Organic Chemistry A Brief Course International Edition 13th Edition by David J. Hart - Test Bank
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Organic Chemistry A Brief Course International Edition 13th Edition by David J. Hart - Test Bank

Organic Chemistry A Brief Course International Edition 13th Edition by David J. Hart - Test Bank   Instant Download - Complete Test Bank With Answers     Sample Questions Are Posted Below   Chapter 5 -- Stereoisomerism MULTIPLE CHOICE 1.Which of the following objects is chiral? A) egg B) pencil C) cross country skis D) …

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Organic Chemistry A Brief Course International Edition 13th Edition by David J. Hart – Test Bank

 

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Sample Questions Are Posted Below

 

Chapter 5 — Stereoisomerism
MULTIPLE CHOICE
1.Which of the following objects is chiral?
A) egg
B) pencil
C) cross country skis
D) paperclip
E) shoes
ANS: E TOP: Definitions
2.Chiral molecules that have nonsuperimposable mirror images are called:
A) enantiomers
B) diastereomers
C) meso compounds
D) stereogenic
E) symmetrical
ANS: A TOP: Definitions
3.Which of the following molecules has a mirror plane of symmetry?
A) 1
B) 2
C) 3
D) 4
E) all of them
ANS: B TOP: Definitions
4.What is the process that separates enantiomers?
A) separation
B) decoupling
C) resetting
D) resolution
E) selective binding
ANS: D TOP: Definitions
5.A 50:50 mixture of enantiomers
A) is a meso form.
B) is a pair of diastereomers.
C) is a racemic mixture.
D) rotates plane polarized light.
E) is a pair of conformers.
ANS: C TOP: Definitions
6.The terms that best describe the isomeric relationship between staggered and eclipsed ethane are
A) configurational, achiral, diastereomers.
B) conformational, chiral, enantiomers.
C) conformational, achiral, diastereomers.
D) configurational, chiral, enantiomers.
E) conformational, achiral, enantiomers.
ANS: C TOP: Definitions
7.Which of the molecules below has a stereogenic carbon atom?
A) 1
B) 2
C) 3
D) 2 and 3
E) 1, 2, and 3
ANS: B TOP: Definitions
8.How many stereogenic centers are present in the following molecule?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS: B TOP: Definitions
9.How many stereogenic centers are present in the following molecule?
A) 1
B) 2
C) 4
D) 6
E) 8
ANS: B TOP: Definitions
10.How many chiral stereoisomers can be drawn for CH3CHClCHBrCH3?
A) 1
B) 2
C) 3
D) 4
E) 8
ANS: D TOP: Definitions
11.How many stereogenic carbons are in the following molecule?
A) 0
B) 1
C) 2
D) 3
E) 4
ANS: A TOP: Definitions
12.How many stereoisomers can be obtained from the monobromination of pentane?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS: B TOP: Definitions
13.How many stereoisomers with the formula CH3CHICHICH3 are possible?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS: C TOP: Definitions
14.The number of stereogenic centers in progesterone is:
progesterone (no stereochemistry shown)
A) 2
B) 3
C) 4
D) 5
E) 6
ANS: E TOP: Definitions
15.The total number of possible stereoisomers of   is:
A) 2
B) 4
C) 6
D) 8
E) 0
ANS: D TOP: Definitions
16.The total number of possible stereoisomers of 1-bromo-2-chlorocyclopentane is:
A) 2
B) 4
C) 6
D) 8
E) 0
ANS: B TOP: Definitions
17.An unknown sample is tested with a polarimeter for optical activity.  The results of the test required no movement of the analyzer.  What samples would give this result?
A) pure enantiomer
B) meso compound
C) racemic mixture
D) both B and C
E) none of these
ANS:DTOP:Optical Activity
18.An unknown sample is tested with a polarimeter for optical activity. The results of the test require movement of the analyzer. What samples would give this result?
A) pure enantiomer
B) meso compound
C) racemic mixture
D) both B and C
E) none of these
ANS:ATOP:Optical Activity
19.Which of the following statements about enantiomers is INCORRECT?
