Question 1

Which of the following compounds is a meso compound?

Accepted Answer

A) (2R, 3S)-dichlorobutane 
B) (2R, 3R)-dichlorobutane 
C) (2R, 3S)-3-chloro-2-butanol 
D) (2R, 3R)-3-chloro-2-butanol 
A) (2R, 3S)-dichlorobutane 
B) (2R, 3R)-dichlorobutane 
C) (2R, 3S)-3-chloro-2-butanol 
D) (2R, 3R)-3-chloro-2-butanol

Question 2

Which of the following compounds are meso?

Accepted Answer

A) Only I 
B) Only II 
C) I and II 
D) Neither 
A) Only I 
B) Only II 
C) I and II 
D) Neither

Question 3

Which of the following is the definition of chirality?

Accepted Answer

A) The existence of a molecule with a mirror image. 
B) The existence of a molecule with a carbon atom that has four different substituents. 
C) The existence of a molecule that is superimposable on its mirror image. 
D) The existence of a molecule that is not superimposable on its mirror image. 
A) The existence of a molecule with a mirror image. 
B) The existence of a molecule with a carbon atom that has four different substituents. 
C) The existence of a molecule that is superimposable on its mirror image. 
D) The existence of a molecule that is not superimposable on its mirror image.

Question 4

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

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
A) 1 
B) 2 
C) 3 
D) 4

Question 5

What is the relationship between the following compounds?

Accepted Answer

A) Constitutional isomers 
B) Diastereomers 
C) Enantiomers 
D) Identical 
A) Constitutional isomers 
B) Diastereomers 
C) Enantiomers 
D) Identical

Question 6

Which of the following structures has the S configuration?

Accepted Answer

A) Only I 
B) Only II 
C) Only I and II 
D) I, II, and III 
A) Only I 
B) Only II 
C) Only I and II 
D) I, II, and III

Question 7

How many stereogenic centers are present in the following compound?

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
A) 0 
B) 1 
C) 2 
D) 3

Question 8

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

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
A) 0 
B) 1 
C) 2 
D) 3

Question 9

How many chiral stereoisomers can be drawn for dimethycyclopropane?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
A) 1 
B) 2 
C) 3 
D) 4

Question 10

How many stereogenic centers are present in the following compound?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
A) 1 
B) 2 
C) 3 
D) 4

Question 11

Which of the following molecules are chiral?

Accepted Answer

A) II, III 
B) I, II 
C) I, IV 
D) III, IV 
A) II, III 
B) I, II 
C) I, IV 
D) III, IV

Question 12

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

Accepted Answer

A) They have different IUPAC names. 
B) They always have the same functional groups. 
C) They have different physical properties. 
D) They have different chemical properties. 
A) They have different IUPAC names. 
B) They always have the same functional groups. 
C) They have different physical properties. 
D) They have different chemical properties.

Question 13

What is the relationship between the following two compounds?

Accepted Answer

A) Constitutional isomers 
B) Identical 
C) Stereoisomers 
D) Not isomers, different compounds 
A) Constitutional isomers 
B) Identical 
C) Stereoisomers 
D) Not isomers, different compounds

Question 14

What is the relationship between the following two compounds?

Accepted Answer

A) Stereoisomers 
B) Constitutional isomers 
C) Identical 
D) Not isomers, different compounds 
A) Stereoisomers 
B) Constitutional isomers 
C) Identical 
D) Not isomers, different compounds

Question 15

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

Accepted Answer

A) 65% : 35% 
B) 55% : 45% 
C) 80% : 20% 
D) 95% : 5% 
A) 65% : 35% 
B) 55% : 45% 
C) 80% : 20% 
D) 95% : 5%

Question 16

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 17

What is the relationship between the following compounds?

Accepted Answer

A) Constitutional isomers 
B) Diastereomers 
C) Enantiomers 
D) Identical 
A) Constitutional isomers 
B) Diastereomers 
C) Enantiomers 
D) Identical

Question 18

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?

Accepted Answer

A) +5.6° 
B) +11.2° 
C) +2.8° 
D) +1.4° 
A) +5.6° 
B) +11.2° 
C) +2.8° 
D) +1.4°

Question 19

What is the relationship between the following compounds?

Accepted Answer

A) Constitutional isomers 
B) Diastereomers 
C) Enantiomers 
D) Identical 
A) Constitutional isomers 
B) Diastereomers 
C) Enantiomers 
D) Identical

Question 20

Which of the following structures has the R configuration?

Accepted Answer

A) Only I 
B) Only II 
C) Only I and II 
D) I, II, and III 
A) Only I 
B) Only II 
C) Only I and II 
D) I, II, and III

Exam 5: Stereochemistry

Which of the following compounds is a meso compound?

Which of the following compounds are meso?

Which of the following is the definition of chirality?

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

What is the relationship between the following compounds?

Which of the following structures has the S configuration?

How many stereogenic centers are present in the following compound?

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

How many chiral stereoisomers can be drawn for dimethycyclopropane?

How many stereogenic centers are present in the following compound?

Which of the following molecules are chiral?

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

What is the relationship between the following two compounds?

What is the relationship between the following two compounds?

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

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

What is the relationship between the following compounds?

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?

What is the relationship between the following compounds?

Which of the following structures has the R configuration?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers, and Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Filters

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