What is the IUPAC name for the following
molecule?
1. 1-(2-methylbutyl)-cyclopentane
2. 2-(3-methylbutyl)-cyclopentane
3. 2-(2-methylbutyl)-cyclopentane
4. (1,2-dimethylpropyl)-cyclopentane
5. (2,2-dimethylpropyl)-cyclopentane
Answer
4. (1,2-dimethylpropyl)-cyclopentane
How many secondary hydrogens are
there in the cycloalkane shown below?
1. 2
2. 3
3. 4
4. 5
5. 6
Answer
3. 4
Glucosamine (R = H), a naturally occurring substance
found in the exoskeleta of marine invertebrates, is believed
by some to be helpful in relieving arthritic symptoms in
humans. What are, respectively, the relative positions of
the amino group to the CH2OH substituent and OR group?
OH
O glucosamine
HO
HO OR
NH2
1. cis, cis
2. trans, trans
3. cis, trans
4. trans, cis
5. cannot be determined from this kind of perspective
drawing
Answer
2. trans, trans
What kind of strain is relieved the most
by ring puckering in cyclopentane?
1. torsional
2. steric
3. angle
4. steric and angle
5. torsional and steric
Answer
1. torsional
a) b) c) d) e)
Which of the above molecules represents the most stable
conformation of trans-1,3-dimethylcyclohexane?
1. a
2. b
3. c
4. d
5. e
Answer
4. d
Which of the following may not contribute
to the overall energy of a cycloalkane?
1. torsional strain
2. angle strain
3. hydrogen bonding
4. steric strain
5. All of these contribute to the overall
energy of a cycloalkane.
Answer
3. hydrogen bonding
Which of the following statements is true?
1. An axial group encounters more steric strain
than an equatorial group.
2. All substituted cycloalkanes possess axial and
equatorial bonds.
3. Only cyclopentane rings possess axial and
equatorial bonds.
4. Cyclohexane derivatives are more stable with
axial substituents than with equatorial
substituents.
5. A cyclic compound cannot contain a double
bond.
Answer
1. An axial group encounters more steric
strain than an equatorial group.
Which of the following statements is true concerning
the isomers cis-1,2-dimethylcyclohexane and cis-1,3-
dimethylcyclohexane?
1. They are not constitutional isomers.
2. They represent different conformations of the
same molecule.
3. The favored conformer of the 1,3-isomer is more
stable than that of the 1,2-isomer.
4. The favored conformer of the 1,3-isomer and that
of the 1,2-isomer are equal in energy.
5. The relative stability of the two molecules cannot
be determined.
Answer
3. The favored conformer of the 1,3-
isomer is more stable than that of
the 1,2-isomer.
What isomer of dichlorocyclohexane is
represented by the Newman projection shown
below?
Cl H
H Cl
H H
H H
1. 1-axial; 3-axial
2. 1-equatorial; 4-equatorial
3. 1-equatorial; 3-equatorial
4. 1-equatorial; 3-axial
5. 1-equatorial; 4-axial
Answer
5. 1-equatorial; 4-axial
a) b) c) d) e)
Which of the above structures represents the most
stable conformation of 1-tert-butyl-3,5-
dimethylcyclohexane?
1. a
2. b
3. c
4. d
5. e
Answer
4. d
What is the energy difference between the two
chair conformations of trans-1,2-
dimethylcyclohexane?
1. zero
2. one gauche interaction
3. two gauche interactions
4. three gauche interactions
5. four gauche interactions
Answer
4. three gauche interactions
What happens to a substituent in a chair
conformation of cyclohexane when all bonds
rotate in a synchronized fashion?
1. nothing, it stays where it was
2. it “flips” to an alternative position on the same
carbon
3. it moves to the next carbon
4. the carbon to which the substituent is attached
changes hybridization
5. it moves from a cis to a trans position
Answer
2. it “flips” to an alternative position on
the same carbon
Dipole moments usually are measured on
collections of molecules, and represent average
values for all conformations present. Which of the
following collections of molecules will not show a
dipole moment?
1. 1,2-dibromoethane
2. trans-1,2-dibromocyclohexane
3. cis-1,2-dibromocyclohexane
4. cis-1,4-dibromocyclohexane
5. trans-1,4-dibromocyclohexane
Answer
5. trans-1,4-dibromocyclohexane
a) b) c) d) e)
Which of the above will have the highest energy
after the chair flip?
1. a
2. b
3. c
4. d
5. e
Answer
2. b
What are the relative geometries of ring fusions
(starting from the left) for the steroid shown
below?
H3C R
H3C
H
H H
1. cis, cis, cis
2. cis, cis, trans
3. cis, trans, trans
4. trans. cis, cis
5. trans, trans, cis
Answer
3. cis, trans, trans