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Organic Chemistry II |
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Professor Carl C. Wamser |
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Chem 335 - Winter 2005 |
Chapter 13 Workshop |
|
Organic Chemistry II |
|
Professor Carl C. Wamser |
||
Chem 335 - Winter 2005 |
Chapter 13 Workshop |
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)
Materials adapted from:
Peer-Led Team Learning: Organic Chemistry, 1/e
Jack A. Kampmeier, University of Rochester
Pratibha Varma-Nelson, St. Xavier University
Donald Wedegaertner, University of the Pacific
Prentice-Hall, 2001, ISBN 0-13-028413-0
http://www.sci.ccny.cuny.edu/~chemwksp/OrganicChem.html