Question 1

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

Accepted Answer

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

Question 2

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 3

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 4

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 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 statements about constitutional isomers is 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 7

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 8

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 9

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 10

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 11

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

Accepted Answer

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

Question 12

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 13

Which of the following molecules has a plane of symmetry?

Accepted Answer

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

Question 14

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 15

Which of the following cyclic molecules is a meso compound?

Accepted Answer

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

Question 16

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.

Exam 5: Stereochemistry

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

What is the relationship between the following two compounds?

Which of the following statements is not true?

Which of the following compounds are meso?

What is the relationship between the following compounds?

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

Which of the following is the definition of chirality?

Give the IUPAC name for the following compound:

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

What is the relationship between the following compounds?

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

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

Which of the following molecules has a plane of symmetry?

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

Which of the following cyclic molecules is a meso compound?

Which of the following statements about stereoisomers is not true?

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

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