Question 1

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 2

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 3

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 4

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 5

Which of the following structures has the S 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 6

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system. $$\begin{array} { c c c c } 
- \mathrm { CH } = \mathrm { CH } _ { 2 } & - \mathrm { CH } _ { 3 } & - \mathrm { CHO } & - \mathrm { OH } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

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 7

How many stereogenic centers are present in fructose, a simple sugar?

Accepted Answer

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

Question 8

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 9

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 10

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system. $$\begin{array} { c c c c } 
- \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } & - \mathrm { CH } _ { 3 } & - \mathrm { H } & - \mathrm { CH } \left( \mathrm { CH } _ { 3 } \right) _ { 2 } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 11

Which of the following molecules has a plane of symmetry? $$\begin{array}{l}
\begin{array} { l l l l } 
\text {$\mathrm { CHBrClF }$}&
\text {$\mathrm { CH } _ { 2 } \mathrm { BrCl }$}&
\text {$\mathrm { CH } _ { 3 } \mathrm { CHClBr }$}&
\text {$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHBrF }$}\
I&II&III&IV
\end{array}
\end{array}$$

Accepted Answer

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

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

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 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

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 16

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 17

How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
A)  0 
B)  1 
C)  2 
D)  3

Question 18

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 19

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 20

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system. $$\begin{array} { c c c c } 
- \mathrm { COOH } & - \mathrm { H } & - \mathrm { NH } _ { 2 } & - \mathrm { OH } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

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

Exam 5: Stereochemistry

What is the relationship between the following compounds?

Which of the following compounds are meso?

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

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 structures has the S configuration?

Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system. -= - - - I II III IV

How many stereogenic centers are present in fructose, a simple sugar?

How many stereogenic centers are present in the following compound?

Which of the following structures has the R configuration?

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

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

What is the relationship between the following two compounds?

What is the relationship between the following compounds?

What is the relationship between the following compounds?

What is the relationship between the following two compounds?

How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

How many stereogenic centers are present in the following molecule?

Which of the following structures has the R configuration?

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

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 Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Lipids

Synthetic Polymers

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?