Organic Chemistry 5th Edition by Smith - Test Bank

Organic Chemistry 5th Edition by Smith – Test Bank

 

Instant Download – Complete Test Bank With Answers

 

 

Sample Questions Are Posted Below

 

1. What is the main carbohydrate in the seeds and roots of plants?

 

1. Starch

 

1. Glucose

 

1. Cellulose

 

1. Glycogen

 

Accessibility: Keyboard Navigation

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.01

 

Subtopic: Chiral vs achiral molecules

 

Topic: Stereochemistry

 

2. Which of the following statements about starch and cellulose is true?

 

1. Starch and cellulose are not stereoisomers.

 

1. In cellulose, the O atom joins two rings using one equatorial and one axial bond.

 

1. In starch, the O atom joins two rings using two equatorial bonds.

 

1. In cellulose, the O atom joins two rings using two equatorial bonds.

 

Accessibility: Keyboard Navigation

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.01

 

Subtopic: Chiral vs achiral molecules

 

Topic: Stereochemistry

 

3. Which of the following statements about constitutional isomers if not true?

 

1. They have different IUPAC names.

 

1. They always have the same functional groups.

 

1. They have different physical properties.

 

1. They have different chemical properties.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

4. Which of the following statements about stereoisomers is not true?

 

1. Stereoisomers have identical IUPAC names except for a prefix like cis or trans.

 

1. Stereoisomers differ in configuration.

 

1. Stereoisomers always have the same functional groups.

 

1. Stereoisomers differ only in their structural formula.

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

5.

 

What is the relationship between the following two compounds?

 

 

 

 

 

 

 

 

 

 

1. Stereoisomers

 

1. Constitutional isomers

 

1. Identical

 

1. Not isomers, different compounds

 

 

 

 

 

 

 

 

 

 

6.

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

What is the relationship between the following two compounds?

 

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Identical

 

1. Stereoisomers

 

1. Not isomers, different compounds

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

7.

 

What is the relationship between the following two compounds?

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Identical

 

1. Stereoisomers

 

1. Not isomers, different compounds

 

 

 

 

 

 

 

 

 

 

8.

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

What is the relationship between the following two compounds?

 

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Stereoisomers

 

1. Identical

 

1. Not isomers, different compounds

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

9. Which of the following is the definition of chirality?

 

1. The existence of a molecule with a mirror image.

 

1. The existence of a molecule with a carbon atom that has four different substituents.

 

1. The existence of a molecule that is superimposable on its mirror image.

 

1. The existence of a molecule that is not superimposable on its mirror image.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Topic: Stereochemistry

 

10. Which of the following statements is not true?

 

1. A molecule that is superimposable on its mirror image is said to achiral.

 

1. A molecule that is not superimposable on its mirror image is said to be chiral.

 

1. A molecule that is superimposable on its mirror image is said to be chiral.

 

1. A carbon atom bonded to four different groups is a stereogenic center.

 

 

 

 

 

 

 

 

 

 

11. Which of the following statements is true?

 

1. Enantiomers are mirror images that are not superimposable.

 

1. A molecule that is superimposable on its mirror image is chiral.

 

1. A chiral molecule usually contains a plane of symmetry.

 

1. An achiral molecule does not contain a plane of symmetry.

 

 

 

 

 

 

 

 

 

 

12. Which of the following statements is true?

 

1. Achiral molecules usually contain a plane of symmetry.

 

1. With one tetrahedral stereogenic center, a molecule may or may not be chiral.

 

1. With two or more stereogenic centers, a molecule is always chiral.

 

1. Chiral molecules usually contain a plane of symmetry.

 

 

 

 

 

 

 

 

Accessibility: Keyboard Navigation Bloom’s Level: 2. Understand  Difficulty: Easy Gradable: automatic Section: 05.03

 

Subtopic: Chiral vs achiral molecules Topic: Stereochemistry

 

 

 

 

 

 

 

 

 

Accessibility: Keyboard Navigation Bloom’s Level: 2. Understand  Difficulty: Easy Gradable: automatic Section: 05.03

 

Subtopic: Chiral vs achiral molecules Topic: Stereochemistry

 

 

 

 

 

 

 

 

 

Accessibility: Keyboard Navigation Bloom’s Level: 2. Understand  Difficulty: Easy Gradable: automatic Section: 05.03

 

Subtopic: Chiral vs achiral molecules Subtopic: Stereogenic/chirality carbon centers Topic: Stereochemistry

 

13. Which of the following is the correct definition for a pair of enantiomers?

 

1. A pair of stereoisomers that have a plane of symmetry.

 

1. A pair of stereoisomers that are not mirror images of each other.

 

1. A pair of stereoisomers that are not superimposable mirror images of each other.

 

1. A pair of stereoisomers that are superimposable mirror images of each other.

 

 

 

 

 

 

 

 

 

 

 

 

 

14.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

Which of the following molecules has a plane of symmetry?

