Chapter 4
Alkanes and Cycloalkanes
Review of Concepts
Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of
Chapter 4. Each of the sentences below appears verbatim in the section entitled Review of Concepts and
Vocabulary.
Hydrocarbons that lack ____________ are called saturated hydrocarbons, or ___________.
__________rules provide a systematic way for naming compounds.
Rotation about C-C single bonds allows a compound to adopt a variety of __________________.
___________ projections are often used to draw the various conformations of a compound.
_____________ conformations are lower in energy, while ____________ conformations are
higher in energy.
The difference in energy between staggered and eclipsed conformations of ethane is referred to as
_____________ strain.
________ strain occurs in cycloalkanes when bond angles are less than the preferred _____°.
The _______ conformation of cyclohexane has no torsional strain and very little angle strain.
For a monosubstituted cyclohexane in a chair conformation, the substituent can occupy either an
axial or an ______________ position. These two possibilities represent two different
conformations that are in equilibrium with each other. The term ring flip is used to describe the
conversion of one conformation into the other. The equilibrium will favor the chair conformation
with the substituent in the _____________ position, because an axial substituent generates 1,3-
_________ interactions.
Review of Skills
Fill in the blanks and empty boxes below. To verify that your answers are correct, look in your textbook at
the end of Chapter 4. The answers appear in the section entitled SkillBuilder Review.
SkillBuilder 4.1 Identifying the Parent
Identify the parent in
each of the following
compounds.
SkillBuilder 4.2 Identifying and Naming Substituents
SkillBuilder 4.3 Identifying and Naming Complex Substituents
CHAPTER 4 111
SkillBuilder 4.4 Assembling the Systematic Name of an Alkane
SkillBuilder 4.5 Assembling the Name of a Bicyclic Compound
SkillBuilder 4.6 Identifying Constitutional Isomers
SkillBuilder 4.7 Drawing Newman Projections
SkillBuilder 4.8 Identifying Relative Energy of Conformations
SkillBuilder 4.9 SkillBuilder 4.10
Drawing a Chair Conformation Drawing Axial and Equatorial Positions
112 CHAPTER 4
SkillBuilder 4.11 Drawing Both Chair Conformations of a Monosubstituted Cyclohexane
SkillBuilder 4.12 Drawing Both Chair Conformations of Disubstituted Cyclohexanes
SkillBuilder 4.13 Drawing the More Stable Chair Conformation of Polysubstituted Cyclohexanes
Common Mistakes to Avoid
You might find that you struggle with problems that ask you to draw constitutional isomers. Don’t be
discouraged. Many students struggle with drawing constitutional isomers. In particular, it is sometimes
difficult to find ALL of the constitutional isomers with a particular molecular formula, and it is also difficult
to avoid drawing the same compound more than once. However, these skills will be critical as we progress
through the upcoming chapters. So, in order to get more proficient with constitutional isomers, do the
following:
1) Skip to Section 14.16 of your textbook (Hydrogen Deficiency Index: Degrees of Unsaturation),
and read that entire section (it is only a few pages, and you do not need any background to
understand that section in its entirety). Then, do SkillBuilder 14.4 (Calculating HDI), including
all of the problems in that SkillBuilder.
2) Review the methodical approach for drawing constitutional isomers that is presented in the
solution to problem 4.3.
3) Try to do problem 4.15, using the approach outlined in the solution to problem 4.3, and then
check the solution to problem 4.15 to make sure that you applied the approach correctly.
If you complete the three tasks above, you should gain confidence in your ability to draw constitutional
isomers and to avoid drawing the same isomer twice.