Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol? A)The carbon in the alcohol is sp² hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol. B)The carbon in the carboxylic acid is sp³ hybridized and has a lower percent s-character that shortens the C-O bond in the carboxylic acid. C)The carbon in the carboxylic acid is sp hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid. D)The carbon in the carboxylic acid is sp² hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.

Question

Quizplus · Accepted Answer

The correct answer is D because carboxylic acid has a sp2-hybridized carbon atom in the carbonyl group, thus having a higher percentage of s-character in the hybridized orbital that overlaps with the oxygen p-orbital in the C-O bond. This results in a shorter C-O bond length compared to the C-O bond in alcohol, which has a sp3-hybridized carbon atom with a lower percentage of s-character.

Why Is the C-O Single Bond of a Carboxylic Acid