Chapter 5 Stereoisomerism Complete Test Bank

Organic Chemistry, 4e (Klein)

Chapter 5 Stereoisomerism

1) What is the relationship between the following two compounds?

Two bond-line structures represent two different compounds. The first compound has a SMILES string of CCCCC. The second compound has a SMILES string CCC(C)C.

A) constitutional isomers

B) stereoisomers

C) identical

D) not isomers; different compounds entirely

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

2) What is the relationship between the following two compounds?

Two bond-line structures represent two different compounds. The first compound has a four-carbon chain, in which C 2 is wedge bonded to a methyl group. The second compound has a four-carbon chain, in which C 2 is dash bonded to a methyl group.

A) constitutional isomers

B) stereoisomers

C) identical

D) not isomers; different compounds entirely

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

3) What is the relationship between the following two compounds?

Two bond-line structures represent two different compounds. The first compound has a SMILES string of CC[C@@H](C)O. The second compound has a SMILES string of CC[C@H](C)O.

A) constitutional isomers

B) stereoisomers

C) identical

D) not isomers; different compounds entirely

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

4) What is the relationship between the following two compounds?

$Two bond-line structures represent two different compounds. The first compound has a SMILES string of C/C=C/C. The second compound has a SMILES string of C/C=C\C.$

A) constitutional isomers

B) stereoisomers

C) identical

D) not isomers; different compounds entirely

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

5) What is the relationship between the following two compounds?

Two bond-line structures represent two different compounds. The first compound has a chair conformation of a cyclohexane ring. The second compound is the mirror image of the first compound.

A) constitutional isomers

B) stereoisomers

C) identical

D) not isomers; different compounds entirely

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

6) What is the relationship between the following two compounds?

Two bond-line structures represent two different compounds. The first compound has a SMILES string of CC[C@@H](C)O. The second compound has a SMILES string of CCOCC.

A) constitutional isomers

B) stereoisomers

C) identical

D) not isomers; different compounds entirely

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

7) Which term best describes the alkene below?

The bond-line structure of the compound has a SMILES string of C/C=C/OC.

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

8) Which term best describes the alkene below?

The bond-line structure of the compound has a SMILES string of CC=C(F)C.

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

9) Which term best describes the alkene below?

The bond-line structure of the compound has a SMILES string of C/C=C/C.

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

10) Which term best describes the alkene below?

The bond-line structure of the compound has a SMILES string of C1CCC=CC1.

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 1

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

11) Which term best describes the alkene below?

$The bond-line structure of the compound has a SMILES string of O1\C(OCCC1)=C/C.$

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 2

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

12) Shown below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Which term describes the double bond indicated by the arrow?

The structure of rosuvastatin has a SMILES string of CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)/C=C/[C@H](C[C@H](CC(=O)O)O)O, in which an arrow points toward the double bond between C 1 and C 2 that is bonded to C 5 of the pyrimidine ring.

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 2

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

13) Shown below is the structure of Singulair® (montelukast), a medication used to manage asthma. Is the alkene of montelukast cis, trans, or neither?

The structure of montelukast has a SMILES string of CC(C)(c1ccccc1CC[C@H](c2cccc(c2)/C=C/c3ccc4ccc(cc4n3)Cl)SCC5(CC5)CC(=O)O)O.

A) cis only

B) trans only

C) both terms may be used

D) neither cis nor trans

Diff: 2

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

14) What is the total number of isomers with the molecular formula C4H8?

A) 2

B) 3

C) 6

D) 8

E) 9

Diff: 3

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

15) Which arrow(s) indicates chiral center(s) in the compound shown?

The structure of the compound has a SMILES string of CC1(CCCC2(C1CC=C(C2(C=O)O)C=O)C)C, in which the following carbon positions are labeled with an arrow: C 8 a is labeled as a, the carbonyl carbon bonded to C 2 is labeled as b, C 1 is labeled as c, C 4 a is labeled as d, and C 3 is labeled as e.

A) a and b

B) c, and e

C) c and d

D) a, c, and d

E) b, c, and e

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

16) Which arrow(s) indicates chiral center(s) in nicotine, the molecule shown below?

The structure of the compound has a SMILES string of CN1CCCC1c2cccnc2, in which the following carbon positions are labeled with an arrow: C 3 of the cyclopentane ring is labeled a, C 2 is labeled b, C 5 is labeled c, C 1 of the pyridine ring is labeled d, and N 3 is labeled e.

A) a

B) b

C) c and d

D) d and e

E) a, b, and d

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

17) Which arrow indicates the chiral center in the compound shown?

