Nmr Practice Problems Worksheet Page 8
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915) A small plant was adding bromine across the double bond of 2-butene to make 2,3-dibromobutane. A
controller malfunction and allowed the reaction temperature to rise beyond safe limits. A careful
distallation of the product showed that several impurities had formed, including the one whose NMR is
shown below. Determine the structure.
1.00
2.01
2.00
3.00
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
16) When 2-chloro-2-methylbutane is treated with a variety of strong bases, the products always seem contain
two isomers (A and B) of formula C5H10. When sodium hydroxide is used as the base isomer B
predominates. Determine the structures of A and B and explain the experimental results.
A)
1.00
9.00
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
B)
2.01
2.01
3.01
3.00
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
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