3CBr (H20) --> (CH3)3COH + HBr OR (CH3)3CBr (CH3CH2OH) --> (CH3)3COCH2CH3 + HBr

Explanation / Answer

(CH3)3CBr (H20) --> ( The symmetry favored conrotatory concerted path would generate a very strained trans-cyclohexene double bond, and is energetically unlikely. Instead, a higher activation energy bond cleavage to a diradical intermediate takes place on heating. The racemic diastereomer of this compound undergoes the same ring opening at a lower temperature, and this is believed to be a concerted conrotatory electrocyclic reaction..

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