Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter Term	Chapter 13 Homework Answers

1. Predict the general features of the proton and C-13 NMR spectra of the following compounds. Use the format of question 2 below.

a) diethyl ketone

H NMR:
1-2 ppm, area 6, triplet (methyls)
2-3 ppm, area 4, quartet (methylenes)

13C NMR (proton uncoupled):
three peaks: ~30 ppm (methyls), ~50 ppm (methylenes), ~200 ppm (carbonyl)

b) p-ethylbenzoic acid

H NMR:
1-2 ppm, area 3, triplet (methyl)
2-3 ppm, area 2, quartet (methylene)
7-8 ppm, area 4, multiplet (aromatic)
11-12 ppm, area 1, singlet (carboxylic acid)

13C NMR (proton uncoupled):
seven peaks: ~30 ppm (methyl), ~50 ppm (methylene), 120-180 ppm (4 different aromatic carbons), ~200 ppm (carboxylic acid)

c) CH3-O-CH(CH3)-CH2-CH=O

H NMR:
1-2 ppm, area 3, doublet (methyl)
2-3 ppm, area 2, triplet (methylene) (actually a doublet of doublets)
3-4 ppm, area 3, singlet (methoxy)
3-4 ppm, area 1, multiplet (methine - CH) (actually a triplet of quartets)
9-10 ppm, area 1, triplet (aldehyde)

13C NMR (proton uncoupled):
five peaks: ~30 ppm (methyl), ~50 ppm (methylene), ~70 ppm (methoxy), ~80 ppm (methine - CH), ~200 ppm (carbonyl)

2. Identify the following compounds based on their proton NMR spectra:

a) C3H6O

2.72 ppm, area 2, quintet
4.73 ppm, area 4, triplet

b) C8H8O2

11.0 ppm, area 1, singlet
7.0 ppm, area 5, multiplet
3.0 ppm, area 2, singlet

c) C10H14

7.05 ppm, area 4, singlet
2.45 ppm, area 4, quartet
1.05 ppm, area 6, triplet

d) C3H6Br2

3.80 ppm, area 1, multiplet
3.50 ppm, area 2, doublet
1.12 ppm, area 3, doublet

e) C6H10

4.82 ppm, area 2, singlet
2.22 ppm, area 4, triplet
1.65 ppm, area 4, triplet