1. Bruice, Organic Chemistry, 6e
PROBLEM 3 ♦ How many signals would you expect to see in the 1H NMR spectrum of each of the following compounds?
Bruice, Organic Chemistry, 6e

2. Bruice, Organic Chemistry, 6e
PROBLEM 4 How could you distinguish the 1H NMR spectra of the following compounds?
PROBLEM 5 ♦
There are three isomeric dichlorocyclopropanes. Their 1H NMR spectra show one signal for isomer 1, two signals for isomer 2, and three signals for isomer 3. Draw the structures of isomers 1, 2, and 3.
Bruice, Organic Chemistry, 6e

3. Bruice, Organic Chemistry, 6e
PROBLEM 15 ♦ How would integration distinguish the 1H NMR spectra of the following compounds?
PROBLEM 19 Explain how the following compounds, each with the same molecular formula, could be distinguished by their 1H NMR spectra.
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

4. Bruice, Organic Chemistry, 6e
PROBLEM 17 ♦ Which of the following compounds is responsible for the 1H NMR spectrum shown in Figure 14.10?
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

5. Bruice, Organic Chemistry, 6e
PROBLEM 18 ♦ One of the spectra in Figure is produced by 1-chloropropane and the other by 1-iodopropane. Which is which?
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

6. Bruice, Organic Chemistry, 6e
PROBLEM 21 ♦ The 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown in Figure (below). Identify the carboxylic acids. (The “offset” notation means that the farthest-left signal has been moved to the right by the indicated amount in order to fit on the spectrum; thus, the signal at 9.8 ppm offset by 2.4 ppm has an actual chemical shift of 12.2 ppm.)
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

7. Bruice, Organic Chemistry, 6e
PROBLEM 21 ♦ The 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown in Figure (below). Identify the carboxylic acids. (The “offset” notation means that the farthest-left signal has been moved to the right by the indicated amount in order to fit on the spectrum; thus, the signal at 9.8 ppm offset by 2.4 ppm has an actual chemical shift of 12.2 ppm.)
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

8. Bruice, Organic Chemistry, 6e
PROBLEM 26 ♦ Identify each compound from its molecular formula and its 1H NMR spectrum: a. C9H12
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

9. Bruice, Organic Chemistry, 6e
PROBLEM 26 ♦ Identify each compound from its molecular formula and its 1H NMR spectrum: b. C5H10O
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.

10. Bruice, Organic Chemistry, 6e
PROBLEM 26 ♦ Identify each compound from its molecular formula and its 1H NMR spectrum: c. C9H10O2
Bruice, Organic Chemistry, 6e
© 2011 Pearson Education, Inc.