Question 1

Which of the following is the definition of a meso compound?

Accepted Answer

A)  A molecule with stereocenter centers which is chiral 
B)  A molecule with stereocenter centers which is not chiral 
C)  A diastereomer with no stereocenter centers 
D)  A chiral compound with more than one stereocenter center 
A)  A molecule with stereocenter centers which is chiral 
B)  A molecule with stereocenter centers which is not chiral 
C)  A diastereomer with no stereocenter centers 
D)  A chiral compound with more than one stereocenter center

Question 2

What is the relationship between the following pair of structures?

Accepted Answer

A)  They are enantiomers 
B)  They are diastereomers 
C)  The are constitutional isomers 
D)  They are identical 
A)  They are enantiomers 
B)  They are diastereomers 
C)  The are constitutional isomers 
D)  They are identical

Question 3

What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)

Accepted Answer

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

Question 4

Which of the following compounds is a meso compound?

Accepted Answer

A)  (2R,3R)-dibromobutane 
B)  (2R,3S)-dibromobutane 
C)  (2R,3S)-3-bromo-2-butanol 
D)  (2R,3R)-3-bromo-2-butanol 
A)  (2R,3R)-dibromobutane 
B)  (2R,3S)-dibromobutane 
C)  (2R,3S)-3-bromo-2-butanol 
D)  (2R,3R)-3-bromo-2-butanol

Question 5

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?

Accepted Answer

A)  -NH2 
B)  -NHCH3 
C)  -CH2NH2 
D)  -CH2NHCH3 
A)  -NH2 
B)  -NHCH3 
C)  -CH2NH2 
D)  -CH2NHCH3

Question 6

Which of the following have the S configuration?

Accepted Answer

A)  only 1 
B)  only 2 
C)  only 1 and 2 
D)  1, 2 and 3 
A)  only 1 
B)  only 2 
C)  only 1 and 2 
D)  1, 2 and 3

Question 7

What is the relationship between the following pair of structures?

Accepted Answer

A)  They are enantiomers 
B)  They are diastereomers 
C)  The are constitutional isomers 
D)  They are identical 
A)  They are enantiomers 
B)  They are diastereomers 
C)  The are constitutional isomers 
D)  They are identical

Question 8

Which of the following structures has a center of symmetry (i.e., center of inversion)?

Accepted Answer

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

Question 9

Which of the following compounds is/are chiral?

Accepted Answer

A)  only 1 
B)  only 1 and 2 
C)  only 2 and 3 
D)  1, 2 and 3 
A)  only 1 
B)  only 1 and 2 
C)  only 2 and 3 
D)  1, 2 and 3

Question 10

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

Accepted Answer

A)  A pair of structures that are superposable mirror images of one another 
B)  A pair of stereoisomers that are non-superposable mirror images of one another 
C)  A pair of stereoisomers that are not mirror images of one another 
D)  A pair of stereoisomers that have equal specific rotations 
A)  A pair of structures that are superposable mirror images of one another 
B)  A pair of stereoisomers that are non-superposable mirror images of one another 
C)  A pair of stereoisomers that are not mirror images of one another 
D)  A pair of stereoisomers that have equal specific rotations

Question 11

The specific rotation of the S-enantiomer of a compound is -120$\degree$. What is the enantiomeric excess of a sample of the compound that has a measured specific rotation of -30$\degree$.

Accepted Answer

ee = 25% o

Question 12

Which of the following structures represent the same stereoisomer?

Accepted Answer

A)  only 1 and 2 
B)  only 1 and 3 
C)  only 2 and 3 
D)  1, 2 and 3 
A)  only 1 and 2 
B)  only 1 and 3 
C)  only 2 and 3 
D)  1, 2 and 3

Question 13

Which of the following compounds is/are chiral?

Accepted Answer

A)  only 1 
B)  only 1 and 2 
C)  only 2 and 3 
D)  1, 2 and 3 
A)  only 1 
B)  only 1 and 2 
C)  only 2 and 3 
D)  1, 2 and 3

Question 14

A solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4.8$\degree$. What is the rotation observed on this solution in a 2 dm polarimeter?

Accepted Answer

A)  +2.4$\degree$ 
B)  +4.8$\degree$ 
C)  +9.6$\degree$ 
D)  +19.2$\degree$ 
A)  +2.4$\degree$ 
B)  +4.8$\degree$ 
C)  +9.6$\degree$ 
D)  +19.2$\degree$

Question 15

How many stereogenic centers are there in the following molecule (the naturally occurring stereoisomer is camphor, a pungent moth repellent)?

Accepted Answer

A)  Two 
B)  Three 
C)  Four 
D)  Five 
A)  Two 
B)  Three 
C)  Four 
D)  Five

Which of the following is the definition of a meso compound?

What is the relationship between the following pair of structures?

What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)

Which of the following compounds is a meso compound?

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?

Which of the following have the S configuration?

What is the relationship between the following pair of structures?

Which of the following structures has a center of symmetry (i.e., center of inversion)?

Which of the following compounds is/are chiral?

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

The specific rotation of the S-enantiomer of a compound is -120 $\degree$ . What is the enantiomeric excess of a sample of the compound that has a measured specific rotation of -30 $\degree$ .

Which of the following structures represent the same stereoisomer?

Which of the following compounds is/are chiral?

A solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4.8 $\degree$ . What is the rotation observed on this solution in a 2 dm polarimeter?

How many stereogenic centers are there in the following molecule (the naturally occurring stereoisomer is camphor, a pungent moth repellent)?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Filters

Exam 3: Stereoisomerism and Chirality

Which of the following is the definition of a meso compound?

What is the relationship between the following pair of structures?

What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)

Which of the following compounds is a meso compound?

Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?

Which of the following have the S configuration?

What is the relationship between the following pair of structures?

Which of the following structures has a center of symmetry (i.e., center of inversion)?

Which of the following compounds is/are chiral?

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

The specific rotation of the S-enantiomer of a compound is -120 °\degree° . What is the enantiomeric excess of a sample of the compound that has a measured specific rotation of -30 °\degree° .

Which of the following structures represent the same stereoisomer?

Which of the following compounds is/are chiral?

A solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4.8 °\degree° . What is the rotation observed on this solution in a 2 dm polarimeter?

How many stereogenic centers are there in the following molecule (the naturally occurring stereoisomer is camphor, a pungent moth repellent)?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Filters

The specific rotation of the S-enantiomer of a compound is -120 $\degree$ . What is the enantiomeric excess of a sample of the compound that has a measured specific rotation of -30 $\degree$ .

A solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4.8 $\degree$ . What is the rotation observed on this solution in a 2 dm polarimeter?