Attempted Grignard reaction of cyclohexanone with tert-butylmagnesium bromide gives only

Chapter 22, Problem 22.48

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Attempted Grignard reaction of cyclohexanone with tert-butylmagnesium bromide gives only about 1% yield of the expected addition product along with 99% unreacted cyclohexanone. If D3O1 is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it. Explain. + 1% 99% 1. (CH3)3CMgBr 2. D3O+ O C(CH3)3

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