Chem 335 - Winter 1999 - Organic Chemistry II
Portland State University - Dr. Carl C. Wamser

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Chapter 13 Homework

Brown & Foote, pages 495 - 504 :
Problems 13.12 - 13 , 15 - 22 , 27 , 29

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