Question

Tryptophan is one of the amino acids typically found in proteins. (a) What is the hybridization at the numbered C, N, and O atoms? (Type your answer using the format sp3 for sp3.) 1 2 3 4 5 6 (b) How many bonds are present in tryptophan? sigma bonds (c) Predict the bond angles at points a, b, and c. a <109.5° 120° 180° b <109.5° 120° 180° c <109.5° 120° 180°

Answer 1

(a) What is the hybridization at the numbered C, N, and O atoms? (Type your answer using the format sp3 for sp3.) 1 2 3 4 5 6

Carbon from the carboxilic acid --> SP2

carbons from benzene ring --> SP2

All other carbons --> SP3

Nitrogens from ring --> SP2

Nitrogen from amino group --> SP2

Oxygen atoms --> SP2 from C=O group

Oxygen atom --> SP3 from C-O-H

(b) How many bonds are present in tryptophan? sigma bonds

sigma bonds -->

C-C = 11

C-H = 8

O-H = 1

C-O = 1

C-N = 3

N-H = 3

Total = 27

(c) Predict the bond angles at points a, b, and c. a <109.5° 120° 180° b <109.5° 120° 180° c <109.5° 120° 180°

most likely:

C=C --> 120

C=O --< 120

-N- --> 120

C-O-H --< 180