The structure of the compound has a SMILES string of C(=O)OCC(CO)O, in which the following carbon positions are labeled with an arrow: the carbonyl carbon is labeled as a, the oxygen atom bonded to C 1 is labeled b, C 3 is labeled c, C 2 is labeled d, and C 1 is labeled e.

A) a

B) b

C) c

D) d

E) e

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

18) Which arrow(s) indicates the chiral center(s) in the compound shown?

The structure of the compound has a pyranose ring, in which C 1, C 2, C 3, and C 4 are each bonded to a hydroxyl group, and C 5 is bonded to C 6 that is further bonded to a hydroxyl group. The following carbon atom positions are labeled with an arrow: C 5 is labeled a, C 1 is labeled b, C 2 is labeled c, C 3 is labeled d, and C 4 is labeled e.

A) a

B) a and b

C) a and d

D) c, d, and e

E) a, b, c, d, and e

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

19) Which arrow(s) indicates the chiral center(s) in the compound shown?

The structure of the compound has a SMILES string of CC(C(c1ccccc1)O)N, in which the following carbon positions are labeled with an arrow: C 1 of the benzene ring is labeled a, C 1 of the carbon chain is labeled b, C 2 of the carbon chain is labeled c, C 3 of a benzene ring is labeled d, and C 4 is labeled e.

A) a

B) b

C) a and b

D) b and c

E) d and e

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

20) Identify the relationship between the following structures.

Two bond-line structures represent two different compounds. The first compound has a four-carbon chain, in which C 2 is wedge bonded to a hydroxyl group at the bottom. The second compound has a four-carbon chain, in which C 2 is wedge bonded to a hydroxyl group at the top.

A) enantiomers

B) identical

C) neither

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

21) Identify the relationship between the following structures.

Two bond-line structures represent two different compounds. The first compound has a SMILES string of CC[C@@H](C)O. The second compound is the mirror image of the first compound.

A) enantiomers

B) identical

C) neither

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

22) Identify the relationship between the following structures.

Two bond-line structures represent two different compounds. The first compound has a SMILES string of CC[C@@H](C)O. The second compound has a four-carbon chain, in which C 2 is dash bonded to a hydroxyl group.

A) enantiomers

B) identical

C) neither

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

23) Identify the relationship between the following structures.

A) enantiomers

B) identical

C) neither

Diff: 1

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

24) Identify the relationship between the following structures.

Two bond-line structures represent two different compounds. The first compound has a five-carbon chain, in which C 3 is wedge bonded to a hydroxyl group. The second compound is similar to the first compound, except that the wedge bond is replaced with a dash bond.

A) enantiomers

B) identical

C) neither

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

25) Which of the choices is an enantiomer of the compound shown?

An illustration shows a compound along with four possible structures of enantiomer, labeled 1 through 4 (in Roman Numerals).
The compound has a cyclohexene ring fused to a cyclohexane ring with a wedge bonded methyl group at the top and dash bonded hydrogen atom at the bottom fusion site.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

26) Which of the choices is an enantiomer of the compound shown?

An illustration shows a compound along with four possible structures of enantiomer, labeled 1 through 4 (in Roman Numerals).
The compound has a 5-membered ring made of four carbon and one nitrogen atom. N 1 is further single bonded to a methyl group. C 2 is wedge bonded to a pyridine ring.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

27) Which of the choices is an enantiomer of the compound shown?

An illustration shows a compound along with four possible structures of enantiomer, labeled 1 through 4 (in Roman Numerals).
The compound has a benzene ring. C 1 is single bonded to a 3-carbon chain, in which C 1 and C 2 are wedge bonded to a hydroxyl group and an amino group, respectively.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

28) Which of the choices is an enantiomer of the compound shown?

An illustration shows a compound along with four possible structures of enantiomer, labeled 1 through 4 (in Roman Numerals).
The compound has a 6-membered ring made of an oxygen atom and five carbon atoms. C 1 and C 4 are each dash bonded to a hydroxyl group. C 2 and C 3 are each wedge bonded to a hydroxyl group. C 5 is wedge bonded to a hydroxymethyl group.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

29) Which of the choices is an enantiomer of the compound shown?

An illustration shows a compound along with four possible structures of enantiomer, labeled 1 through 4 (in Roman Numerals).
The compound has an acetyl group bonded to an oxygen atom, which is further bonded to a 2-carbon chain, in which C 2 is wedge bonded to a hydroxyl group and single bonded to another hydroxyl group.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers

30) Assign the absolute configuration of the chiral center as R or S.

The bond-line structure of the compound has a SMILES string of CN1CCC[C@H]1c2cccnc2.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

31) Assign the absolute configuration of the chiral center as R or S.

The bond-line structure of the compound has a SMILES string of O=C(OC[C@@H](O)CO)C.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

32) Assign the absolute configuration of the chiral center as R or S.

