Question 1

Which of the following cycloalkanes has the least angle strain?

Accepted Answer

A)  Cyclopropane 
B)  Cyclohexane 
C)  Cyclopentane 
D)  Cycloheptane 
A)  Cyclopropane 
B)  Cyclohexane 
C)  Cyclopentane 
D)  Cycloheptane

Question 2

Rank the conformers of butane in order of decreasing stability, putting the most stable first.

Accepted Answer

A)  IV > I > II > III 
B)  IV > I > III > II 
C)  II > III > I > IV 
D)  I > IV > II > III 
A)  IV > I > II > III 
B)  IV > I > III > II 
C)  II > III > I > IV 
D)  I > IV > II > III

Question 3

What is the IUPAC name for the following compound?

Accepted Answer

A)  3-Ethyl-2,7-dimethyl-5-sec-butyldecane 
B)  5-sec-Butyl-3-ethyl-2,7-dimethyldecane 
C)  2,7-Dimethyl-3-ethyl-5-sec-butyldecane 
D)  3-Ethyl-2,7-dimethyl-5-isobutyldecane 
A)  3-Ethyl-2,7-dimethyl-5-sec-butyldecane 
B)  5-sec-Butyl-3-ethyl-2,7-dimethyldecane 
C)  2,7-Dimethyl-3-ethyl-5-sec-butyldecane 
D)  3-Ethyl-2,7-dimethyl-5-isobutyldecane

Question 4

Which of the following compounds has only primary, secondary and tertiary carbon atoms?

Accepted Answer

A)  Pentane 
B)  2-Methylpentane 
C)  2,2-Dimethylpentane 
D)  2,2,3-Trimethylpentane 
A)  Pentane 
B)  2-Methylpentane 
C)  2,2-Dimethylpentane 
D)  2,2,3-Trimethylpentane

Question 5

What is the IUPAC name for the following compound?

Accepted Answer

A)  3-Ethyl-1-methylcyclohexane 
B)  1-Ethyl-3-methylcyclohexane 
C)  1-Ethyl-3-methylhexane 
D)  3-Ethyl-1-methylhexane 
A)  3-Ethyl-1-methylcyclohexane 
B)  1-Ethyl-3-methylcyclohexane 
C)  1-Ethyl-3-methylhexane 
D)  3-Ethyl-1-methylhexane

Question 6

Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting the most stable first.

Accepted Answer

A)  I > II > III > IV 
B)  III > II > IV > I 
C)  III > IV > II > I 
D)  I > II > IV > III 
A)  I > II > III > IV 
B)  III > II > IV > I 
C)  III > IV > II > I 
D)  I > II > IV > III

Question 7

Which of the following are anti conformers?

Accepted Answer

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

Question 8

Which of the following is the most stable conformation of cis-1-ethyl-3-isopropylcyclohexane?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 9

What is the IUPAC name for the following compound?

Accepted Answer

A)  1-Butylcyclohexane 
B)  Cyclohexanebutane 
C)  1-Cyclohexylbutane 
D)  Butylcyclohexane 
A)  1-Butylcyclohexane 
B)  Cyclohexanebutane 
C)  1-Cyclohexylbutane 
D)  Butylcyclohexane

Question 10

What is the IUPAC name for the following compound?

Accepted Answer

A)  3,5-Diethyl-6-methylheptane 
B)  3,5-Diethyl-2-methylheptane 
C)  3-Ethyl-5-isopropylheptane 
D)  5-Ethyl-3-isopropylheptane 
A)  3,5-Diethyl-6-methylheptane 
B)  3,5-Diethyl-2-methylheptane 
C)  3-Ethyl-5-isopropylheptane 
D)  5-Ethyl-3-isopropylheptane

Question 11

Which of the following is not another representation for 2-methylbutane?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 12

Which of the following conformers has the highest energy?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 13

Which of the following statements about the conformations of acyclic alkanes is true?

Accepted Answer

A)  Conformations are the same arrangements of atoms that cannot be interconverted by rotation about single bonds. 
B)  In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon. 
C)  In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon. 
D)  Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered conformation, and vice versa. 
A)  Conformations are the same arrangements of atoms that cannot be interconverted by rotation about single bonds. 
B)  In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon. 
C)  In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon. 
D)  Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered conformation, and vice versa.

Question 14

What is the approximate C-C-C bond angle in propane?

Accepted Answer

A)  90° 
B)  109.5° 
C)  120° 
D)  180° 
A)  90° 
B)  109.5° 
C)  120° 
D)  180°

Question 15

How many constitutional isomers are there with the molecular formula C5H12?

Accepted Answer

A)  2 
B)  3 
C)  4 
D)  5 
A)  2 
B)  3 
C)  4 
D)  5

Question 16

What is the IUPAC name for the following compound?

Accepted Answer

A)  5-Ethyl-3,6-dimethylheptane 
B)  3-Ethyl-2,5-dimethylheptane 
C)  3-Ethyl-2,5-dimethyloctane 
D)  5-Ethyl-3,6-dimethyloctane 
A)  5-Ethyl-3,6-dimethylheptane 
B)  3-Ethyl-2,5-dimethylheptane 
C)  3-Ethyl-2,5-dimethyloctane 
D)  5-Ethyl-3,6-dimethyloctane

Question 17

What is the IUPAC name for the following compound?

Accepted Answer

A)  1-Butyl-3-methylcyclohexane 
B)  1-sec-Butyl-3-methylcyclohexane 
C)  1-Methyl-3-sec-butylcyclohexane 
D)  1-sec-Butyl-3-methylhexane 
A)  1-Butyl-3-methylcyclohexane 
B)  1-sec-Butyl-3-methylcyclohexane 
C)  1-Methyl-3-sec-butylcyclohexane 
D)  1-sec-Butyl-3-methylhexane

Question 18

Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first.

Accepted Answer

A)  I > II > III 
B)  I > III > II 
C)  II > III > I 
D)  III > II > I 
A)  I > II > III 
B)  I > III > II 
C)  II > III > I 
D)  III > II > I

Question 19

Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first.

Accepted Answer

A)  I < III < II 
B)  I < II < III 
C)  II < III < I 
D)  III < II < I 
A)  I < III < II 
B)  I < II < III 
C)  II < III < I 
D)  III < II < I

Question 20

Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Exam 4: Alkanes

Which of the following cycloalkanes has the least angle strain?

Rank the conformers of butane in order of decreasing stability, putting the most stable first.

What is the IUPAC name for the following compound?

Which of the following compounds has only primary, secondary and tertiary carbon atoms?

What is the IUPAC name for the following compound?

Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting the most stable first.

Which of the following are anti conformers?

Which of the following is the most stable conformation of cis-1-ethyl-3-isopropylcyclohexane?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

Which of the following is not another representation for 2-methylbutane?

Which of the following conformers has the highest energy?

Which of the following statements about the conformations of acyclic alkanes is true?

What is the approximate C-C-C bond angle in propane?

How many constitutional isomers are there with the molecular formula C5H12?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first.

Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first.

Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

How many constitutional isomers are there with the molecular formula C₅H₁₂?