Textbook Question
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(a)
21. Aldehydes and Ketones: Nucleophilic Addition
Organometallics on Ketones
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Provide the major product for the following reaction.
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Verified step by step guidance1
Identify the reactants: The starting material is a ketone, specifically 2-butanone, and the reagent is a sodium acetylide (NaC≡C-CH3) followed by an acidic workup (H3O+).
Understand the reaction type: This is a nucleophilic addition reaction where the acetylide ion acts as a nucleophile and attacks the electrophilic carbonyl carbon of the ketone.
Mechanism step 1: The acetylide ion (C≡C-CH3) attacks the carbonyl carbon of 2-butanone, breaking the C=O double bond and forming an alkoxide intermediate.
Mechanism step 2: The alkoxide intermediate is then protonated by the hydronium ion (H3O+) during the acidic workup, resulting in the formation of an alcohol.
Determine the major product: The major product will be a tertiary alcohol with the acetylide group attached to the former carbonyl carbon, resulting in a new carbon-carbon bond.
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