The bond-line structure of the compound has a SMILES string of CC[C@@H](C)O.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

33) Assign the absolute configuration of the chiral center as R or S.

The bond-line structure of the compound has a SMILES string of CC[C@H](C)O.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

34) Assign the absolute configuration of the chiral center as R or S.

$The bond-line structure of the compound has a SMILES string of O[C@H]1\C=C/CC1.$

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

35) Assign the absolute configuration of the chiral center as R or S.

The bond-line structure of the compound has a five-carbon chain, in which C 1 is bonded to a hydroxyl group and wedge bonded to a methyl group.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

36) The structure shown is Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chiral carbons as R or S.

The structure of rosuvastatin has a SMILES string of CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)/C=C/[C@H](C[C@H](CC(=O)O)O)O.

A) There are two chiral carbons: one is S, the other is R

B) There are two chiral carbons: both centers are R

C) There are two chiral carbons: both centers are S

D) There are more than two chiral carbons in Crestor

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

37) The structure shown is Singulair® (montelukast), a medication used to manage asthma. Assign the absolute configuration of the chiral center as R or S.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

38) The structure shown is Plavix® (clopidogrel), a medication used to manage blood clots. Assign the absolute configuration of the chirality center as R or S.

The bond-line structure of clopidogrel has a SMILES string of COC(=O)[C@H](c1ccccc1Cl)N2CCc3c(ccs3)C2.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

39) The structure shown is Cymbalta® (duloxetine), a medication used to manage depression. Assign the absolute configuration of the chiral center as R or S.

The bond-line structure of duloxetine has a SMILES string of CNCC[C@@H](c1cccs1)Oc2cccc3c2cccc3.

A) R

B) S

C) R and S are both possible

D) The chiral center is neither R or S

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

40) What is the appropriate IUPAC name for compound shown?

The bond-line structure of the compound has a five-carbon chain, in which C 2 is wedge bonded to a hydroxyl group and C 4 is bonded to a methyl group.

A) (R)-4-methyl-2-pentanol

B) (S)-4-methyl-2-pentanol

C) (R)-2-methyl-4-pentanol

D) (S)-2-methyl-4-pentanol

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

41) What is the appropriate IUPAC for the compound shown?

The bond-line structure of the compound has a SMILES string of O[C@@H](CC)CCCCC.

A) (R)-6-octanol

B) (S)-6-octanol

C) (R)-3-octanol

D) (S)-3-octanol

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

42) Which of the following is the correct structure for (R)-2-pentanol?

Four bond-line structures represent four different compounds. The first compound has a cyclopentane ring, in which C 1 is wedge bonded to a hydroxyl group. The second compound has a SMILES string of CCC[C@@H](C)O. The third compound has a SMILES string of CCC[C@H](C)O. The fourth compound has a five-carbon chain, in which C 2 is wedge bonded to a hydroxyl group and C 4 is bonded to a methyl group.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

43) Which of the following is the correct structure for (S)-3-methylheptane?

Four-bond-line structures represent four different compounds. The first compound has a SMILES string of CCCC[C@H](C)CC. The second compound has a seven-carbon chain, in which C 3 is dash bonded to a methyl group. The third compound has a SMILES string of CCC[C@@H](C)CC. The fourth compound has a SMILES string of CCCC(C)CC.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

44) Which of the following structures is (S)-3-methylheptane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

45) Which of the following structures is (R)-4-ethyloctane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

46) Which of the following is the correct IUPAC name of the following structure?

The bond-line structure of the compound has a six-carbon chain, in which C 2 is bonded to a methyl group and C 3 is dash bonded to an ethyl group.

A) (S)-3-ethyl-2-methylhexane

B) (R)-3-ethyl-2-methylhexane

C) (S)-3-ethyl-2-methylpentane

D) (R)-3-ethyl-2-methylpentane

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

47) What is the correct IUPAC name of the following structure?

The bond-line structure of the compound has a SMILES string of CCCC[C@H](C)CC.

A) (S)-2-ethylhexane

B) (S)-3-methylheptane

C) (R)-2-ethylhexane

D) (R)-3-methylheptane

Diff: 2

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

48) Which choice correctly represents the structure below as a wedge-dash structure with any/all stereocenters correctly labeled with their absolute configuration?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

49) Which choice correctly represents the structure below as a wedge-dash structure with any/all stereocenters correctly labeled with their absolute configuration?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

50) Identify the relationship between the following structures.