 

 

 

 

 

 

 

 

 

 

1. I

 

1. II

 

1. III

 

1. IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

15. Which of the following statements is true?

 

1. The presence of a plane of symmetry makes a molecule chiral.

 

1. An achiral molecule must have one or more stereogenic centers.

 

1. All molecules that have stereogenic centers are chiral.

 

1. Stereoisomers that are not superimposable on their mirror image are enantiomers.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

16. Which of the following molecules are chiral?

 

1. cis-1,3-Dibromocyclohexane

 

II.1-Bromo-1-methylcyclohexane

 

III.trans-1-Bromo-3-methylcyclohexane

 

IV.cis-1-Bromo-3-methylcyclohexane

 

1. I, II

 

1. II, III

 

1. I, IV

 

1. III, IV

 

 

 

 

 

 

 

 

 

 

17. Which of the following molecules are chiral?

 

I.2-Chlorobutane II.3-Bromopentane III.1-Bromo-2-methylpropene IV.2-Bromo-3-methylbutane

 

1. I, II

 

1. I, IV

 

1. II, III

 

1. III, IV

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Accessibility: Keyboard Navigation Bloom’s Level: 2. Understand  Difficulty: Easy Gradable: automatic Section: 05.03

 

Subtopic: Chiral vs achiral molecules Subtopic: Stereogenic/chirality carbon centers Topic: Stereochemistry

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Accessibility: Keyboard Navigation Bloom’s Level: 2. Understand  Difficulty: Easy Gradable: automatic Section: 05.03

 

Subtopic: Chiral vs achiral molecules Subtopic: Stereogenic/chirality carbon centers Topic: Stereochemistry

 

18. Which of the following molecules are achiral?

 

 

 

 

 

 

 

 

 

 

 

 

1. II, III

 

1. I, II

 

1. I, IV

 

1. III, IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

19. Which of the following molecules are chiral?

 

 

 

 

 

 

 

 

 

 

 

 

1. II, III

 

1. I, II

 

1. I, IV

 

1. III, IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

20. How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?

 

 

 

 

 

 

 

 

 

 

 

1. 0

 

1. 1

 

1. 2

 

1. 3

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

21. How many stereogenic centers are present in the following compound?

 

 

 

 

 

 

 

 

 

1. 0

 

1. 1

 

1. 2

 

1. 3

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

22. How many stereogenic centers are present in fructose, a simple sugar?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

23. How many stereogenic centers are present in the following compound?

 

 

 

 

 

 

 

 

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

24. How many stereogenic centers are present in menthol?

 

 

 

 

 

 

 

 

 

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

25. How many stereogenic centers are present in the following compound?

 

 

 

 

 

 

 

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

26. How many stereogenic centers are present in the following molecule?

 

 

 

 

 

 

 

 

1. 1

 

1. 2

 

1. 4

 

1. 5

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

27. How many stereoisomers are possible for a molecule with formula CH₃CHBrCH(OH)CH₃?

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

28. How many stereoisomers can be drawn for a molecule with formula CH₃CH(OH)CH(OH)CH₃?

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

29. What is the total number of possible stereoisomers for the following molecule?

 

 

 

 

 

 

 

 

1. 2

 

1. 4

 

1. 6

 

1. 8

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

30. How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane?

 

1. 2

 

1. 3

 

1. 4

 

1. 6

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

31. How many chiral stereoisomers can be drawn for dimethycyclopropane?

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

 

 

 

 

 

 

 

 

1. 0

 

1. 1

 

1. 2

 

1. 3

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

33. How many stereogenic centers are present in the following compound?

 

 

 

 

 

 

 

 

 

 

1. 0

 

1. 1

 

1. 2

 

1. 3

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Chiral vs achiral molecules

 

Subtopic: Stereogenic/chirality carbon centers

 

Topic: Stereochemistry

 

34.

 

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

 

 

 

 

 

 

 

 

 

1. III > I > II > IV

 

1. I > II > IV > III

 

1. III > II > IV > I

 

1. III > IV > II > I

 

 

 

 

 

 

 

 

 

 

35.

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

 

 

 

 

 

 

 

 

 

1. I > II > III > IV

 

1. II > I > IV > III

 

1. II > I > III > IV

 

1. I > II > IV > III

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

36.

 

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

 

 

 

 

 

 

 

 

 

1. I > III > IV > II

 

1. III > IV > I > II

 

1. IV > III > I > II

 

1. IV > I > III > II

 

 

 

 

 

 

 

 

 

 

37.

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

 

 

 

 

 

 

 

 

 

1. I > II > IV > III

 

1. IV > II > I > III

 

1. IV > I > II > III

 

1. III > II > I> IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

38.

 

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.

 

 

 

 

 

 

 

 

 

 

1. IV > III > I > II

 

1. IV > I > III > II

 

1. III > IV > I > II

 

1. II > I > III > IV

 

 

 

 

 

 

 

 

 

 

39.

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

Which of the following compounds has a plane of symmetry?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. I and II

 

1. II and III

C.

