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ns: O OH 1) MeMgBr 2) H2O (a) HO OH 1) Excess MeMgBr 2)

Chapter 13, Problem 13.5

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QUESTION:

ns: O OH 1) MeMgBr 2) H2O (a) HO OH 1) Excess MeMgBr 2) H2O (b) O O

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QUESTION:

ns: O OH 1) MeMgBr 2) H2O (a) HO OH 1) Excess MeMgBr 2) H2O (b) O O

ANSWER:

Step 1 of 7

(a) Mechanism:

In the first step, the carbon on the methyl Grignard group (which carries a full negative charge) acts as a nucleophile and attacks the electrophilic carbon of the ketones carbonyl group. This pushes the double bond elections up onto the oxygen of the ketone, forming a secondary alkoxide.

                     

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