Question 1

Which of the statements below correctly describes the chair conformations of

Accepted Answer

A)  The two chair conformations are of equal energy. 
B)  The higher energy chair conformation contains one axial methyl group and one equatorial methyl group. 
C)  The lower energy chair conformation contains one axial methyl group and one equatorial methyl group. 
D)  The higher energy chair conformation contains two axial methyl groups. 
E)  The lower energy chair conformation contains two axial methyl groups. 
A)  The two chair conformations are of equal energy. 
B)  The higher energy chair conformation contains one axial methyl group and one equatorial methyl group. 
C)  The lower energy chair conformation contains one axial methyl group and one equatorial methyl group. 
D)  The higher energy chair conformation contains two axial methyl groups. 
E)  The lower energy chair conformation contains two axial methyl groups. D

Question 2

Provide an acceptable name for the following compound.

Accepted Answer

isobutylcyclopentane or (2-methylpropyl)cyclopentane

Question 3

Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane.

Accepted Answer

The answer of Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane....

Question 4

Use a sawhorse structure to depict the eclipsed conformer of ethane.

Accepted Answer

The answer of Use a sawhorse structure to depict the...

Question 5

The structure below is a potent analgesic agent (pain reliever) (J. Med. Chem., 2009, 5685). How many secondary carbons are in this structure?

Accepted Answer

A)  2 
B)  4 
C)  6 
D)  12 
A)  2 
B)  4 
C)  6 
D)  12

Question 6

Which of the following best describes the molecules of a sample of ethane gas at room temperature?

Accepted Answer

A)  Almost all of the molecules are frozen or locked in the eclipsed conformation. 
B)  Almost all of the molecules are frozen or locked in the staggered conformation. 
C)  The molecules are rapidly interconverting between the eclipsed and staggered conformations, but at any one time slightly more of them are present in the eclipsed conformation. 
D)  The molecules are rapidly interconverting between the eclipsed and staggered conformations, but at any one time slightly more of them are present in the staggered conformation. 
A)  Almost all of the molecules are frozen or locked in the eclipsed conformation. 
B)  Almost all of the molecules are frozen or locked in the staggered conformation. 
C)  The molecules are rapidly interconverting between the eclipsed and staggered conformations, but at any one time slightly more of them are present in the eclipsed conformation. 
D)  The molecules are rapidly interconverting between the eclipsed and staggered conformations, but at any one time slightly more of them are present in the staggered conformation.

Question 7

Provide an acceptable name for the alkane shown below.

Accepted Answer

5-sec-butyl-2,2-dime

Question 8

Draw a Newman Projection along the C3-C4 for the molecule shown below. (C3 should be in front.)

Accepted Answer

The answer of Draw a Newman Projection along the C3-C4...

Question 9

Draw the most stable conformation of trans-1,2-dimethylcyclohexane.

Accepted Answer

The answer of Draw the most stable conformation of trans-1,2-dimethylcyclohexane....

Question 10

Draw a Newman projection of the most stable conformation of 2-methylpropane.

Accepted Answer

The answer of Draw a Newman projection of the most...

Question 11

Identify the correct IUPAC name for the following structure.

Accepted Answer

A)  6-bromo-1-cyclopentyl-3,6-dimethylhexane 
B)  1-bromo-5-cyclopentyl-1,4-dimethylpentane 
C)  2-bromo-6-cyclopentyl-5-methylhexane 
D)  5-bromo-1-cyclopentyl-2-methylhexane 
E)  none of the above 
A)  6-bromo-1-cyclopentyl-3,6-dimethylhexane 
B)  1-bromo-5-cyclopentyl-1,4-dimethylpentane 
C)  2-bromo-6-cyclopentyl-5-methylhexane 
D)  5-bromo-1-cyclopentyl-2-methylhexane 
E)  none of the above

Question 12

Provide the name of the compound below.

Accepted Answer

3-fluoro-2

Question 13

Provide an acceptable name for the compound below.

Accepted Answer

bicyclo[2.

Question 14

Predict the molecular formula of 4-ethyl-5,5-dimethyldodecane.

Accepted Answer

The answer of Predict the molecular formula of 4-ethyl-5,5-dimethyldodecane....

Question 15

A bicyclic alkane contains 12 carbon atoms. How many hydrogen atoms does it contain?

Accepted Answer

A)  20 
B)  22 
C)  24 
D)  26 
E)  28 
A)  20 
B)  22 
C)  24 
D)  26 
E)  28

Question 16

Provide a Newman Projection of the gauche conformer of butane.

Accepted Answer

The answer of Provide a Newman Projection of the gauche...

Question 17

Draw the most stable conformation of trans-decalin.

Accepted Answer

The answer of Draw the most stable conformation of trans-decalin....

Question 18

Triacontane is an unbranched alkane that contains 30 carbon atoms in each molecule. How many hydrogen atoms are present in each molecule of triacontane?

Accepted Answer

A)  30 
B)  32 
C)  58 
D)  60 
E)  62 
A)  30 
B)  32 
C)  58 
D)  60 
E)  62

Question 19

Draw an acceptable structure for 4-tert-butyloctane.

Accepted Answer

The answer of Draw an acceptable structure for 4-tert-butyloctane....

Question 20

By using the appropriate molecular formulas, write a balanced equation which describes the complete combustion of nonane.

Accepted Answer

CH₃(CH₂)₇CH₃ +

Exam 3: Structure and Stereochemistry of Alkanes

Which of the statements below correctly describes the chair conformations of

Provide an acceptable name for the following compound.

Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane.

Use a sawhorse structure to depict the eclipsed conformer of ethane.

The structure below is a potent analgesic agent (pain reliever) (J. Med. Chem., 2009, 5685). How many secondary carbons are in this structure?

Which of the following best describes the molecules of a sample of ethane gas at room temperature?

Provide an acceptable name for the alkane shown below.

Draw a Newman Projection along the C3-C4 for the molecule shown below. (C3 should be in front.)

Draw the most stable conformation of trans-1,2-dimethylcyclohexane.

Draw a Newman projection of the most stable conformation of 2-methylpropane.

Identify the correct IUPAC name for the following structure.

Provide the name of the compound below.

Provide an acceptable name for the compound below.

Predict the molecular formula of 4-ethyl-5,5-dimethyldodecane.

A bicyclic alkane contains 12 carbon atoms. How many hydrogen atoms does it contain?

Provide a Newman Projection of the gauche conformer of butane.

Draw the most stable conformation of trans-decalin.

Triacontane is an unbranched alkane that contains 30 carbon atoms in each molecule. How many hydrogen atoms are present in each molecule of triacontane?

Draw an acceptable structure for 4-tert-butyloctane.

By using the appropriate molecular formulas, write a balanced equation which describes the complete combustion of nonane.

Structure and Bonding

Acids and Bases; Functional Groups

The Study of Chemical Reactions

Stereochemistry

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

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