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Tutorial Chapter 3

This document outlines 7 tutorial questions covering topics such as: 1. Drawing isomers of alkanes and identifying functional groups in molecules. 2. Explaining why several alkane names are incorrect. 3. Drawing Newman projections and identifying axial and equatorial substituents in cyclohexanes. 4. Comparing the stability of cis and trans cyclopropane isomers and determining the more stable chair conformation of menthol.

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146 views1 page

Tutorial Chapter 3

This document outlines 7 tutorial questions covering topics such as: 1. Drawing isomers of alkanes and identifying functional groups in molecules. 2. Explaining why several alkane names are incorrect. 3. Drawing Newman projections and identifying axial and equatorial substituents in cyclohexanes. 4. Comparing the stability of cis and trans cyclopropane isomers and determining the more stable chair conformation of menthol.

Uploaded by

ShahrizatSmailKassim
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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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.

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