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

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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?

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

ANS: E TOP: Fischer and Newman Projections

44.The Fischer projection that represents the same molecule as is:

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?

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

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