Deck 2: Alkanes and Cycloalkanes

Question 1

The IUPAC name for the following molecule is:

A) 2-chloro-3-ethyl-6,6-dimethylheptane
B) 6-chloro-5-ethyl-2,2-dimethylheptane
C) 6-chloro-2,2-dimethyl-5-ethylheptane
D) 2,2-dimethyl-5-chloroethylheptane
E) 6-chloro-5-ethyl-2-dimethylheptane

Answer 1

6-chloro-5-ethyl-2,2-dimethylheptane

Question 2

The name of the alkyl group that contains three carbons is:

A) methyl
B) ethyl
C) propyl
D) isopropyl
E) none of these

Answer 2

propyl

Question 3

What statement does NOT apply to the boiling points of alkanes?

A) The boiling point increases as the length of the carbon chain increases.
B) Straight chain alkanes have a higher boiling point than their branched isomers.
C) Because they are nonpolar, alkanes have lower boiling points than other organic compounds of similar molar mass.
D) The boiling points are affected by Van der Waals attractions.
E) The boiling points are influenced by hydrogen bonding.

Answer 3

The boiling points are influenced by hydrogen bonding.

Question 4

What is the molecular formula of an alkane that has fourteen carbon atoms?

A) C₁₄H₂₈
B) C₁₄H₃₀
C) C₁₄H₃₂
D) C₁₄H₃₄
E) C₁₄H₂₆

Question 5

What is the molecular formula of a cycloalkane that has six carbon atoms?

A) C₆H₁₂
B) C₆H₁₄
C) C₆H₁₆
D) C₆H₁₀
E) C₆H₇

Question 6

The structural formula for 2,2,3-trimethylhexane is

A)
B)
C)
D)
E)

Question 7

What is a correct name for the following molecule?

A) 2,2-dichlorocyclopropane
B) 1,1-dichlorocyclopentane
C) 1,1-dichloropropane
D) trans-1,1-dichlorocyclopropane
E) 1,1-dichlorocyclopropane

Question 8

What is the correct name for the following cycloalkane?

A) bromoethylcyclohexane
B) trans-1-ethyl-3-bromocyclohexane
C) cis-3-bromo-1-ethylhexane
D) 1-bromo-3-ethylcyclohexane
E) cis-1-bromo-3-ethylcyclohexane

Question 9

The IUPAC name for the following molecule is:

A) 2-ethyl-4-methylpentane
B) 4-methyl-2-methylpentane
C) 2,4-dimethylhexane
D) 1-isopropyl-2-methylbutane
E) 2,4-methylhexane

Question 10

Which of the following would exhibit hydrogen bonding?

A) CH₃Cl
B) CH₃OH
C) CH₄
D) CH₂Cl₂
E) CH₃CH₃

Question 11

Which of the following alkanes would have the highest boiling point?

A) pentane
B) 2-methylbutane
C) 2,2-dimethylpropane
D) hexane
E) 2-methylpentane

Question 12

What is the common name for the following molecule?

A) isobutyl bromide
B) tert-butyl bromide
C) butyl bromide
D) sec-butyl bromide
E) bromo-sec-butane

Question 13

The name of the alkyl group below is:

A) ethyl
B) propyl
C) isopropyl
D) butyl
E) isobutyl

Question 14

What is the name of the alkane that has three carbon atoms?

A) methane
B) ethane
C) propane
D) butane
E) isobutane

Question 15

The correct IUPAC name for (CH₃)₂CHCH(CH₃)(CH₂)₃CH(CH₃)₂ is

A) diisopropylpentane.
B) 1,1,2,6,6-pentamethylhexane.
C) 2,5-diisopropylpentane.
D) 2,3,7-trimethyloctane.
E) 1,4-diisopropylpentane.

Question 16

The correct IUPAC name for is:

A) 1,3,3-trimethylcyclobutane.
B) cis-1,3,3-trimethylcyclobutane.
C) trans-1,3,3-trimethylcyclobutane.
D) 1,1,3-trimethylcyclobutane.
E) 2,2,4-trimethylcyclobutane.

Question 17

Which of the following structures is 2-methylpentane?

A)
B)
C)
D)
E)

Question 18

What is the IUPAC name for the following compound?

A) isohexyl bromide
B) 3-bromo-4-methylpentane
C) 1-bromopropylpropane
D) 3-bromo-2-methylpentane
E) 2-methyl-3-bromopentane

Question 19

Trans-1-bromo-3-methylcyclobutane is represented by which structure below?

