Organic Chemistry
Carey/Giuliano
Chapter 4
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Question 1
Which of the following compounds is chiral?
A) 2-methyl-2-pentanol
B) 2-bromobutane
C) methylcyclohexane
D) 2-propanol
Question 2
Which of the molecules below is optically
active?
A) 1 only
B) 1 and 3
C) 1 and 2
D) 1, 2 and 3
Question 3
How many chirality centers are in the molecule
shown at the right?
A) 1
B) 2
C) 3
D) 4
Question 4
How many chirality centers are in the molecule
shown at the right?
A) 1
B) 2
C) 3
D) 4
Question 5
Determine the absolute configuration of the
molecule shown.
A) (S)
B) (R)
C) not optically active
Question 6
What is the absolute configuration of the
molecule shown?
A) (R)
B) (S)
C) not optically active
Question 7
What is the relationship between the Fischer
projections shown?
A) identical
B) enantiomers
C) diastereomers
D) different compounds
Question 8
Determine the relationship between the
compounds shown below.
A) identical
B) enantiomers
C) diastereomers
D) meso
Question 9
Which conformation shown is
(S)-bromochlorofluoromethane?
A)
B)
C)
D)
Question 10
Which one of the following groups has the
highest ranking when precedence is
assigned according to the Cahn-IngoldPrelog rules?
A) -CH=CH2
B) -CH=O
C) -CH2CH2Br
D) -CH2F
Question 11
Which one of the following compounds is
chiral?
A) 1-methylcyclohexanol
B) cis-2-methylcyclohexanol
C) trans-4-methylcyclohexanol
D) cyclohexanol
Question 12
Which one of the following is achiral?
A) 2-chloropentane
B) 3-chloropentane
C) 1,2-dichloropentane
D) 1,3-dichloropentane
Question 13
Which one of the following has the most
stereoisomeric forms?
A) 2-chloro-1-butene
B) 2-chloro-2-butene
C) 5-chloro-2-pentene
D) 4-chloro-2-pentene
Question 14
Which one of the following is a diastereomer of
meso-3,4-dibromohexane?
A) threo-2,4-dibromohexane
B) (2R, 5R)-2,5-dibromohexane
C) (3R, 4R)-3,4-dibromohexane
D) (3R, 4S)-3,4-dibromohexane
Question 15
Which one of the following statements is false?
A) A racemic mixture is achiral.
B) A compound can contain more than one
stereogenic center and be achiral.
C) A compound can contain more than one
stereogenic center and be chiral.
D) Any compound that contains a plane of
symmetry is achiral.
Question 16
A certain substance (+)-X, when optically pure,
has a specific rotation [α] of +40o. A
mixture of (+)-X and its enantiomer (-)-X has
o
a specific rotation of -8 . What percent of
the mixture is (+)-X?
A) 30%
B) 35%
C) 40%
D) 45%
Question 17
(+)-Glucose has the Fischer projection shown.
How many compounds are diastereomers
of (+)-glucose?
A) 8
B) 14
C) 15
D) 16
Question 18
Which compound gives only a single
stereoisomer of 1,3-dimethylcyclopentane
on catalytic hydrogenation?
A)
B)
C)
D) both A and B
Question 19
Which one of the following is
(R)-2-bromobutane?
A)
B)
C)
D)