A) they cannot be differentiated by spectra
B) they have the same melting and boiling points
C) the mirror image of the R enantiomer is the S enantiomer
D) the specific rotation of enantiomers has the same magnitude
E) without exception, S enantiomers will rotate plane-polarized light to the left (counterclockwise)
ANS:ETOP:Optical Activity
20.The observed rotation for 100 mL of an aqueous solution containing 1 g of sucrose, placed in a 2-decimeter sample tube, is +1.33° at 25°C.  What is the specific rotation of sucrose?
A) +66.5°
B) +266°
C) +41.5
D) +133°
E) 108°
ANS:ATOP:Optical Activity
21.Which of the following molecules are the same?
A) 1 and 2
B) 3 and 4
C) 1 and 3
D) 2 and 3
E) 2 and 4
ANS:CTOP:Relationships Between Stereoisomers
22.Which of the three molecules below is the enantiomer of the following molecule?
A) I
B) II
C) III
D) there are no enantiomers
E) both II and III
ANS:ATOP:Relationships Between Stereoisomers
23.Which of the three molecules below is a diastereomer of the following molecule?
A) I
B) II
C) III
D) there are no diastereomers
E) both I and II
ANS:CTOP:Relationships Between Stereoisomers
24.Which of the following are achiral conformers?
A) staggered and eclipsed forms of ethane
B) cis and trans-2-butene
C) meso and (2R,3R)-2,3-dibromobutane
D) (R) and (S)-lactic acid
ANS:ATOP:Relationships Between Stereoisomers
25.Which of the following would constitute a pair of enantiomers?
A) staggered and eclipsed forms of ethane
B) cis and trans-2-butene
C) meso- and (2R,3R)-2,3-dibromobutane
D) (2R,3R) and (2S,3S)-tartaric acid
E) none of these
ANS:DTOP:Relationships Between Stereoisomers
26.The terms that best describe the relationship between (2R,3S)-2,3-butanediol and (2S,3S)-2,3-butanediol are
A) configurational, diastereomers.
B) conformational, enantiomers.
C) conformational, diastereomers
D) configurational, enantiomers.
E) configurational, cis/trans.
ANS:ATOP:Relationships Between Stereoisomers
27.The terms that best describe the relationship between (2R,3S)-2-bromo-3-chlorobutane and (2S,3R)-2-bromo-3-chlorobutane are
A) configurational, achiral, diastereomers.
B) conformational, chiral, diastereomers.
C) configurational, chiral, enantiomers.
D) conformational, chiral, enantiomers.
E) configurational, chiral, diastereomers.
ANS:CTOP:Relationships Between Stereoisomers
28.Which of the following statements about the pair of molecules shown below is not true?
A) They have the same boiling point.
B) One rotates plane polarized light in the opposite direction from the other.
C) They have the same density.
D) One rotates plane polarized light a different number of degrees than the other.
E) They are mirror images of each other.
ANS:DTOP:Relationships Between Stereoisomers
29.According to the R-S convention, which priority is correct for the following sets of groups?
A) NH2 > Cl > CH3 > H
B) Cl > NH2 > CH3 > H
C) Cl > CH3 > NH2 > H
D) H > Cl > CH3  > NH2
E) CH3 > NH2 > Cl > H
ANS: B TOP: The R-S and E-Z Conventions
30.(R)-2-chlorobutane is correctly represented by which of the following:
A) I
B) II
C) III
D) IV
E) V
ANS: B TOP: The R-S and E-Z Conventions
31.Which of the following groups has the highest priority for assigning R-S absolute configuration?
A) CH2=CH–
B) (CH3)2CH–
C) (CH3)3C–
D) CH3CH2–
E) CH3–
ANS: C TOP: The R-S and E-Z Conventions
32.The correct IUPAC name for the following molecule is:
A) (E)-2-bromo-3-chloro-5-methyl-2-hexene
B) (E)-2-bromo-3-chloro-5-methyl-3-hexene
C) (Z)-2-bromo-3-chloro-5-methyl-3-hexene
D) (Z)-2-bromo-3-chloro-5-methyl-2-hexene
E) (E)-5-bromo-4-chloro-2-methyl-4-hexene
ANS: D TOP: The R-S and E-Z Conventions
33.Which of the following structures is (E)-2,3-dichloro-2-pentene?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS: E TOP: The R-S and E-Z Conventions
