Spectroscopy

1. Draw the structural formulas of the following compounds and indicate the number of NMR
   signals that would be expected for each compound.
   (a) methyl iodide
   (b) 2,4-dimethylpentane
   (c) cyclopentane
   (d) propylene (propene)

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1. Draw the structural formula of the compounds that are indicated by the following data:
   (a) an alkyl halide with a molecular formula of C3H7Cl whose NMR spectrum contains two
   signals: a doublet (6H), and a multiplet (1H).
   (b) a compound with molecular formula C7H14Cl2 whose NMR spectra contains three signals: a singlet (9H), a triplet (3H), and a quartet (2H).
2. Figures 3-7 are representative spectra of compounds. Based on the NMR
   Figure 5
   Figure 6

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Figure 7
Figure 8

c 2011 Advanced Instructional Systems, Inc. and George Wahl and Maria Gallardo-Williams

Sample Solution