Question 1

Circle all structures shown below that are chiral.

Accepted Answer

The answer of Circle all structures shown below that are...

Question 2

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

Accepted Answer

The answer of Which of the following terms best describes...

Question 3

Draw the structure of any diastereomer of (2S, 3R)-2,3-dichloropentane. Take particular care to indicate three-dimensional stereochemical detail properly.

Accepted Answer

The answer of Draw the structure of any diastereomer of...

Question 4

Does the molecule shown below contain asymmetric carbon atoms? Is this molecule chiral?

Accepted Answer

Yes, the molecule contains 4 a

Question 5

If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of the mixture?

Accepted Answer

A)  100 
B)  75 
C)  50 
D)  25 
E)  3 
A)  100 
B)  75 
C)  50 
D)  25 
E)  3

Question 6

How many asymmetric carbon atoms are present in the molecule shown?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  4 
A)  0 
B)  1 
C)  2 
D)  3 
E)  4

Question 7

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

Accepted Answer

The answer of Which of the following terms best describes...

Question 8

Which of the following structures are achiral and meso?

Accepted Answer

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

Question 9

Translate the structure below to a Fischer projection.

Accepted Answer

The answer of Translate the structure below to a Fischer...

Question 10

If possible, draw the enantiomer of the molecule shown below.

Accepted Answer

This molecule is ach

Question 11

How many asymmetric carbons are present in the compound below?

Accepted Answer

The answer of How many asymmetric carbons are present in...

Question 12

Which of the following molecules, if isolated in its pure form, would demonstrate optical activity?

Accepted Answer

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

Question 13

Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take particular care to indicate stereochemistry properly.

Accepted Answer

The answer of Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take...

Question 14

Draw any diastereomer of the molecule shown below.

Accepted Answer

The answer of Draw any diastereomer of the molecule shown...

Question 15

Which of the following are acceptable Fischer projections for S-alanine, NH2CH(CH3)COOH?

Accepted Answer

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

Question 16

What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane?

Accepted Answer

A)  not isomers 
B)  constitutional isomers 
C)  enantiomers 
D)  diastereomers 
E)  conformers 
A)  not isomers 
B)  constitutional isomers 
C)  enantiomers 
D)  diastereomers 
E)  conformers

Question 17

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

Accepted Answer

The answer of Which of the following terms best describes...

Question 18

Consider the four substituents below. Order them in decreasing priority according to the Cahn-Ingold-Prelog priority system. (Highest priority is first, lowest is last.)
-D, -H, -CH3, -CH2CH3

Accepted Answer

1: -CH₂CH_3,2:

Question 19

Draw the Fischer projection of (S)-2-bromobutane.

Accepted Answer

The answer of Draw the Fischer projection of (S)-2-bromobutane....

Question 20

Can one predict whether a compound with a single asymmetric carbon is dextro- or levorotatory based on the R/S assignment at this asymmetric carbon? Explain briefly.

Accepted Answer

No. R/S assignment is purely a

Exam 5: Stereochemistry

Circle all structures shown below that are chiral.

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

Draw the structure of any diastereomer of (2S, 3R)-2,3-dichloropentane. Take particular care to indicate three-dimensional stereochemical detail properly.

Does the molecule shown below contain asymmetric carbon atoms? Is this molecule chiral?

If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of the mixture?

How many asymmetric carbon atoms are present in the molecule shown?

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

Which of the following structures are achiral and meso?

Translate the structure below to a Fischer projection.

If possible, draw the enantiomer of the molecule shown below.

How many asymmetric carbons are present in the compound below?

Which of the following molecules, if isolated in its pure form, would demonstrate optical activity?

Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take particular care to indicate stereochemistry properly.

Draw any diastereomer of the molecule shown below.

Which of the following are acceptable Fischer projections for S-alanine, NH2CH(CH3)COOH?

What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane?

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

Consider the four substituents below. Order them in decreasing priority according to the Cahn-Ingold-Prelog priority system. (Highest priority is first, lowest is last.) -D, -H, -CH3, -CH2CH3

Draw the Fischer projection of (S)-2-bromobutane.

Can one predict whether a compound with a single asymmetric carbon is dextro- or levorotatory based on the R/S assignment at this asymmetric carbon? Explain briefly.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Which of the following are acceptable Fischer projections for S-alanine, NH₂CH(CH₃)COOH?

Consider the four substituents below. Order them in decreasing priority according to the Cahn-Ingold-Prelog priority system. (Highest priority is first, lowest is last.) -D, -H, -CH₃, -CH₂CH₃