McMurry, pp 405 - 409:
Problems 13.18-20, 23, 26-36, 38-41, 49-52
1. Predict the general features of the H and 13C 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 H 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