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Ch. 18 - Ketones and Aldehydes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 18, Problema 29b

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(b)

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Step 1: Analyze the starting material and the product. The starting material is a cyclohexane ring with a ketone group and an aldehyde group. The product has a cyclohexane ring with an alcohol group, a methyl group, and an aldehyde group. This indicates that the ketone group is converted into a tertiary alcohol, and a methyl group is added.
Step 2: To convert the ketone group into a tertiary alcohol, perform a nucleophilic addition reaction using a Grignard reagent. Prepare the Grignard reagent, CH3MgBr, which will add a methyl group to the ketone carbon.
Step 3: React the starting material with the Grignard reagent (CH3MgBr) in an ether solvent. This will result in the formation of a tertiary alcohol at the ketone position, with the methyl group added.
Step 4: After the Grignard reaction, perform an acidic workup (e.g., using H3O+) to protonate the alkoxide intermediate and yield the final tertiary alcohol product.
Step 5: Verify that the aldehyde group remains intact throughout the reaction sequence, as it is not reactive under the conditions used for the Grignard reaction.

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