Question 1

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 2

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 3

Use the following three structures to answer the questions below.  
-The relationship between I and II is: ________.

Accepted Answer

A)  same compound 
B)  enantiomers 
C)  diastereomers 
D)  constitutional isomers 
A)  same compound 
B)  enantiomers 
C)  diastereomers 
D)  constitutional isomers

Question 4

Label each asymmetric carbon in the compound below as R or S.

Accepted Answer

The answer of Label each asymmetric carbon in the compound...

Question 5

Provide a Fischer projection of (2S,3S,4S)-2,3,4-trichloroheptane.

Accepted Answer

The answer of Provide a Fischer projection of (2S,3S,4S)-2,3,4-trichloroheptane....

Question 6

If (S)-glyceraldehyde has a specific rotation of -8.7°, what is the specific rotation of (R)-glyceraldehyde?

Accepted Answer

A)  0.0° 
B)  -8.7° 
C)  +8.7° 
D)  cannot be determined from the information given 
A)  0.0° 
B)  -8.7° 
C)  +8.7° 
D)  cannot be determined from the information given

Question 7

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

Accepted Answer

The answer of If possible, draw the structure of the...

Question 8

Label each asymmetric carbon in the compound below as R or S.

Accepted Answer

The answer of Label each asymmetric carbon in the compound...

Question 9

Which of the following terms best describes the pair of compounds shown: $\underline{\text{  enantiomers, diastereomers }}$ , or $\underline{\text{ the same compound?  }}$

Accepted Answer

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

Question 10

Label each asymmetric carbon in the compound below as R or S.

Accepted Answer

The answer of Label each asymmetric carbon in the compound...

Question 11

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

Accepted Answer

The answer of Draw the structure of (2R,3S)-2,3-dichloropentane. Take particular...

Question 12

Draw the structure of the meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemical detail properly.

Accepted Answer

The answer of Draw the structure of the meso form...

Question 13

Which of the following $\underline{\text{ incorrectly  }}$ describes $\underline{\text{ cis }}$ -1,2-dimethylcyclopentane?

Accepted Answer

A)  It is a meso compound. 
B)  It is achiral. 
C)  It contains two asymmetric carbons. 
D)  Its diastereomer is $\underline{\text{trans  }}$ -1,2-dimethylcyclopentane. 
E)  It has an enantiomer. 
A)  It is a meso compound. 
B)  It is achiral. 
C)  It contains two asymmetric carbons. 
D)  Its diastereomer is $\underline{\text{trans  }}$ -1,2-dimethylcyclopentane. 
E)  It has an enantiomer.

Question 14

What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and (2S,3S,4R)-2,3,4-trichloroheptane?

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 15

Draw the Fischer projection of (2R,4R)-2,4-dibromopentane.

Accepted Answer

The answer of Draw the Fischer projection of (2R,4R)-2,4-dibromopentane....

Question 16

Which of the following statements correctly pertains to a pair of enantiomers?

Accepted Answer

A)  They rotate the plane of polarized light by exactly the same amount and in opposite directions. 
B)  They rotate the plane of polarized light by differing amounts and in opposite directions. 
C)  They rotate the plane of polarized light by differing amounts and in the same direction. 
D)  The have different melting points. 
E)  They have the same melting point, but they have different boiling points. 
A)  They rotate the plane of polarized light by exactly the same amount and in opposite directions. 
B)  They rotate the plane of polarized light by differing amounts and in opposite directions. 
C)  They rotate the plane of polarized light by differing amounts and in the same direction. 
D)  The have different melting points. 
E)  They have the same melting point, but they have different boiling points.

Question 17

Is the molecule shown below chiral or achiral?

Accepted Answer

The answer of Is the molecule shown below chiral or...

Question 18

What term describes the structural relationship between (E)- and (Z)-2-pentene?

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 19

A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?

Accepted Answer

The answer of A newly isolated natural product was shown...

Question 20

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

Exam 5: Stereochemistry

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

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

Use the following three structures to answer the questions below. -The relationship between I and II is: ________.

Label each asymmetric carbon in the compound below as R or S.

Provide a Fischer projection of (2S,3S,4S)-2,3,4-trichloroheptane.

If (S)-glyceraldehyde has a specific rotation of -8.7°, what is the specific rotation of (R)-glyceraldehyde?

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

Label each asymmetric carbon in the compound below as R or S.

Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers ‾\underline{\text{ enantiomers, diastereomers }} enantiomers, diastereomers ​ , or the same compound? ‾\underline{\text{ the same compound? }} the same compound? ​

Label each asymmetric carbon in the compound below as R or S.

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

Draw the structure of the meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemical detail properly.

Which of the following incorrectly ‾\underline{\text{ incorrectly }} incorrectly ​ describes cis ‾\underline{\text{ cis }} cis ​ -1,2-dimethylcyclopentane?

What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and (2S,3S,4R)-2,3,4-trichloroheptane?

Draw the Fischer projection of (2R,4R)-2,4-dibromopentane.

Which of the following statements correctly pertains to a pair of enantiomers?

Is the molecule shown below chiral or achiral?

What term describes the structural relationship between (E)- and (Z)-2-pentene?

A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?

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

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

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 $\underline{\text{ incorrectly }}$ describes $\underline{\text{ cis }}$ -1,2-dimethylcyclopentane?