Question 1

Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene?

Accepted Answer

A)  cyclopropane < cyclobutane < cyclohexane < cyclopentane 
B)  cyclohexane < cyclopentane < cyclobutane < cyclopropane 
C)  cyclohexane < cyclobutane < cyclopentane < cyclopropane 
D)  cyclopentane < cyclopropane < cyclobutane < cyclohexane 
E)  cyclopropane < cyclopentane < cyclobutane < cyclohexane 
A)  cyclopropane < cyclobutane < cyclohexane < cyclopentane 
B)  cyclohexane < cyclopentane < cyclobutane < cyclopropane 
C)  cyclohexane < cyclobutane < cyclopentane < cyclopropane 
D)  cyclopentane < cyclopropane < cyclobutane < cyclohexane 
E)  cyclopropane < cyclopentane < cyclobutane < cyclohexane

Question 2

Identify the correct IUPAC name for each compound shown below.

Accepted Answer

A)  2-bromo-3-sec-butyl-4-ethylhexane 
B)  2-bromo-4-ethyl-3-sec-butylhexane 
C)  3-(1-bromoethyl)-2,4-diethylhexane 
D)  4-(1-bromoethyl)-3-ethyl-5-methylheptane 
E)  4-(1-bromoethyl)-5-ethyl-3-methylheptane 
A)  2-bromo-3-sec-butyl-4-ethylhexane 
B)  2-bromo-4-ethyl-3-sec-butylhexane 
C)  3-(1-bromoethyl)-2,4-diethylhexane 
D)  4-(1-bromoethyl)-3-ethyl-5-methylheptane 
E)  4-(1-bromoethyl)-5-ethyl-3-methylheptane

Question 3

Which of the following types of hydrocarbons is(are) saturated?

Accepted Answer

A)  alkanes 
B)  alkenes 
C)  alkynes 
D)  aromatics 
E)  All of the above are saturated. 
A)  alkanes 
B)  alkenes 
C)  alkynes 
D)  aromatics 
E)  All of the above are saturated.

Question 4

Without any change in conformation, translate the Newman projection shown below to a perspective structure.

Accepted Answer

The answer of Without any change in conformation, translate the...

Question 5

Provide the name of the compound below.

Accepted Answer

2,3,6,7-te

Question 6

Why are alkanes described as hydrophobic?

Accepted Answer

Alkanes are nonpolar

Question 7

Provide an acceptable name for the alkane shown below.

Accepted Answer

3-ethyl-4,

Question 8

How many methyl groups are present in 2,4-dimethylhexane?

Accepted Answer

A)  0 
B)  2 
C)  4 
D)  6 
E)  8 
A)  0 
B)  2 
C)  4 
D)  6 
E)  8

Question 9

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 10

Which of the following correctly lists the conformations of cis-1,4-di-t-butylcylcohexane in order of increasing energy?

Accepted Answer

A)  chair < boat < twist boat < half-chair 
B)  twist boat < boat < chair < half-chair 
C)  chair < twist boat < half-chair < boat 
D)  boat < chair < twisted boat < half-chair 
E)  half-chair < chair < boat < twisted boat 
A)  chair < boat < twist boat < half-chair 
B)  twist boat < boat < chair < half-chair 
C)  chair < twist boat < half-chair < boat 
D)  boat < chair < twisted boat < half-chair 
E)  half-chair < chair < boat < twisted boat

Question 11

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

Accepted Answer

C₆H₁₂ + 9 O₂ →

Question 12

Name the following compound and use the appropriate cis/trans designation.

Accepted Answer

trans - 1-

Question 13

Draw the most stable conformation of cis-1-ethyl-3-methylcyclohexane.

Accepted Answer

The answer of Draw the most stable conformation of cis-1-ethyl-3-methylcyclohexane....

Question 14

________ is the reaction process through which long-chain alkanes are converted into a mixture of short-chain alkanes and alkenes.

Accepted Answer

The answer of ________ is the reaction process through which...

Question 15

Identify the correct IUPAC name for the following structures.

Accepted Answer

A)  4-(2-iodo-1-methylethyl)-3-methylheptane 
B)  3-s-butyl-1-iodo-2-methylhexane 
C)  1-iodo-2,4-dimethyl-3-propylhexane 
D)  2,4-dimethyl-1-iodo-3-propylhexane 
A)  4-(2-iodo-1-methylethyl)-3-methylheptane 
B)  3-s-butyl-1-iodo-2-methylhexane 
C)  1-iodo-2,4-dimethyl-3-propylhexane 
D)  2,4-dimethyl-1-iodo-3-propylhexane

Question 16

Which line angle drawing best represents the Newman Projection shown below?

Accepted Answer

A)    
B)    
C)    
D)    
A)    
B)    
C)    
D)

Question 17

Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He).

Accepted Answer

Question 18

Draw the most stable conformation of cis-1-ethyl-4-isopropylcyclohexane.

Accepted Answer

The answer of Draw the most stable conformation of cis-1-ethyl-4-isopropylcyclohexane....

Question 19

Which of the following statements is a correct description of the most stable conformation of 1,1,3-trimethylcyclohexane?

Accepted Answer

A)  The methyl group at C-3 is equatorial. 
B)  C-1 is a tertiary carbon and C-3 is a primary carbon. 
C)  C-1 is a quaternary carbon and C-3 is a secondary carbon. 
D)  C-1 is a tertiary carbon and C-3 is a secondary carbon. 
E)  Both methyl groups at C-1 are equatorial. 
A)  The methyl group at C-3 is equatorial. 
B)  C-1 is a tertiary carbon and C-3 is a primary carbon. 
C)  C-1 is a quaternary carbon and C-3 is a secondary carbon. 
D)  C-1 is a tertiary carbon and C-3 is a secondary carbon. 
E)  Both methyl groups at C-1 are equatorial.

Question 20

Which of the following is a bridged bicyclic alkane?

Accepted Answer

A)  cis-decalin 
B)  bicyclo[2.2.1]heptane 
C)  bicyclo[3.2.0]heptane 
D)  bicyclo[4.1.0]heptane 
E)  none of the above 
A)  cis-decalin 
B)  bicyclo[2.2.1]heptane 
C)  bicyclo[3.2.0]heptane 
D)  bicyclo[4.1.0]heptane 
E)  none of the above

Exam 3: Structure and Stereochemistry of Alkanes

Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene?

Identify the correct IUPAC name for each compound shown below.

Which of the following types of hydrocarbons is(are) saturated?

Without any change in conformation, translate the Newman projection shown below to a perspective structure.

Provide the name of the compound below.

Why are alkanes described as hydrophobic?

Provide an acceptable name for the alkane shown below.

How many methyl groups are present in 2,4-dimethylhexane?

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

Which of the following correctly lists the conformations of cis-1,4-di-t-butylcylcohexane in order of increasing energy?

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

Name the following compound and use the appropriate cis/trans designation.

Draw the most stable conformation of cis-1-ethyl-3-methylcyclohexane.

________ is the reaction process through which long-chain alkanes are converted into a mixture of short-chain alkanes and alkenes.

Identify the correct IUPAC name for the following structures.

Which line angle drawing best represents the Newman Projection shown below?

Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He).

Draw the most stable conformation of cis-1-ethyl-4-isopropylcyclohexane.

Which of the following statements is a correct description of the most stable conformation of 1,1,3-trimethylcyclohexane?

Which of the following is a bridged bicyclic alkane?

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

Filters

Draw the chair conformer of cyclohexane. Label the axial hydrogens (H_a) and the equatorial hydrogens (H_e).