Question 1

Which of the following compounds has a plane of symmetry?

Accepted Answer

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

Question 2

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 3

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 4

Give the IUPAC name for the following compound:

Accepted Answer

A) (1R,3R)-1-ethyl-3-methylcyclohexane 
B) (1R,3S)-1-ethyl-3-methylcyclohexane 
C) (1S,3R)-1-ethyl-3-methylcyclohexane 
D) (1S,3S)-1-ethyl-3-methylcyclohexane 
A) (1R,3R)-1-ethyl-3-methylcyclohexane 
B) (1R,3S)-1-ethyl-3-methylcyclohexane 
C) (1S,3R)-1-ethyl-3-methylcyclohexane 
D) (1S,3S)-1-ethyl-3-methylcyclohexane

Question 5

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

Accepted Answer

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

Question 6

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 7

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 8

Which of the following statements is not true?

Accepted Answer

A) A molecule that is superimposable on its mirror image is said to achiral. 
B) A molecule that is not superimposable on its mirror image is said to be chiral. 
C) A molecule that is superimposable on its mirror image is said to be chiral. 
D) A carbon atom bonded to four different groups is a stereogenic center. 
A) A molecule that is superimposable on its mirror image is said to achiral. 
B) A molecule that is not superimposable on its mirror image is said to be chiral. 
C) A molecule that is superimposable on its mirror image is said to be chiral. 
D) A carbon atom bonded to four different groups is a stereogenic center.

Question 9

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 10

Which of the following compounds are chiral?

Accepted Answer

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

Question 11

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

Accepted Answer

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

Question 12

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

Accepted Answer

A) 2 
B) 4 
C) 6 
D) 8 
A) 2 
B) 4 
C) 6 
D) 8

Question 13

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

Accepted Answer

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

Question 14

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

Accepted Answer

A) A pair of stereoisomers with stereogenic centers but is not chiral. 
B) A pair of stereoisomers that are superimposable mirror images of each other. 
C) A pair of stereoisomers that are not superimposable mirror images of each other. 
D) A pair of stereoisomers that are not mirror images of each other. 
A) A pair of stereoisomers with stereogenic centers but is not chiral. 
B) A pair of stereoisomers that are superimposable mirror images of each other. 
C) A pair of stereoisomers that are not superimposable mirror images of each other. 
D) A pair of stereoisomers that are not mirror images of each other.

Question 15

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

Accepted Answer

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

Question 16

Give the IUPAC name for the following compound:

Accepted Answer

A) (1R,2R)-1,2-dimethylcyclopentane 
B) (1R,2S)-1,2-dimethylcyclopentane 
C) (1S,2R)-1,2-dimethylcyclopentane 
D) (1S,2S)-1,2-dimethylcyclopentane 
A) (1R,2R)-1,2-dimethylcyclopentane 
B) (1R,2S)-1,2-dimethylcyclopentane 
C) (1S,2R)-1,2-dimethylcyclopentane 
D) (1S,2S)-1,2-dimethylcyclopentane

Question 17

Which of the following statements is true?

Accepted Answer

A) Achiral molecules usually contain a plane of symmetry. 
B) With one tetrahedral stereogenic center,a molecule may or may not be chiral. 
C) With two or more stereogenic centers,a molecule is always chiral. 
D) Chiral molecules usually contain a plane of symmetry. 
A) Achiral molecules usually contain a plane of symmetry. 
B) With one tetrahedral stereogenic center,a molecule may or may not be chiral. 
C) With two or more stereogenic centers,a molecule is always chiral. 
D) Chiral molecules usually contain a plane of symmetry.

Question 18

What is the relationship between the following two compounds?

Accepted Answer

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

Question 19

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?

Accepted Answer

A) 3)0 g 
B) 3)5 g 
C) 6)5 g 
D) 7)0 g 
A) 3)0 g 
B) 3)5 g 
C) 6)5 g 
D) 7)0 g

Question 20

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

Exam 5: Stereochemistry

Which of the following compounds has a plane of symmetry?

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

What is the relationship between the following compounds?

Give the IUPAC name for the following compound:

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

Which of the following compounds is a meso compound?

What is the relationship between the following compounds?

Which of the following statements is not true?

How many stereogenic centers are present in the following compound?

Which of the following compounds are chiral?

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

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

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

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

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

Give the IUPAC name for the following compound:

Which of the following statements is true?

What is the relationship between the following two compounds?

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?

Which of the following structures has the S 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 and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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