A) diastereomers

B) enantiomers

C) the same compound

D) different compounds

Diff: 3

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

51) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -F II. -H III. -OH IV. -SH

A) I > II > III > VI

B) IV > I > III > I

C) III > IV > II > I

D) II > I > III > IV

E) IV > III > II > I

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

52) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -CH3 II. -CN III. -CH2OH IV. -Br

A) I > II > III > VI

B) IV > I > III > I

C) III > IV > II > I

D) II > I > III > IV

E) IV > III > II > I

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

53) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -CH2CH3 II. -CHCH2 III. -CCH IV. -CH3

A) III > IV > II > I

B) I > II > III > VI

C) IV > I > III > I

D) III > II > I > IV

E) IV > III > II > I

Diff: 1

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

54) What is the % ee of a sample of carvone that exhibits a specific rotation of −20, given that the specific rotation of (R)-carvone is −61?

A) 20%

B) 33%

C) 50%

D) 61%

E) 66%

Diff: 2

Learning Objective: 5.4 Compare the effects of a pair of enantiomers on plane-polarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light

55) What is the % ee of a sample of carvone that exhibits a specific rotation of −40, given that the specific rotation of (R)-carvone is −61?

A) 20%

B) 33%

C) 50%

D) 61%

E) 66%

Diff: 2

56) If a sample of carvone gives a specific rotation of −60 and the specific rotation of (R)-carvone is −61, does the unknown sample primarily have the R or S absolute configuration?

A) R

B) S

C) It is a racemic mixture.

D) This cannot be determined from the information given

Diff: 2

57) If a sample of carvone gives a specific rotation of 0 and the specific rotation of pure (R)-carvone is −61, what is the configuration of the unknown sample?

A) R

B) S

C) It is a racemic mixture.

D) This cannot be determined from the information given

Diff: 2

58) What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of −52?

A) −61

B) 64

C) 0

D) 61

Diff: 2

59) What is the specific rotation of a sample of carvone that is an equal mixture of the R and S enantiomers? (R)- carvone has a specific rotation of −61.

A) −61

B) 64

C) 0

D) 61

Diff: 2

60) What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 10, given that the specific rotation of (R)-carvone is −61?

A) 42

B) 84

C) 16

D) 58

Diff: 3

61) What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is −61?

A) 26%

B) 51%

C) 49%

D) 75%

Diff: 2

62) What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 10, given that the specific rotation of (R)-carvone is −61?

A) 42

B) 84

C) 16

D) 58

Diff: 3

63) What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is −61?

A) 25.5%

B) 51%

C) 49%

D) 74.5%

Diff: 2

64) What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of −20, given that the specific rotation of (R)-carvone is −61?

A) 20%

B) 66.5%

C) 33.5%

D) 61%

Diff: 2

65) What is the percentage of the R enantiomer in a sample of limonene that has a specific rotation of −38, given that the specific rotation of (S)-limonene is −116?

A) 20%

B) 66%

C) 33.3%

D) 61%

E) 32.7%

Diff: 2

66) The structure of Crestor (rosuvastatin), a medication used to reduce cholesterol, is shown. If the specific rotation for this compound is known to be +100, what would be the specific rotation for the stereoisomer shown at the right?

Two bond-line structures represent the structure of crestor and its stereoisomer structure. The structure of crestor has a SMILES string CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)/C=C/[C@H](C[C@H](CC(=O)O)O)O. The structure of stereoisomer of crestor has a SMILES string of CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)/C=C/[C@@H](C[C@@H](CC(=O)O)O)O.

A) +100

B) -100

C) 0

D) Impossible to predict

Diff: 2

67) Identify the relationship between the following structures.

An illustration shows the relationship between two bond-line structures. The first structure has a SMILES string of C[C@H[([C@@H](c1ccccc1)O)NC. The second structure has a SMILES string of C[C@H[([C@H](c1ccccc1)O)NC.

A) enantiomers

B) diastereomers

C) constitutional isomers

D) identical

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

68) Identify the relationship between the following structures.

An illustration shows the relationship between two bond-line structures. The first structure has a benzene ring, in which C 1 is bonded to C 1 of a three-carbon chain. In the carbon chain, C 1 is wedge bonded to a hydroxyl group and C 2 is wedge bonded to an N H group that is further bonded to a methyl group. The second structure has a SMILES string of C[C@H[([C@H](c1ccccc1)O)NC.

A) enantiomers

B) diastereomers

C) constitutional isomers

D) identical

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

69) Identify the relationship between the following structures.

An illustration shows the relationship between two bond-line structures. The first structure has a SMILES string of C([C@@H]1C(=C(C(=O)O1)O)O)O. The second structure has a furanose ring, in which C 1 is double bonded to an oxygen atom, C 2 is double bonded to C 3, C 2 and C 3 are each bonded to a hydroxyl group, and C 4 is dash bonded to C 5 that is further bonded to a hydroxyl group.

