Question 1

How many stereoisomers of 1,3-dibromocyclopentane exist?

Accepted Answer

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

Question 2

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 A

Question 3

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. A

Question 4

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 5

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 6

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 7

How many chiral stereoisomers can be drawn for dimethycyclopropane?

Accepted Answer

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

Question 8

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 9

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 10

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 11

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 12

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

Question 13

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 14

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 15

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 16

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

Question 17

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 18

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 19

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 20

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

Exam 5: Stereochemistry

How many stereoisomers of 1,3-dibromocyclopentane exist?

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

Which of the following statements is true?

What is the relationship between the following two compounds?

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

What is the relationship between the following compounds?

How many chiral stereoisomers can be drawn for dimethycyclopropane?

Which of the following compounds is a meso compound?

How many stereogenic centers are present in the following compound?

Give the IUPAC name for the following compound:

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

Which of the following structures has the R configuration?

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

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

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?

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

Give the IUPAC name for the following compound:

Which of the following compounds is identical to compound A?

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

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

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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