Textbook Question
Show how you would add a Grignard reagent to an ester or a nitrile to synthesize
(b) heptan-4-ol.
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22. Carboxylic Acid Derivatives: NAS
Lactones, Lactams and Cyclization Reactions
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Predict the major, organic product for the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the reactants: The starting material is a cyclic ester (lactone) and the reagent is an organolithium compound.
Understand the mechanism: Organolithium reagents are strong nucleophiles and bases. They will attack the electrophilic carbonyl carbon of the lactone, opening the ring.
Predict the intermediate: The nucleophilic attack by the organolithium reagent will result in the formation of an alkoxide intermediate after the ring opening.
Consider the quenching step: The addition of H⁺ (acid quench) will protonate the alkoxide intermediate, resulting in the formation of an alcohol.
Determine the major product: The major product will be an alcohol with the opened ring structure, where the organolithium reagent has added to the carbonyl carbon, forming a new carbon-carbon bond.
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