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

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 3

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 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

How many stereogenic centers are present in menthol?

Accepted Answer

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

Question 6

Which of the following molecules are chiral?

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 7

How many stereogenic centers are present in ephedrine,a bronchodilator and decongestant?

Accepted Answer

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

Question 8

How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH)CH3?

Accepted Answer

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

Question 9

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 10

Which of the following compounds are chiral?

Accepted Answer

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

Question 11

Which of the following statements about meso compounds is not true?

Accepted Answer

A) A meso compound generally has a plane of symmetry. 
B) A meso compound and its mirror image are identical. 
C) A meso compound is achiral. 
D) A meso compound is chiral. 
A) A meso compound generally has a plane of symmetry. 
B) A meso compound and its mirror image are identical. 
C) A meso compound is achiral. 
D) A meso compound is chiral.

Question 12

A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°.What is the specific rotation of the S enantiomer?

Accepted Answer

A) +50° 
B) -40° 
C) +40° 
D) -50° 
A) +50° 
B) -40° 
C) +40° 
D) -50°

Question 13

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 14

Give the IUPAC name for the following compound:

Accepted Answer

A) (1R,2R)-1,2-dimethylcyclopentane 
B) (1R,2S)-1,2-dimethylcyclopentane 
C) (1S,2R)-1,2-dimethylcyclopentane 
D) (1S,2S)-1,2-dimethylcyclopentane 
A) (1R,2R)-1,2-dimethylcyclopentane 
B) (1R,2S)-1,2-dimethylcyclopentane 
C) (1S,2R)-1,2-dimethylcyclopentane 
D) (1S,2S)-1,2-dimethylcyclopentane

Question 15

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 16

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 17

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 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

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 20

A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°.What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?

Accepted Answer

A) +5.6° 
B) +11.2° 
C) +2.8° 
D) +1.4° 
A) +5.6° 
B) +11.2° 
C) +2.8° 
D) +1.4°

Exam 5: Stereochemistry

What is the relationship between the following compounds?

What is the relationship between the following compounds?

How many stereogenic centers are present in the following compound?

What is the relationship between the following compounds?

How many stereogenic centers are present in menthol?

Which of the following molecules are chiral?

How many stereogenic centers are present in ephedrine,a bronchodilator and decongestant?

How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH)CH3?

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 are chiral?

Which of the following statements about meso compounds is not true?

A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°.What is the specific rotation of the S enantiomer?

Which of the following structures has the R configuration?

Give the IUPAC name for the following compound:

A reaction mixture is three parts of one enantiomer and one part of the other.What is the percent ee of this mixture?

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

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

How many stereogenic centers are present in the following molecule?

What is the relationship between the following compounds?

A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°.What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?

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 are possible for a molecule with formula CH₃CHBrCH(OH)CH₃?

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?