Question 1

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 2

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

Accepted Answer

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

Question 3

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 4

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 5

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 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 is true?

Accepted Answer

A) The presence of a plane of symmetry makes a molecule chiral. 
B) An achiral molecule must have one or more stereogenic centers. 
C) All molecules that have stereogenic centers are chiral. 
D) Stereoisomers that are not superimposable on their mirror image are enantiomers. 
A) The presence of a plane of symmetry makes a molecule chiral. 
B) An achiral molecule must have one or more stereogenic centers. 
C) All molecules that have stereogenic centers are chiral. 
D) Stereoisomers that are not superimposable on their mirror image are enantiomers.

Question 8

Give the IUPAC name for the following compound:

Accepted Answer

A) R-2,3-dimethylhexane 
B) S-2,3-dimethylhexane 
C) R-4,5-dimethylhexane 
D) S-4,5-dimethylhexane 
A) R-2,3-dimethylhexane 
B) S-2,3-dimethylhexane 
C) R-4,5-dimethylhexane 
D) S-4,5-dimethylhexane

Question 9

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

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

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 12

Which of the following molecules are chiral? I.cis-1,3-Dibromocyclohexane
II)1-Bromo-1-methylcyclohexane
III)trans-1-Bromo-3-methylcyclohexane
IV)cis-1-Bromo-3-methylcyclohexane

Accepted Answer

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

Question 13

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 14

What is the main carbohydrate in the seeds and roots of plants?

Accepted Answer

A) Starch 
B) Glucose 
C) Cellulose 
D) Glycogen 
A) Starch 
B) Glucose 
C) Cellulose 
D) Glycogen

Question 15

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 16

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 17

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 18

A natural product was isolated in the laboratory,and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O.What is the specific rotation of this compound?

Accepted Answer

A) -10° 
B) +100° 
C) +10° 
D) -100° 
A) -10° 
B) +100° 
C) +10° 
D) -100°

Question 19

Which of the following compounds can have a meso stereoisomer?

Accepted Answer

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

Question 20

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

Exam 5: Stereochemistry

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

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

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

What is the relationship between the following compounds?

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

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 is true?

Give the IUPAC name for the following compound:

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

What is the relationship between the following compounds?

What is the relationship between the following compounds?

Which of the following molecules are chiral? I.cis-1,3-Dibromocyclohexane II)1-Bromo-1-methylcyclohexane III)trans-1-Bromo-3-methylcyclohexane IV)cis-1-Bromo-3-methylcyclohexane

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

What is the main carbohydrate in the seeds and roots of plants?

What is the relationship between the following two compounds?

Which of the following molecules are achiral?

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

A natural product was isolated in the laboratory,and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O.What is the specific rotation of this compound?

Which of the following compounds can have a meso stereoisomer?

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

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

A natural product was isolated in the laboratory,and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H₂O.What is the specific rotation of this compound?