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Multiple Choice

What is the product of intramolecular dehydration of the alcohol with structure R-CH2-CH2OH?

Dehydration of an alcohol under acid gives an alkene by removing water across a beta hydrogen. The hydroxyl group is protonated to become a good leaving group, water departs, and a nearby beta hydrogen is removed to form a carbon–carbon double bond. For the molecule R-CH2-CH2OH, the leaving group comes from the terminal carbon, and the adjacent carbon (the one attached to R) supplies the beta hydrogen. Forming the double bond between these two carbons yields R-CH=CH2. That’s why the product is the alkene, not an oxidized product like an aldehyde or carboxylic acid.

Dehydration of an alcohol under acid gives an alkene by removing water across a beta hydrogen. The hydroxyl group is protonated to become a good leaving group, water departs, and a nearby beta hydrogen is removed to form a carbon–carbon double bond. For the molecule R-CH2-CH2OH, the leaving group comes from the terminal carbon, and the adjacent carbon (the one attached to R) supplies the beta hydrogen. Forming the double bond between these two carbons yields R-CH=CH2. That’s why the product is the alkene, not an oxidized product like an aldehyde or carboxylic acid.