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Multiple Choice

Grignard reaction of an aldehyde (R'CHO) with RMgX yields on workup?

Grignard reagents are strong nucleophiles that add to carbonyls. When RMgX reacts with an aldehyde R'CHO, the R– from the Grignard adds to the carbonyl carbon, giving an alkoxide intermediate: R-CH(OMgX)-R'. After aqueous workup, the alkoxide is protonated to yield the alcohol: R-CH(OH)-R'. The carbon bearing the hydroxyl then has two carbon substituents (R and R' ), making it a secondary alcohol. This is different from a primary alcohol (which would arise if the aldehyde were formaldehyde) and from products like carboxylic acids or ethers that don’t form in this simple aldehyde-Grignard reaction.

Grignard reagents are strong nucleophiles that add to carbonyls. When RMgX reacts with an aldehyde R'CHO, the R– from the Grignard adds to the carbonyl carbon, giving an alkoxide intermediate: R-CH(OMgX)-R'. After aqueous workup, the alkoxide is protonated to yield the alcohol: R-CH(OH)-R'. The carbon bearing the hydroxyl then has two carbon substituents (R and R' ), making it a secondary alcohol. This is different from a primary alcohol (which would arise if the aldehyde were formaldehyde) and from products like carboxylic acids or ethers that don’t form in this simple aldehyde-Grignard reaction.