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Provide a combination of an organolithium and a ketone/aldehyde that can produce the following alcohol.

A. Grignard reagent; formaldehyde
B. Organolithium reagent; ketone
C. Grignard reagent; ketone
D. Organolithium reagent; aldehyde

Answer :

Final answer:

To produce alcohols, a Grignard or an Organolithium reagent is reacted with an aldehyde or a ketone, generating an alkoxide intermediate that yields the alcohol upon protonation. The type of resulting alcohol—primary, secondary, or tertiary—depends on the carbonyl compound used.

Explanation:

To produce different types of alcohols, one can combine an organometallic reagent such as a Grignard or an Organolithium reagent with a carbonyl compound like an aldehyde or a ketone. Specifically:

  • Grignard reagent with formaldehyde will yield a primary alcohol (1° alcohol).
  • Organolithium reagent with a ketone will result in the formation of a tertiary alcohol (3° alcohol).
  • Grignard reagent with a ketone will also yield a tertiary alcohol (3° alcohol).
  • Organolithium reagent with an aldehyde will produce a secondary alcohol (2° alcohol).

The reaction mechanism involves nucleophilic addition of the organometallic reagent to the carbonyl carbon of the aldehyde or ketone, leading to an alkoxide intermediate. Upon protonation, this intermediate yields the corresponding alcohol. Aldehydes generally give secondary alcohols, while ketones yield tertiary alcohols. An exception is formaldehyde, which reacts to form primary alcohols due to it having no alkyl substituents.

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