Question 1

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 2

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 3

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 4

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 5

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 6

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 7

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 8

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 9

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 10

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

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 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 12

How many stereogenic centers are present in the following compound?

Accepted Answer

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

Question 13

Which of the following molecules are chiral? I.2-Chlorobutane
II)3-Bromopentane
III)1-Bromo-2-methylpropene
IV)2-Bromo-3-methylbutane

Accepted Answer

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

Question 14

Which of the following compounds has a plane of symmetry?

Accepted Answer

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

Question 15

Which of the following is the definition for a pair of diastereomers?

Accepted Answer

A) A pair of stereoisomers with stereogenic centers but is not chiral. 
B) A pair of stereoisomers that are superimposable 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 not mirror images of each other. 
A) A pair of stereoisomers with stereogenic centers but is not chiral. 
B) A pair of stereoisomers that are superimposable 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 not mirror images of each other.

Question 16

How many stereoisomers can be drawn for a molecule with formula CH3CH(OH)CH(OH)CH3?

Accepted Answer

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

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

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 19

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 20

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.

Exam 5: Stereochemistry

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

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?

How many stereogenic centers are present in the following compound?

Give the IUPAC name for the following compound:

Which of the following structures has the S configuration?

What is the relationship between the following two compounds?

What is the relationship between the following two compounds?

Give the IUPAC name for the following compound:

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

Which of the following statements is true?

How many stereogenic centers are present in the following compound?

Which of the following molecules are chiral? I.2-Chlorobutane II)3-Bromopentane III)1-Bromo-2-methylpropene IV)2-Bromo-3-methylbutane

Which of the following compounds has a plane of symmetry?

Which of the following is the definition for a pair of diastereomers?

How many stereoisomers can be drawn for a molecule with formula CH3CH(OH)CH(OH)CH3?

What is the relationship between the following compounds?

Which of the following compounds can have a meso stereoisomer?

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

Which of the following statements is 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

Filters

How many stereoisomers can be drawn for a molecule with formula CH₃CH(OH)CH(OH)CH₃?