Answer to Question #134805 in Organic Chemistry for Brayen

Question

In small peptides, six atoms associated with the peptide bond lie in a single plane. These are the alpha C, the carbonyl C, and the carbonyl O of the left-side amino acid, and the amino nitrogen, the hydrogen attached to the nitrogen, and the alpha C of the right-side amino acid. This coplanarity requires that the hybridize of the carbonyl C and the amino nitrogen both be
Select one:
a. sp
b. sp2
c. sp3
d. Trick question. The hybridization varies with the side chain.

Answer 1

Solution.

In the amide group –CO-NH - the carbon atom exists in the form of sp2 hybridization. For example, the electron pair of a nitrogen atom is paired with the π electrons of the double bond between carbon and oxygen. Then the electron density of the peptide group will shift to oxygen. As a result of this conjugation, the bond lengths inside the radical are aligned.

sp2-hybridization

Answer:

sp2-hybridization