Question 1

Which of the following terms best describes the stereochemical relationship of the two compounds shown below in Fischer notation?

Accepted Answer

A)  enantiomers 
B)  diastereomers 
C)  constitutional isomers 
D)  cis/trans - isomers 
E)  meso - same structure 
A)  enantiomers 
B)  diastereomers 
C)  constitutional isomers 
D)  cis/trans - isomers 
E)  meso - same structure

Question 2

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

Accepted Answer

This molecule is ach

Question 3

Which of the following terms correctly describe(s) the structural relationship between cis-1,3-dimethylcyclopentane and trans-1,3-dimethylcyclopentane?

Accepted Answer

A)  enantiomers 
B)  diastereomers 
C)  geometric isomers 
D)  both A and C 
E)  both B and C 
A)  enantiomers 
B)  diastereomers 
C)  geometric isomers 
D)  both A and C 
E)  both B and C

Question 4

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 5

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 6

What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and (2S,3S,5R)-2,3,5-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 7

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

Accepted Answer

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

Question 8

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 9

For the structure shown below, draw the stereoisomer having a configuration of (1R,3S,4S) in a perspective structure.

Accepted Answer

The answer of For the structure shown below, draw the...

Question 10

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 11

How many asymmetric carbons are present in the compound below?
3-ethyl-2,2,4-trimethylpentane

Accepted Answer

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

Question 12

How many diastereomers are there of the molecule shown below?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  6 
A)  0 
B)  1 
C)  2 
D)  3 
E)  6

Question 13

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 14

Phantasmidine, shown below, is found in poisonous frog skin and has analgesic properties (J. Nat. Prod. 2010, 331). Assign each chiral center as having either R or S configuration.

Accepted Answer

The answer of Phantasmidine, shown below, is found in poisonous...

Question 15

Which of the following statements is (are) true for the compound (R)-2-butanol?

Accepted Answer

A)  This compound is chiral. 
B)  This compound is optically active. 
C)  This compound has an enantiomer. 
D)  all of the above 
E)  none of the above 
A)  This compound is chiral. 
B)  This compound is optically active. 
C)  This compound has an enantiomer. 
D)  all of the above 
E)  none of the above

Question 16

Why is the following structure not a meso compound?

Accepted Answer

The functional group at the to

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

Draw the structure of the enantiomer 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 the enantiomer of...

Question 19

Draw the structure of (2R,3R)-2,3-dibromo-3-chloropentane.

Accepted Answer

The answer of Draw the structure of (2R,3R)-2,3-dibromo-3-chloropentane....

Question 20

Glucose has a specific rotation of +52.8°. Predict the concentration of a glucose aqueous solution contained in a 10 cm long polarimetry tube if a rotation of +15.8° was observed.

Accepted Answer

A)  0.299 g/mL 
B)  0299 g/mL 
C)  3.34 g/mL 
D)  334 g/mL 
A)  0.299 g/mL 
B)  0299 g/mL 
C)  3.34 g/mL 
D)  334 g/mL

Exam 5: Stereochemistry

Which of the following terms best describes the stereochemical relationship of the two compounds shown below in Fischer notation?

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

Which of the following terms correctly describe(s) the structural relationship between cis-1,3-dimethylcyclopentane and trans-1,3-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 structure of the meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemical detail properly.

What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and (2S,3S,5R)-2,3,5-trichloroheptane?

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

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?

For the structure shown below, draw the stereoisomer having a configuration of (1R,3S,4S) in a perspective structure.

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

How many asymmetric carbons are present in the compound below? 3-ethyl-2,2,4-trimethylpentane

How many diastereomers are there of the molecule shown below?

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

Phantasmidine, shown below, is found in poisonous frog skin and has analgesic properties (J. Nat. Prod. 2010, 331). Assign each chiral center as having either R or S configuration.

Which of the following statements is (are) true for the compound (R)-2-butanol?

Why is the following structure not a meso compound?

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

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

Draw the structure of (2R,3R)-2,3-dibromo-3-chloropentane.

Glucose has a specific rotation of +52.8°. Predict the concentration of a glucose aqueous solution contained in a 10 cm long polarimetry tube if a rotation of +15.8° was observed.

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

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Condensations and Alpha Substitutions of Carboxyl Compounds

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