Question 1

Which structure represents (S)-2-bromobutane?

Accepted Answer

A) I 
B) II 
C) III 
D) More than one of these choices. 
E) None of these choices. 
A) I 
B) II 
C) III 
D) More than one of these choices. 
E) None of these choices.

Question 2

What is the correct stereochemistry for the indicated stereocenters in (+)-camphor?

Accepted Answer

A) 1R,4R 
B) 1R,4S 
C) 1S,4S 
D) 1S,4R 
E) None,molecule is not chiral. 
A) 1R,4R 
B) 1R,4S 
C) 1S,4S 
D) 1S,4R 
E) None,molecule is not chiral.

Question 3

The molecules below are:

Accepted Answer

A) enantiomers. 
B) diastereomers. 
C) constitutional isomers. 
D) two different conformations of the same molecule. 
E) not isomeric. 
A) enantiomers. 
B) diastereomers. 
C) constitutional isomers. 
D) two different conformations of the same molecule. 
E) not isomeric.

Question 4

Draw a dash-wedge structure for (1S,2S,5R)-5-methyl-2-propylcyclohexanol

Accepted Answer

The answer of Draw a dash-wedge structure for (1S,2S,5R)-5-methyl-2-propylcyclohexanol...

Question 5

Which compound would show optical activity?

Accepted Answer

A) cis-1,4-Dimethylcyclohexane 
B) trans-1,4-Dimethylcyclohexane 
C) cis-1,4-Dimethylcycloheptane 
D) trans-1,4-Dimethylcycloheptane 
E) More than one of these choices. 
A) cis-1,4-Dimethylcyclohexane 
B) trans-1,4-Dimethylcyclohexane 
C) cis-1,4-Dimethylcycloheptane 
D) trans-1,4-Dimethylcycloheptane 
E) More than one of these choices.

Question 6

Which molecule is a meso compound?

Accepted Answer

A) I 
B) II 
C) III 
D) More than one of these choices. 
E) None of these choices. 
A) I 
B) II 
C) III 
D) More than one of these choices. 
E) None of these choices.

Question 7

Draw a dash-wedge structure for (R)-3-methyl-5-hexen-3-ol

Accepted Answer

The answer of Draw a dash-wedge structure for (R)-3-methyl-5-hexen-3-ol...

Question 8

Draw a dash-wedge structure for (3S,5R)-5-chloro-3-isopropylcyclohex-1-ene

Accepted Answer

The answer of Draw a dash-wedge structure for (3S,5R)-5-chloro-3-isopropylcyclohex-1-ene...

Question 9

Which compound does NOT possess a plane of symmetry?

Accepted Answer

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

Question 10

A sample consisting of the pure R enantiomer of a compound will always rotate plane-polarized light in a clockwise direction.

Accepted Answer

A) True 
 B)False

Question 11

I and II are:

Accepted Answer

A) constitutional isomers. 
B) enantiomers. 
C) identical. 
D) diastereomers. 
E) not isomeric. 
A) constitutional isomers. 
B) enantiomers. 
C) identical. 
D) diastereomers. 
E) not isomeric.

Question 12

The molecules below are:

Accepted Answer

A) constitutional isomers. 
B) enantiomers. 
C) diastereomers. 
D) identical. 
E) stereoisomers. 
A) constitutional isomers. 
B) enantiomers. 
C) diastereomers. 
D) identical. 
E) stereoisomers.

Question 13

What is the percent composition of a mixture of (S)-(+)-2-butanol,[$\alpha$]       = +13.52,and (R)-(-)-2-butanol,[$\alpha$]    
 = -13.52,with a specific rotation [$\alpha$]    
  = +6.76?

Accepted Answer

A) 75% (R),25% (S) 
B) 25% (R),75% (S) 
C) 50% (R),50% (S) 
D) 67% (R),33% (S) 
E) 33% (R),67% (S) 
A) 75% (R),25% (S) 
B) 25% (R),75% (S) 
C) 50% (R),50% (S) 
D) 67% (R),33% (S) 
E) 33% (R),67% (S)

Question 14

I and II are:

Accepted Answer

A) constitutional isomers. 
B) enantiomers. 
C) identical. 
D) diastereomers. 
E) not isomeric. 
A) constitutional isomers. 
B) enantiomers. 
C) identical. 
D) diastereomers. 
E) not isomeric.

Question 15

I and II are:

Accepted Answer

A) constitutional isomers. 
B) enantiomers. 
C) identical. 
D) diastereomers. 
E) not isomeric. 
A) constitutional isomers. 
B) enantiomers. 
C) identical. 
D) diastereomers. 
E) not isomeric.

Question 16

How many stereogenic centers are in the following compound:

Accepted Answer

A) 1 
B) 3 
C) 4 
D) 5 
E) none of these choices 
A) 1 
B) 3 
C) 4 
D) 5 
E) none of these choices

Question 17

If a solution of a compound (30.0 g/100 mL of solution)has a measured rotation of +15º in a 2.0 dm tube,the specific rotation is:

Accepted Answer

A) +50 
B) +25 
C) +15 
D) +7.5 
E) +4.0 
A) +50 
B) +25 
C) +15 
D) +7.5 
E) +4.0

Question 18

A diastereomeric mixture can be very difficult to purify as both isomers have the same physical properties.

Accepted Answer

A) True 
 B)False

Question 19

A chiral molecule was found to have a specific rotation of +19.5,thus we can conclude that the enantiomer of this compound will have a rotation that is equal and opposite in value.

Accepted Answer

A) True 
 B)False

Question 20

Draw a dash-wedge structure for (2R,3S)-2-bromo-3-chlorohexane

Accepted Answer

The answer of Draw a dash-wedge structure for (2R,3S)-2-bromo-3-chlorohexane...

Exam 5: Stereochemistry

Which structure represents (S)-2-bromobutane?

What is the correct stereochemistry for the indicated stereocenters in (+)-camphor?

The molecules below are:

Draw a dash-wedge structure for (1S,2S,5R)-5-methyl-2-propylcyclohexanol

Which compound would show optical activity?

Which molecule is a meso compound?

Draw a dash-wedge structure for (R)-3-methyl-5-hexen-3-ol

Draw a dash-wedge structure for (3S,5R)-5-chloro-3-isopropylcyclohex-1-ene

Which compound does NOT possess a plane of symmetry?

A sample consisting of the pure R enantiomer of a compound will always rotate plane-polarized light in a clockwise direction.

I and II are:

The molecules below are:

What is the percent composition of a mixture of (S)-(+)-2-butanol,[ α\alphaα ] = +13.52,and (R)-(-)-2-butanol,[ α\alphaα ] = -13.52,with a specific rotation [ α\alphaα ] = +6.76?

I and II are:

I and II are:

How many stereogenic centers are in the following compound:

If a solution of a compound (30.0 g/100 mL of solution)has a measured rotation of +15º in a 2.0 dm tube,the specific rotation is:

A diastereomeric mixture can be very difficult to purify as both isomers have the same physical properties.

A chiral molecule was found to have a specific rotation of +19.5,thus we can conclude that the enantiomer of this compound will have a rotation that is equal and opposite in value.

Draw a dash-wedge structure for (2R,3S)-2-bromo-3-chlorohexane

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

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