Chem 335 - Winter 2002
Organic Chemistry II
Dr. Carl C. Wamser

Chapter 13 Homework

Carey, pages 536 - 545:
Problems 13.21-34, 38, 40

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