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How do organometallic reagents react with ketones to form tertiary alcohols?
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organometallic compound
The periodic table of the elements, displaying the group numbers and the s, p, d, and f blocks. Elements in the shaded area are the metals of organometallic chemistry.
Organometallic reagents, such as Grignard reagents and organolithium compounds, are highly effective in organic synthesis due to the nucleophilic or carbanion character of the organic group bonded to the electropositive metal.12
When these reagents react with a ketone, the process occurs in two primary stages:
- Nucleophilic Attack: The organic group of the organometallic reagent acts as a nucleophile and attacks the electrophilic carbonyl carbon of the ketone. This addition results in the formation of a metal alkoxide intermediate (such as ROMgX for Grignard reagents).21
- Hydrolysis: The intermediate is subsequently treated with water or a dilute acid in a process called hydrolysis. This step protonates the alkoxide, yielding the final tertiary alcohol product.123
This reaction is a fundamental method for constructing carbon-carbon bonds and is widely used in laboratory settings to synthesize various alcohols.13