Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2008

Chapter 13 Homework

Carey, end-of-chapter problems
ARIS Problems

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

b) p-ethylbenzoic acid

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

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