Question

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 carboxylic acid is sp hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.
B) The carbon in the carboxylic acid is sp^3 hybridized and has a lower percent s-character that shortens the C-O bond in the carboxylic acid.
C) The carbon n the alcohol is sp^2 hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol.
D) The carbon in the carboxylic acid is sp^2 hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.

Answer 1

The C-O bond in carboxylic acids is shorter than in alcohols due to the sp² hybridization and higher s-character of the carbon in the carboxylic acid, which makes the bond stronger and shorter. The correct answer is D.

Step-by-step explanation:

The reason the C-O single bond in a carboxylic acid is shorter than the C-O single bond in an alcohol is related to the hybridization of the carbon atom bonded to the oxygen in each case. In a carboxylic acid, the carbon atom is part of a carbonyl group, which means it is sp2 hybridized and hence has a higher percentage of s-character in its bonds. The greater s-character contributes to stronger and shorter bonds because the electrons are held closer to the nucleus.

On the other hand, the carbon in an alcohol is sp3 hybridized, with less s-character, thus resulting in a longer C-O bond.

Considering the options provided, the correct answer is 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.