A) enantiomers

B) diastereomers

C) constitutional isomers

D) identical

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

70) Identify the relationship between the following structures.

A) enantiomers

B) diastereomers

C) constitutional isomers

D) identical

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

71) Identify the relationship between the following structures.

An illustration shows the relationship between two bond-line structures. The first structure has a SMILES string of C([C@@H]1[C@@H]([C@H](C(=O)O1)O)O)O. The second structure has a SMILES string of C([C@H]1[C@@H]([C@H](C(=O)O1)O)O)O.

A) enantiomers

B) diastereomers

C) constitutional isomers

D) identical

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

72) Which structure is the enantiomer of the following compound?

The bond-line structure of the compound has a SMILES string of C[C@H](C(C)C)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

73) Which structure is the enantiomer of the following compound?

The bond-line structure of the compound has a three-carbon chain, in which C 1 and C 3 are each bonded to a hydroxyl group, and C 2 is wedge bonded to the third hydroxyl group.

A) I

B) II

C) III

D) IV

E) None is possible

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

74) Which structure is the enantiomer of the following compound?

The bond-line structure of the compound has a SMILES string of C1[C@@H]([C@H](C(=O)O1)O)O.

A) I

B) II

C) III

D) IV

E) No enantiomers are possible.

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

75) Which structure is a diastereomer of the following compound?

The bond-line structure of the compound has a SMILES string of C1[C@@H]([C@H](C(=O)O1)O)O.

A) I only

B) II only

C) III only

D) I and II

E) III and IV

Diff: 3

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

76) Which compound is a diastereomer of the structure shown?

The bond-line structure of the compound has a SMILES string of C[C@H](C(C)C)O.

A) I

B) II

C) III

D) IV

E) There are no diastereomers.

Diff: 3

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

77) Which structure is a diastereomer of the following compound?

The bond-line structure of the compound has a SMILES string of CC1=CC=C[C@@H]([C@@H]1O)O.

$Four bond-line structures represent four different compounds. The first compound has a SMILES string of O[C@@H]1C(=C/C=C\[C@H]1O)\C. The second compound has a cyclohexane ring, in which C 1 and C 2 are each dash bonded to a hydroxyl group, C 3 is bonded to a methyl group and double bonded to C 4, and C 5 is double bonded to C 6. The third compound has a SMILES string of O[C@H]1C(=C/C=C\[C@@H]1O)\C. The fourth compound has a similar structure to the second compound, except that the single bond at C 3 is replaced with a dash bond.$

A) I only

B) II only

C) III only

D) I and II

E) I and III

Diff: 3

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

78) How many stereoisomers are there for the compound shown?

The bond-line structure of the compound has a cyclopentane ring, in which C 1 is double bonded to an oxygen atom, and C 2 and C 3 are each bonded to a hydroxyl group.

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 3

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

79) How many stereoisomers are there for the compound shown?

The bond-line structure of the compound has a SMILES string of CC(C(c1ccccc1)O)NC.

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 3

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

80) Which of the following choices is a diastereomer of the first structure shown?

The bond-line structure of the compound has a SMILES string of C[C@H]([C@@H](c1ccccc1)O)NC.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

81) Which of the following choices is a diastereomer of the first structure shown.

The bond-line structure of the compound has a SMILES string of CC[C@H]1[C@@H](CCC1=O)C=C.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

82) Which of the following choices is a diastereomer of the first structure shown?

The bond-line structure of the compound has a four-carbon chain, in which C 2 and C 3 are each wedge bonded to a chlorine atom.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have

83) Is the following a meso compound?

The bond-line structure of the compound has a four-carbon chain, in which C 2 and C 3 are each wedge bonded to a chlorine atom.

A) Yes, because it cannot be superimposed with mirror image compounds.

B) Yes, because it cannot be superimposed with similar compounds that are not mirror images.

C) Yes, because it has rotational symmetry.

D) No, because it has a mirror image.

E) No, because it has two chiral centers.

Diff: 2

Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral

84) Which of the following can exist as a meso isomer?

Four bond-line structures represent four different compounds. The first structure has a SMILES string of CC(C(C)Cl)Cl. The second structure has a SMILES string of CC(C(C)Br)Cl. The third structure has a SMILES string of CC(C)C(C)Br. The fourth compound has a SMILES string of CC(C)C(C)C.

A) I

B) II

C) III

D) IV

Diff: 2

85) Does the following contain a plane of symmetry?

The bond-line structure of the compound has a cyclohexane ring, in which C 1 is wedge bonded to a methyl group.

A) Yes, because it can be divided into two halves that would look identical if reflected in a mirror.

B) Yes, because it has at least one chiral center and that is required for a plane of symmetry to exist.

