Question 1

Which of the following statements is true?

Accepted Answer

A) Enantiomers are mirror images that are not superimposable. 
B) A molecule that is superimposable on its mirror image is chiral. 
C) A chiral molecule usually contains a plane of symmetry. 
D) An achiral molecule does not contain a plane of symmetry. 
A) Enantiomers are mirror images that are not superimposable. 
B) A molecule that is superimposable on its mirror image is chiral. 
C) A chiral molecule usually contains a plane of symmetry. 
D) An achiral molecule does not contain a plane of symmetry.

Question 2

Give the IUPAC name for the following compound:

Accepted Answer

A) R-3-methylhexane 
B) S-3-methylhexane 
C) R-4-methylhexane 
D) S-4-methylhexane 
A) R-3-methylhexane 
B) S-3-methylhexane 
C) R-4-methylhexane 
D) S-4-methylhexane

Question 3

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 4

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 5

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

Accepted Answer

A) A pair of stereoisomers that have a plane of symmetry. 
B) A pair of stereoisomers that are not 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 superimposable mirror images of each other. 
A) A pair of stereoisomers that have a plane of symmetry. 
B) A pair of stereoisomers that are not 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 superimposable mirror images of each other.

Question 6

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 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

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 9

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 10

How many stereogenic centers are present in the following molecule?

Accepted Answer

A) 1 
B) 2 
C) 4 
D) 5 
A) 1 
B) 2 
C) 4 
D) 5

Question 11

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

Accepted Answer

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

Question 12

Which of the following statements about stereoisomers is not true?

Accepted Answer

A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans. 
B) Stereoisomers differ in configuration. 
C) Stereoisomers always have the same functional groups. 
D) Stereoisomers differ only in their structural formula. 
A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans. 
B) Stereoisomers differ in configuration. 
C) Stereoisomers always have the same functional groups. 
D) Stereoisomers differ only in their structural formula.

Question 13

How many stereogenic centers are present in menthol?

Accepted Answer

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

Question 14

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 15

Which of the following compounds is identical to compound A?

Accepted Answer

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

Question 16

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 statements is true?

Give the IUPAC name for the following compound:

How many stereogenic centers are present in the following compound?

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?

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

Which of the following compounds are meso?

What is the relationship between the following compounds?

What is the relationship between the following two compounds?

Which of the following molecules are chiral?

How many stereogenic centers are present in the following molecule?

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

Which of the following statements about stereoisomers is not true?

How many stereogenic centers are present in menthol?

What is the relationship between the following compounds?

Which of the following compounds is identical to compound A?

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 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

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