Tutorial Chapter 3

1. Draw and name all isomers of:

a. C7H16
b. C8H18
c. C5H11Br
2. Locate and identify the functional groups in the following molecules. In these
representations, each intersection of lines and the end of each line represents a
carbon atom with the appropriate number of hydrogens attached.

3. Explain why each of the following names is incorrect:

a. 2,2-Dimethyl-6-ethylheptane
b. 4-Ethyl-5,5-dimethylpentane
c. 3-Ethyl-4,4-dimethylhexane
d. 5,5,6-Trimethyloctane
e. 2-Isopropyl-4-methylheptane
4. Consider 2-methylbutane (isopentane).Sighting along the C2C3 bond:
a. Draw a Newman projection of the most stable conformation.
b. Draw a Newman projection of the least stable conformation.
5. Assume that you have a variety of cyclohexanes substituted in the positions
indicated. Identify the substituents as either axial or equatorial. For example, a 1,2cis relationship means that one substituent must be axial and one equatorial,
whereas a 1,2-trans relationship means that both substituents are axial or both are
equatorial.
a.

1,3-Trans disubstituted

b.

1,4-Cis disubstituted

c.

1,3-Cis disubstituted

d.

1,5-Trans disubstituted

e.

1,5-Cis disubstituted

f.

1,6-Trans disubstituted

6. Which compound would you expect to be the more stable: cis-1,2dimethylcyclopropane or trans-1,2dimethylcyclopropane? Explain your answer.
7. Draw the two chair conformations of menthol,
and tell which is more stable.