C) Yes, because it contains a ring.

D) No, because it is achiral.

E) No, because it has a mirror image.

Diff: 1

86) Which of the choices correctly illustrates a plane of symmetry in the compound shown?

The bond-line structure of the compound has a cyclohexane ring, in which C 1 and C 3 are each wedge bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) There are no planes of symmetry present.

Diff: 1

87) Draw in the plane of symmetry in the following compound.

The bond-line structure of the compound has a SMILES string of CC[C@@H](C)[C@H](C)CC.

A) I

B) II

C) III

D) IV

E) There are no planes of symmetry present.

Diff: 3

88) What is the total number of stereoisomers of this compound?

The bond-line structure of the compound has a SMILES string of CC1CC(C(CC1C)C)C.

A) 1

B) 2

C) 4

D) 7

E) None

Diff: 3

89) How many stereoisomers are possible for 2,3-dimethylbutane?

A) 1

B) 2

C) 4

D) 7

E) None

Diff: 3

90) How many stereoisomers are possible for 1,3,5-trimethylcyclohexane.

A) 1

B) 2

C) 4

D) 7

E) None

Diff: 2

91) Draw the meso isomer of the following compound.

An illustration shows a compound and four possible structures for a meso isomer, labeled 1 through 4 (in Roman Numerals).
The compound has a 6-carbon chain. C 3 and C 4 are each bonded to a chlorine atom.

A) I

B) II

C) III

D) IV

E) No meso isomer exists.

Diff: 3

92) Draw the meso isomer of the following compound.

An illustration shows a compound and four possible structures for a meso isomer, labeled 1 through 4 (in Roman Numerals).
The compound has a 2-carbon chain. C 1 and C 2 are each bonded to a hydroxyl group and a C O 2 M e group.

A) I

B) II

C) III

D) IV

E) No meso isomer exists.

Diff: 3

93) Draw the meso isomer of the following compound.

A) I

B) II

C) III

D) IV

E) No meso isomer exists.

Diff: 2

94) How many possible stereoisomers are there for Crestor® (rosuvastatin), a medication used to reduce cholesterol?

The structure of rosuvastatin has a SMILES string of CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)/C=C/[C@H](C[C@H](CC(=O)O)O)O.

A) 2

B) 4

C) 6

D) 8

Diff: 3

95) Which of the following choices represents the Fischer projection of the compound shown?

An illustration shows a compound and five Fischer projections, labeled 1 through 5.
The compound has a 4-carbon chain. C 2 and C 3 are each wedge bonded to a bromine atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

96) Which of the following choices represents the Fischer projection of the compound shown?

An illustration shows a compound and five Fischer projections labeled 1 through 5 (in Roman Numerals).
The compound has a 2-carbon chain. C 1 and C 2 are each dash bonded to a hydroxyl group and single bonded to a C O 2 M e group.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

97) Which of the following choices represents the Fischer projection of the compound shown?

The bond-line structure of the compound has a six-carbon chain, in which C 2 and C 4 are each dash bonded to a hydroxyl group, and C 3 and C 5 are each wedge bonded to a hydroxyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

98) Which of the following choices represents the Fischer projection of the compound shown?

An illustration shows a compound and five Fischer projections labeled 1 through 5 (in Roman Numerals).
The compound has a 6-carbon chain. C 2, C 3, and C 4 are each wedge bonded to a hydroxyl group. C 5 is dash bonded to a hydroxyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

99) Which of the following choices represents the wedge/dash drawing of the Fischer projection shown?

The Fischer projection of the compound has a four-carbon vertical chain, in which C 1 and C 4 are methyl groups, C 2 is bonded to a hydrogen atom on the left and a hydroxyl group on the right, and C 3 is bonded to a hydroxyl group on the left and a hydrogen atom on the right.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

100) Which of the following choices represents the wedge/dash drawing of the Fischer projection shown?

The Fischer projection of the compound has a five-carbon vertical chain, in which C 1 and C 4 are methyl groups, C 2 and C 3 are each bonded to a hydroxyl group on the left and a hydrogen atom on the right, and C 4 is bonded to a hydrogen atom on the left and a hydroxyl group on the right.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

101) Which of the following choices represents the wedge/dash drawing of the Fischer projection shown?

The Fischer projection of the compound has a six-carbon vertical chain, in which C 1 and C 4 are methyl groups, C 2, C 3, and C 4 are each bonded to a hydroxyl group on the left and a hydrogen atom on the right, and C 5 is bonded to a hydrogen atom on the left and a hydroxyl group on the right.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

102) Which of the following choices represents the wedge/dash drawing of the Fischer projection shown?

