Textbook Question
What products are formed when the following compounds react with CH3MgBr, followed by the addition of dilute acid? Disregard stereoisomers.
a. b. c.
21. Aldehydes and Ketones: Nucleophilic Addition
Organometallics on Ketones
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Provide the major product for the following reaction dealing with the Grignard reagent.
A
B
C
D
Verified step by step guidance1
Identify the functional groups in the starting material. The compound has a ketone group (C=O) and an amine group (NH2).
Recognize the Grignard reagent, CH3MgBr, which acts as a nucleophile. It will attack the electrophilic carbon of the carbonyl group (C=O) in the ketone.
The nucleophilic carbon from the Grignard reagent will form a bond with the carbonyl carbon, resulting in the formation of an alkoxide intermediate.
After the Grignard addition, the reaction mixture is treated with an acid (H3O+), which protonates the alkoxide to form an alcohol.
The major product will be a tertiary alcohol, where the original ketone carbon is now bonded to the methyl group from the Grignard reagent and the hydroxyl group (OH) from the protonation step.
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