Question 1

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

Accepted Answer

A) 2 
B) 3 
C) 4 
D) 6 
A) 2 
B) 3 
C) 4 
D) 6 C

Question 2

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

Accepted Answer

A) 3 
B) 4 
C) 5 
D) 6 
A) 3 
B) 4 
C) 5 
D) 6 D

Question 3

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?

Accepted Answer

A) +50° 
B) -40° 
C) +40° 
D) -50° 
A) +50° 
B) -40° 
C) +40° 
D) -50° D

Question 4

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 5

Which of the following molecules are achiral?

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 6

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

Accepted Answer

A) 75 
B) 40 
C) 65 
D) 50 
A) 75 
B) 40 
C) 65 
D) 50

Question 7

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

Accepted Answer

A) Starch and cellulose are not stereoisomers. 
B) In cellulose, the O atom joins two rings using one equatorial and one axial bond. 
C) In starch, the O atom joins two rings using two equatorial bonds. 
D) In cellulose, the O atom joins two rings using two equatorial bonds. 
A) Starch and cellulose are not stereoisomers. 
B) In cellulose, the O atom joins two rings using one equatorial and one axial bond. 
C) In starch, the O atom joins two rings using two equatorial bonds. 
D) In cellulose, the O atom joins two rings using two equatorial bonds.

Question 8

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

Accepted Answer

A) 70 
B) 85 
C) 40 
D) 30 
A) 70 
B) 85 
C) 40 
D) 30

Question 9

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 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

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 12

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 13

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 14

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 15

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 16

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 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

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 19

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 20

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

Exam 5: Stereochemistry

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

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

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?

How many stereogenic centers are present in the following molecule?

Which of the following molecules are achiral?

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

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

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

Which of the following statements is true?

What is the relationship between the following compounds?

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

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

Which of the following statements is true?

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

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

What is the relationship between the following compounds?

What is the relationship between the following compounds?

How many stereogenic centers are present in the following compound?

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

Which of the following cyclic molecules is a meso compound?

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

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