34.Of the following structures, how many are classified “E”?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS: C TOP: The R-S and E-Z Conventions
35.Of the following structures, how many are classified “Z”?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS: C TOP: The R-S and E-Z Conventions
36.Which of the following structures depicts (R)-3-ethyl-2,3-dimethylhexane?
A)
 D)
B)
 E)
C)
ANS: B TOP: The R-S and E-Z Conventions
37.The priority order for R/S nomenclature is
A) —CH=CH2 > —OH > —CH3 > —CH2CH3
B) —OH > —CH2CH3 > —CH=CH2 > —CH3
C) —OH > —CH=CH2 > —CH2CH3 > —CH3
D) —CH3 > —CH2CH3 > —CH=CH2 > —OH
E) —CH2CH3 > —CH3 > —CH=CH2 > —OH
ANS: C TOP: The R-S and E-Z Conventions
38.Which name describes the following structure?
A) (R)-3-methyl-1-penten-3-ol
B) (S)-3-methyl-1-penten-3-ol
C) (R)-3-ethyl-1-buten-3-ol
D) (R)-3-methyl-1-pentyn-3-ol
E) (S)-3-ethyl-1-buten-3-ol
ANS: A TOP: The R-S and E-Z Conventions
39.Which name describes the following structure?
A) (R)-4-methyl-1-hexen-4-ol
B) (S)-4-ethyl-1-penten-4-ol
C) (R)-4-ethyl-1-penten-3-ol
D) (S)-4-methyl-1-hexen-4-ol
E) (S)-4-methyl-1-hexyn-4-ol
ANS: D TOP: The R-S and E-Z Conventions
40.What is correct name for the following structure?
A) (R,S)-2,3-dichlorobutane
B) (2R,3S)-2,3-dichlorobutane
C) (2S,3S)-2,3-dichlorobutane
D) (2R,3R)-2,3-dichlorobutane
E) none of these
ANS: D TOP: Fischer and Newman Projections
41.What is the absolute configuration around C-2 and C-3?
A) R, R
B) S, S
C) R, S
D) S, R
E) E, Z
ANS: A TOP: Fischer and Newman Projections
42.The absolute configuration around the stereogenic center of the molecule below is:
A) R
B) S
C) E
D) Z
E) trans
ANS: A TOP: Fischer and Newman Projections
43.The Fischer projection formula for (S)-lactic acid (2-hydroxypropanoic acid) is
A)
 D)
B)
 E)
C)
ANS: E TOP: Fischer and Newman Projections
44.The Fischer projection that represents the same molecule as   is:
A)
 D)
B)
 E)
C)
ANS: C TOP: Fischer and Newman Projections
45. represents
A) (2R,3R)-2,3-butanediol.
B) (2S,3S)-2,3-butanediol.
C) the most stable conformer of (2R,3R)-2,3-butanediol.
D) the least stable conformer of (2R,3R)-2,3-butanediol.
E) meso-2,3-butanediol.
ANS: E TOP: Fischer and Newman Projections
46.Which one of the following structures represents a meso compound?
A)
 D)
B)
 E)
C)
ANS: A TOP: Fischer and Newman Projections
47.When (R)-3-bromo-2-methyl-1-butene is reacted with HBr, two stereoisomers are formed.  What is the relationship of these stereoisomers?
A) enantiomers
B) meso compounds
C) diastereomers
D) E
E) Z
ANS:CTOP:Stereochemistry and Chemical Reactions
48.Treating 1-butene with HBr produces a product with one stereogenic carbon.  What is the name of the product?
A) 2-bromo-1-butene
B) 1-bromobutane
C) (R)-2-bromobutane
D) (S)-2-bromobutane
E) both C and D in equal amounts
ANS:ETOP:Stereochemistry and Chemical Reactions
49.When (S)-3-bromo-1-butene is treated with HBr, two stereoisomeric products form.  What is the relationship of these two products?
A) enantiomers
B) diastereomers
C) meso compounds
D) racemic mixture
E) cis/trans
ANS:BTOP:Stereochemistry and Chemical Reactions
50.How many stereogenic carbons are produced from the following sequence of reactions?
A) 1
B) 2
C) 3
D) 4
E) 5
ANS:BTOP:Stereochemistry and Chemical Reactions
51.Enantiomers may differ in the following property:
A) the rate at which they react with a chiral reagent
B) boiling point
C) melting point
D) number of degrees they rotate plane polarized light
E) solubility in water
ANS:ATOP:Stereochemistry and Chemical Reactions
52.The product of addition of bromine to (R)-3-buten-2-ol will be
A) a 50:50 mixture of enantiomers.
B) a mixture of enantiomers formed in unequal amounts.
C) a 50:50 mixture of diastereomers.
D) a mixture of diastereomers formed in unequal amounts.
E) optically inactive.
ANS:DTOP:Stereochemistry and Chemical Reactions

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