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Organic Chemistry

Carey/Giuliano
8th edition
Chapter 3

Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Question 1
What is the relationship between the Newman
representations shown?

A) identical
B) constitutional isomers
C) different conformations of the same compound
D) stereoisomers

Question 2
What is the relationship between the Newman
representations shown?

A) identical
B) constitutional isomers
C) different conformations of the same compound
D) stereoisomers

Question 3
Select the least stable conformation of
ethylene glycol.
A)

B)

C)

D)

Question 4
Select the most stable conformation of
butanoic acid.
A)

B)

C)

D)

Question 5
Which compound has the greatest torsional
strain in the planar conformation?
A) cyclopropane
B) cyclobutane
C) cyclopentane
D) cyclohexane

Question 6
Rank the conformations of cyclohexane in
order of decreasing stability.
A) chair > half-chair > twist-boat
B) chair > twist-boat > half-chair
C) twist-boat > half-chair > chair
D) half-chair > twist-boat > chair

Question 7
The most stable conformation of cis-1-tertbutyl-4-methylcyclohexane has
A) both groups equatorial
B) both groups axial
C) the tert-butyl group axial and the methyl
equatorial
D) the tert-butyl group equatorial and the
methyl axial

Question 8
The most stable conformation of trans-1isopropyl-3-methylcyclohexane is:
A)

B)

C)

D)

Question 9
What is the relationship between the two chair
conformations below?

A) conformational isomers
B) constitutional isomers
C) different compounds
D) stereoisomers

Question 10
What is the relationship between the two
cyclohexane chairs below?

A) conformational isomers
B) constitutional isomers
C) stereoisomers
D) different compounds

Question 11
Which of the following statements is not true
concerning the chair-chair interconversion of
trans-1,2-diethylcyclohexane?
A) An axial group will be changed into the
equatorial position.
B) The energy of repulsions present in the
molecule will be changed.
C) Formation of the cis substance will result.
D) One chair conformation is more stable
than the other

Question 12
Which of the listed terms best describes the
relationship between the methyl groups in
the chair conformation of the substance
shown?
A) eclipsed
B) trans
C) anti
D) gauche

Question 13
Which of the following has an equatorial methyl group
in its most stable conformation?
A)

B)

C)

D)

Question 14
The structure shown is the carbon skeleton of
adamantane, a hydrocarbon having a
structure that is a section of the diamond
lattice. Adamantane is:
A) bicyclic
B) tricyclic
C) tetracyclic
D) pentacyclic

Question 15
Which structure has the most strain?
A) the eclipsed conformation of ethane
B) the gauche conformation of butane
C) the boat conformation of cyclohexane
D) the skew boat conformation of
cyclohexane

Question 16
What is the IUPAC name for the compound
represented by the Newman projection?

A) 1-tert-Butyl-1-isopropylethane
B) 1-tert-Butyl-3-methylbutane
C) 2-isopropyl-3,3-dimethylbutane
D) 2,2,3,4-tetramethylpentane

Question 17
Which one of the following statements is true?
A) Van der Waals strain in cis-1,2dimethylcyclopropane is the principal reason
for its decreased stability relative to the trans
isomer.
B) Cycloalkanes larger than cyclodecane rarely
occur naturally because they are too strained.
C) One mole of cyclohexane gives off less heat
on being burned in air than one mole of any
other cycloalkane.
D) The principal source of strain in the gauche
conformation of butane is torsional strain.

Question 18
Which of the following statements best
describes the most stable conformation of
trans-1,3-dimethylcyclohexane?
A) Both methyl groups are axial.
B) Both methyl groups are equatorial.
C) One methyl groups is axial, the other
equatorial.
D) The molecule is severely strained and
cannot exist.

Question 19
What is the relationship between the two
structures shown?
A) Constitutional isomers
B) Stereoisomers
C) Different drawings of the
same conformation of
the same compound.
D) Different conformations of the same
compound.

Question 20
The most stable conformation of the compound
to the right has
A) an axial methyl group and
an axial ethyl group.
B) an axial methyl group and
an equatorial ethyl group.
C) an equatorial methyl group and an
equatorial ethyl group.
D) an equatorial methyl group and an axial
ethyl group.

Answer Key Chapter 3


1.
2.
3.
4.
5.
6.
7.
8.
9.
10.

C
B
C
B
D
B
D
B
A
C

11.
12.
13.
14.
15.
16.
17.
18.
19.
20.

C
D
D
B
C
D
A
C
A
D