The Fischer projection of the compound has a four-carbon vertical chain, in which C 1 and C 4 are methyl groups, and C 2 and C 3 are each bonded to a hydroxyl group on the left and a hydrogen atom on the right.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

103) Which of the following is a correct Fischer projection of the following compound?

The bond-line structure of the compound has a four-carbon chain, in which C 2 and C 3 are each wedge bonded to a bromine atom.

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

104) Which of the following is a correct Fischer projection of the following compound?

The bond-line structure of the compound has a SMILES string of CC[C@@H]([C@@H](C)Br)Br.

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

105) Which of the following is a correct Fischer projection of the following compound?

The bond-line structure of the compound has a six-carbon chain, in which C 2 is wedge bonded to a hydroxyl group, and C 3, C 4, and C 5 are each dash bonded to a hydroxyl group.

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

106) Which of the following structures is the correct wedge/dash drawing of the following Fischer projection?

The Fischer projection of the compound has a four-carbon vertical chain, in which C 1 is an ethyl group, C 2 is bonded to a hydrogen atom on the left and a bromine atom on the right, C 3 is bonded to a bromine atom on the left and a hydrogen atom on the right, and C 4 is a methyl group.

Four bond-line structures represent four different compounds. The first compound has a SMILES string of CC[C@@H]([C@@H](C)Br)Br. The second compound has a five-carbon chain, in which C 2 and C 3 are each wedge bonded to a bromine atom. The third compound has a SMILES string of CC[C@H]([C@@H](C)Br)Br. The fourth compound is the same as that of the third compound.

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

107) Which of the following structures is a correct wedge/dash drawing of the following Fischer projection?

The Fischer projection of the compound has a six-carbon vertical chain, in which C 1 and C 6 are methyl groups, C 2, C 3, C 4 and C 5 are each bonded to a hydrogen atom on the left and a hydroxyl group on the right.

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

108) What is the relationship between the following structures?

A) enantiomers

B) diastereomers

C) identical

D) constitutional Isomers

Diff: 1

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

109) What is the relationship between the following structures?

A) enantiomers

B) diastereomers

C) identical

D) constitutional Isomers

Diff: 1

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

110) What is the relationship between the following structures?

A) enantiomers

B) diastereomers

C) identical

D) constitutional Isomers

Diff: 2

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

111) Assign the following stereocenter as having the R or S absolute configuration.

The Fischer projection of the compound has a two-carbon vertical chain, in which C 1 is bonded to a hydrogen atom on the left, a hydroxyl group at the top, and an ethyl group on the right, and C 2 is a methyl group.

A) S

B) R

C) S and R

D) Neither S nor R

Diff: 2

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

112) Assign the following stereocenter as having the R or S absolute configuration.

The Fischer projection of the compound has a four-carbon vertical chain, in which C 1 and C 4 are methyl groups, C 2 is bonded to a hydrogen atom on the left and a methyl group on the right, and C 3 is bonded to a hydroxyl group on the left and a hydrogen atom on the right.

A) S

B) R

C) S and R

D) Neither S nor R

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

113) Assign the following stereocenter as having the R or S absolute configuration.

The Fischer projection of the compound has a four-carbon vertical chain, in which C 1 is an ethyl group, C 2 is bonded to a hydrogen atom on the left and a bromine atom on the right, C 3 is bonded to a hydroxyl group on the left and on the right, and C 4 is a methyl group.

A) S

B) R

C) S and R

D) Neither S nor R

Diff: 2

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

114) Provide an IUPAC name for the following compound.

The Fischer projection of the compound has a four-carbon vertical chain, in which C 1 and C 4 are methyl group, C 2 is bonded to a hydrogen atom on the left and on the right, and C 3 is bonded to a hydrogen atom on the left and a hydroxyl group on the right.

A) (R)-2-butanol

B) (R)-2-propanol

C) (S)-3-butanol

D) (R)-3-butanol

E) (S)-2-butanol

Diff: 2

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

115) Which of the following is the IUPAC name for the following compound?

The Fischer projection of the compound has a five-carbon vertical chain, in which C 1 and C 4 are methyl group, C 2 and C 3 are each bonded to a hydrogen atom on the left and on the right, and C 4 is bonded to a hydrogen atom on the left and a hydroxyl group on the right.

A) (S)-2-pentanol

B) (S)-2-butanol

C) (R)-2-pentanol

D) (R)-2-butanol

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

116) Identify the relationship between these two structures.

A) diastereomers

B) enantiomers

C) identical

D) unrelated compounds

Diff: 3

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar

117) What is the relationship between the two structures shown?

A) identical

B) enantiomers

C) diastereomers

D) none of these

Diff: 3

Learning Objective: 5.8 Describe conformationally mobile systems

118) What is the relationship between the two structures shown?