II, III, and IV

 

 

1. III and IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

40. Which of the following structures has a different configuration from the other three?

 

 

 

 

 

 

 

 

 

 

 

 

 

1. I

 

1. II

 

1. III

 

1. IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

41. Which of the following structures has a different configuration from the other three?

 

 

 

 

 

 

 

 

 

 

1. I

 

1. II

 

1. III

 

1. IV

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

42. Which of the following structures has the S configuration?

 

 

 

 

 

 

 

 

 

 

 

 

1. Only I

 

1. Only II

 

1. Only I and II

 

D.

 

I, II, and III

 

 

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

43. Which of the following structures has the R configuration?

 

 

 

 

 

 

 

 

 

 

 

 

 

1. Only I

 

1. Only II

 

1. Only I and II

D.

I, II, and III

 

 

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

44.

 

Which of the following structures has the R configuration?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. Only I

 

1. Only II

 

1. Only I and II

D.

I, II, and III

 

 

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: R and S nomenclature

 

Topic: Stereochemistry

 

45. Which of the following is the definition for a pair of diastereomers?

 

A.

A pair of stereoisomers with stereogenic centers but is not chiral.

 

 

1. A pair of stereoisomers that are superimposable mirror images of each other.

 

1. A pair of stereoisomers that are not superimposable mirror images of each other.

 

1. A pair of stereoisomers that are not mirror images of each other.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

46. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

47. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

48. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

49. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

50. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

51. What is the relationship between the following compounds?

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

52. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

53. What is the relationship between the following compounds?

 

 

 

 

 

 

 

 

1. Constitutional isomers

 

1. Diastereomers

 

1. Enantiomers

 

1. Identical

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

54. Which of the following statements about meso compounds is not true?

 

1. A meso compound generally has a plane of symmetry.

 

1. A meso compound and its mirror image are identical.

 

1. A meso compound is achiral.

 

1. A meso compound is chiral.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

55. Which of the following compounds is a meso compound?

 

1. (2R, 3S)-dichlorobutane

 

1. (2R, 3R)-dichlorobutane

 

1. (2R, 3S)-3-chloro-2-butanol

 

1. (2R, 3R)-3-chloro-2-butanol

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: R and S nomenclature

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

56. Which of the following compounds are meso?

 

 

 

 

 

 

 

 

 

 

1. Only I

 

1. Only II

 

1. I and II

 

1. Neither

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: R and S nomenclature

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

57. Which of the following compounds can have a meso stereoisomer?

 

 

 

 

 

 

 

 

 

 

1. I

 

1. II

 

1. III

 

1. IV

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: R and S nomenclature

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

58. How many stereoisomers of 1,3-dibromocyclopentane exist?

 

1. 1

 

1. 2

 

1. 3

 

1. 4

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.10

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

59. Which of the following compounds does not have a plane of symmetry?

 

 

 

 

 

 

 

 

 

 

1. Only I and II

 

1. Only II

 

1. Only III and IV

D.

Only I, II, and IV

 

 

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

60. Which of the following cyclic molecules is a meso compound?

 

 

 

 

 

 

 

 

 

 

1. I

 

1. II

 

1. III

 

1. IV

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

61. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?

 

1. 3

 

1. 4

 

1. 5

 

1. 6

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 4. Analyze

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.10

 

Subtopic: Stereogenic/chirality carbon centers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

62. A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H₂ What is the specific rotation of this compound?

 

1. -10°

 

1. +100°

 

1. +10°

 

1. -100°

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

63. A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer?

 

1. +50°

 

1. -40°

 

1. +40°

 

1. -50°

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

64. How much of the R enantiomer is present in 10 g of a mixture that has an enantiomeric excess of 30% of the S isomer?

 

 

 

3. 0 g

 

3. 5 g

 

6. 5 g

 

7. 0 g

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

 

65. A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?

 

 

 

5. +5.6°

 

11. +11.2°

 

2. +2.8°

 

1. +1.4°

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

66. What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other?

 

1. 70

 

1. 85

 

1. 40

 

1. 30

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

67. If a mixture has an ee of 90%, what is the percentage of each enantiomer?

 

1. 65% : 35%

 

1. 55% : 45%

 

1. 80% : 20%

 

1. 95% : 5%

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

68. A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture?

 

1. 75

 

1. 40

 

1. 65

 

1. 50

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.12

 

Subtopic: Optical activity

 

Subtopic: Physical properties of stereoisomers

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry

 

69.

 

 

 

 

 

 

 

 

 

 

 

 

A.

 

Which of the following compounds are chiral?

 

 

I and II

 

 

B.

 

II and III

 

 

C.

 

III and IV

 

 

D.

I and IV

 

 

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: Chiral vs achiral molecules

 

Topic: Stereochemistry

 

70.

 

 

 

 

 

 

 

 

 

 

 

A.

 

Which of the following compounds is identical to compound A?

 

 

I and II

 

 

B.

 

II and III

 

 

C.

 

I and III

 

 

1. II

 

Bloom’s Level: 3. Apply

 

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.11

 

Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

 

Topic: Stereochemistry