Workshop 13

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Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2004

Chapter 13 Workshop

Spectroscopy

1. Identify compounds of the given molecular formula that show only one 1-H NMR signal:

C2H6O

C3H4

C2H4Br2

C4H6

C5H12

C5H10

2. Identify compounds of the given molecular formula that show only two 1H NMR signals:

C3H6Cl2

C3H6O2

C3H8O2

C2H5OCl

3. How many 1H NMR signals will each of the following compounds show?

a) (CH3)3CCH2CH3

b) CH3COCOOCH3

c) CH3COCH2COCH3

d) CH3COCH2CH2COCH3

e) CH3COCH2CH2COOCH3

f) CH3COCH2CHClCOCH3

4. Deduce the unknown structures from the data presented.

a) C4H8O triplet (1.0 ppm, 3H) singlet (2.1 ppm, 3H) quartet (2.4 ppm, 2H)

b) C4H8O2 triplet (1.2 ppm, 3H) singlet (2.1 ppm, 3H) quartet (4.1 ppm, 2H)

c) C8H8O singlet (2.4 ppm, 3H) multiplet (7.5 ppm, 5H)

d) C2H5BrO singlet (3.3 ppm, 3H) singlet (4.9 ppm, 2H)

e) C4H9Br doublet (1.1 ppm, 6H) multiplet (1.9 ppm, 1H) doublet (3.4 ppm, 2H)

f) C4H8O3 triplet (1.3 ppm, 3H) quartet (3.7 ppm, 2H) singlet (4.2 ppm, 2H) singlet (11.0 ppm, 1H)

g) C3H7ClO triplet (1.4 ppm, 3H) quartet (3.8 ppm, 2H) singlet (5.6 ppm, 2H)

h) C6H12O2 singlet (1.2 ppm, 6H) singlet (2.1 ppm, 3H) singlet (2.8 ppm, 2H) singlet (3.7 ppm, 1H)

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