A) same compound

B) enantiomers

C) diastereomers

D) none of these

Diff: 3

Learning Objective: 5.8 Describe conformationally mobile systems

119) What is the relationship between the two structures shown?

A) same compound

B) enantiomers

C) diastereomers

D) none of these

Diff: 3

Learning Objective: 5.8 Describe conformationally mobile systems

120) What is the relationship between the two structures shown?

A) same compound

B) enantiomers

C) diastereomers

D) none of these

Diff: 3

Learning Objective: 5.8 Describe conformationally mobile systems

121) What is the relationship between the two structures shown?

A) same compound

B) enantiomers

C) diastereomers

D) none of these

Diff: 3

Learning Objective: 5.8 Describe conformationally mobile systems

122) Stereoisomers that result from the hindered rotation of a single bond are called ___________.

A) constrained diastereomers

B) atropisomers

C) enantiomers

D) diastereomers

E) constitutional isomers

Diff: 2

Learning Objective: 5.9 Discuss ways in which a compound can be chiral without containing a chiral center

123) What is the relationship between the two structures shown?

A) same compound

B) enantiomers

C) diastereomers

D) none of these

Diff: 2

Learning Objective: 5.9 Discuss ways in which a compound can be chiral without containing a chiral center

124) Identify the hybridization of the central carbon of an allene.

A) sp

B) sp2

C) sp3

D) sp4

Diff: 2

Learning Objective: 5.9 Discuss ways in which a compound can be chiral without containing a chiral center

125) Which of the following strategies will not be an effective way to separate enantiomers?

A) chiral chromatography

B) distillation

C) crystallization

D) chiral resolving agents

Diff: 2

Learning Objective: 5.10 Describe resolution and methods to separate enantiomers

126) When a racemic mixture is reacted with a single enantiomer of another compound, then a pair of ________ is formed.

A) identical compounds

B) enantiomers

C) diastereomers

D) none of the above

Diff: 2

Learning Objective: 5.10 Describe resolution and methods to separate enantiomers

127) In chiral column chromatography, ________ adsorbent is used to separate a pair of enantiomers.

A) an achiral

B) a polar

C) a nonpolar

D) a chiral

Diff: 2

Learning Objective: 5.10 Describe resolution and methods to separate enantiomers

128) Is the following alkene E, Z, or neither?

The bond-line structure of the compound has a SMILES string of C/C=C/OC.

A) E

B) Z

C) Neither

D) It is one or the other, but which is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

129) Is the following alkene E, Z, or neither?

The bond-line structure of the compound has a SMILES string of CC=C(F)C.

A) E

B) Z

C) Neither

D) It is one or the other, but which is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

130) Is the following alkene E, Z, or neither?

The bond-line structure of the compound has a SMILES string of C/C=C/C.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

131) Is the following alkene E, Z, or neither?

The bond-line structure of the compound has a SMILES string of C1CCC=CC1.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

132) Is the following alkene E, Z, or neither?

$The bond-line structure of the compound has a SMILES string of O1\C(OCCC1)=C/C.$

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

133) Is the following alkene E, Z, or neither?

The structure of an alkene has two carbon atoms double bonded to each other, in which C 1 is bonded to a hydrogen atom and a methyl group, and C 2 is bonded to a methyl group and a fluorine atom.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

134) Is the following alkene E, Z, or neither?

The structure of an alkene has two carbon atoms double bonded to each other, in which C 1 is bonded to a bromine atom and a methyl group, and C 2 is bonded to a methyl group and a fluorine atom.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

135) Is the following alkene E, Z, or neither?

The structure of an alkene has two carbon atoms double bonded to each other, in which C 1 is bonded to CH 3 C H 2 group and a hydrogen atom, and C 2 is bonded to a methyl group and a fluorine atom.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

136) Is the following alkene E, Z, or neither?

The structure of an alkene has two carbon atoms double bonded to each other, in which C 1 is bonded to a methyl group and a chlorine atom, and C 2 is bonded to a methyl group and a fluorine atom.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

137) Is the indicated alkene in Crestor® (rosuvastatin), a medication used to reduce cholesterol, classified as E, Z, or neither?

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

138) Is the alkene found in Singulair® (montelukast), a medication used to manage asthma, classified as E, Z, or neither?

The structure of montelukast has a SMILES string of CC(C)(c1ccccc1CC[C@H](c2cccc(c2)/C=C/c3ccc4ccc(cc4n3)Cl)SCC5(CC5)CC(=O)O)O.

A) E

B) Z

C) Neither

D) It is impossible to determine from the information given.

Diff: 2

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

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Chapter 5 Stereoisomerism

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