A)
B)
C)
D)
E)

Question 20

The correct IUPAC name for the following molecule is:

A) 6-ethyl-3,4,-dimethylheptane
B) 2-ethyl-4,5-dimethylheptane
C) 3,4,6-trimethyloctane
D) 3,5,6-trimethyloctane
E) none of these

Question 21

The preferred conformation of butane is given by which of the following Newman projection formulas?

A)
B)
C)
D)
E)

Question 22

The boiling points of normal alkanes

A) rise as the length of the carbon chain increases.
B) rise as the length of the carbon chain decreases.
C) are higher than the boiling points of branched alkanes with the same molecular formula.
D) a and c
E) b and c

Question 23

The compounds represented by the structures below are:

A) structural isomers.
B) different compounds.
C) cis-trans isomers.
D) conformers.
E) constitutional isomers.

Question 24

Cycloalkanes with __________ or more carbons in the ring are nonplanar.

A) 2
B) 3
C) 4
D) 5
E) 6

Question 25

The compounds represented by the structures below are:

A) constitutional isomers.
B) identical.
C) cis-trans isomers.
D) conformers.
E) different compounds (not isomers)..

Question 26

How many isomeric dichloro products can be obtained from the chlorination of cyclopropane?

A) 1
B) 2
C) 3
D) 4
E) 5

Question 27

For the most stable conformation of cis-1,3-dimethylcyclohexane:

A) both methyls will occupy the axial position
B) both methyls will occupy the equatorial position
C) one methyl will occupy the axial position and the other an equatorial position
D) more than one answer is correct

Question 28

The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which:

A) the t-butyl group is axial and the methyl group is equatorial
B) both groups are axial
C) both groups are equatorial
D) the methyl group is axial and the t-butyl group is equatorial
E) molecule exists in a boat conformation

Question 29

Which of the following pairs are examples of conformational isomerism?

A) chair and boat forms of cyclohexane
B) 1-iodopropane and 2-iodopropane
C) sec-butyl chloride and butyl iodide
D) cis and trans-1,2-dimethylcyclohexane
E) all of these

Question 30

How many monobromo products can be obtained from the bromination of cyclopentane?

A) 1
B) 2
C) 3
D) 4
E) 5

Question 31

The least stable conformation of butane is given by which of the following Newman projections?

A)
B)
C)
D)
E)

Question 32

The most stable conformation of propane is:

A) staggered
B) chair
C) planar
D) eclipsed
E) boat

Question 33

The compounds represented by the structures below are:

A) structural isomers.
B) different compounds.
C) cis-trans isomers.
D) conformers.
E) constitutional isomers.

Question 34

The least stable conformation of propane is:

A) staggered
B) chair
C) planar
D) eclipsed
E) boat

Question 35

Consider this chair conformation: When the ring flips,

A) the bromine becomes axial and the methyls become equatorial.
B) all three substituents become equatorial.
C) the bromine becomes equatorial and the methyls become axial.
D) the ring opens up.
E) one methyl becomes axial, one becomes equatorial, and the bromine becomes equatorial.

Question 36

In the chlorination of methane, the propagation steps involve forming:

A) H radicals
B) methyl radicals
C) chlorine radicals
D) a, b, and c
E) b and c

Question 37

The bond angle of a normal, tetrahedral, sp³ hybridized carbon is 109.5°.What is the C-C-C bond angle of cyclobutane?

A) 60°
B) 90°
C) 109.5°
D) 120°
E) 180°

Question 38

Consider this chair conformation:

A) The methyl and bromine are cis and the chlorine and bromine are cis.
B) The methyl and bromine are trans and the chlorine and bromine are cis.
C) The methyl and chlorine are trans and the methyl and bromine are cis.
D) The methyl and chlorine are trans and the methyl and bromine are trans.
E) The methyl and chlorine are trans and the bromine and chlorine are cis.

Question 39

The compounds represented by the structures below are:

A) structural isomers.
B) identical.
C) cis-trans isomers.
D) conformers.
E) constitutional isomers.

Question 40

Which cycloalkane has the highest boiling point?

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

Question 41

The number of possible dichlorination products of propane is

A) 2
B) 3
C) 4
D) 5
E) 6

Question 42

The number of possible dibromination products of 2-methylpropane is

A) 2
B) 3
C) 4
D) 5
E) 6

Question 43

The number of possible monobromination products, including cis-trans isomers, of methylcyclopentane is

A) 2
B) 3
C) 4
D) 5
E) 6