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

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

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 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

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 6

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.

Question 7

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

Accepted Answer

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

Question 8

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

Question 9

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 10

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 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

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 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 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 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

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.

Question 17

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 18

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 19

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°

Question 20

Which of the following statements about constitutional isomers if not true?

Accepted Answer

A)  They have different IUPAC names. 
B)  They always have the same functional groups. 
C)  They have different physical properties. 
D)  They have different chemical properties. 
A)  They have different IUPAC names. 
B)  They always have the same functional groups. 
C)  They have different physical properties. 
D)  They have different chemical properties.

Exam 5: Stereochemistry

How many stereoisomers of 1,3-dibromocyclopentane exist?

What is the relationship between the following compounds?

What is the relationship between the following two compounds?

What is the relationship between the following compounds?

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

Which of the following statements is true?

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

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

Which of the following compounds can have a meso stereoisomer?

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

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

Which of the following molecules are achiral?

What is the relationship between the following compounds?

Which of the following statements is true?

How many stereogenic centers are present in the following compound?

Which of the following molecules are chiral?

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.

Which of the following statements about constitutional isomers if not 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 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

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