Deck 4: Nomenclature and Conformations of Alkanes and Cycloalkanes

Question 1

The neopentyl group has the alternative name:

A)1,1-Dimethylpropyl
B)1,2-Dimethylpropyl
C)2,2-Dimethylpropyl
D)1-Methylbutyl
E)2-Methylbutyl

Answer 1

2,2-Dimethylpropyl

Question 2

An IUPAC name for the group is:

A)Isopentyl
B)Isoamyl
C)sec-Butylmethyl
D)2-Methylbutyl
E)2-Ethylpropyl

Answer 2

2-Methylbutyl

Question 3

What is the common name for this compound?

A)Isobutyl bromide
B)tert-Butyl bromide
C)Butyl bromide
D)sec-Butyl bromide
E)Bromo-sec-butane

Answer 3

Isobutyl bromide

Question 4

Provide a name for the following compound:

A)4-Isobutyl-3,4-dimethylheptane
B)4-sec-Butyl-2,4-dimethylheptane
C)2,4,5-Trimethyl-4-propylheptane
D)3,4,6-Trimethyl-4-propylheptane
E)4-Isobutyl-4,5-dimethylheptane

Question 5

Neglecting stereochemistry,which of these common group names is ambiguous,i.e.,does not refer to one specific group?

A)Butyl
B)sec-Butyl
C)tert-Pentyl
D)Neopentyl
E)sec-Pentyl

Question 6

A correct IUPAC name for the following compound is:

A)2,5-Dimethyl-3-propylheptane
B)3,6-Dimethyl-5-propylheptane
C)6-Methyl-4-(1-methylethyl)octane
D)2-Methyl-3-(2-methylbutyl)hexane
E)3-Methyl-5-(1-methylethyl)octane

Question 7

How many constitutional isomers are possible for the formula C₆H₁₄?

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

Question 8

The IUPAC name for is:

A)6-Ethyl-3,4-dimethylheptane
B)2-Ethyl-4,5-dimethylheptane
C)3,4,6-Trimethyloctane
D)3,5,6-Trimethyloctane
E)2-(1-Methylpropyl)-4-methylhexane

Question 9

How many compounds with the formula C₇H₁₆ (heptanes)contain a single 3° carbon atom?

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

Question 10

How many alkanes of formula C₇H₁₆ possess a quaternary carbon atom?

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

Question 11

How many compounds with the formula C₄H₁₁N contain a 2^o amine and a single 2^o carbon atom?

A)0
B)1
C)2
D)3
E)4

Question 12

An IUPAC name for is:

A)5-Methyl-4-(1-methylpropyl)hexane
B)2-Methyl-3-(1-methylpropyl)hexane
C)2-Methyl-3-(2-methylpropyl)hexane
D)3-Methyl-4-(1-methylethyl)heptane
E)5-Methyl-4-(1-methylethyl)heptane

Question 13

Which of the following pairs of compounds represent pairs of constitutional isomers?

A)2-Methylbutane and pentane
B)2-Chlorohexane and 3-chlorohexane
C)sec-Butyl bromide and tert-butyl bromide
D)Propyl chloride and isopropyl chloride
E)All of these choices.

Question 14

What is the correct IUPAC name for the following compound?

A)3-Hydroxymethylheptane
B)3-Hydroxymethylhexane
C)3-Methyloxyheptane
D)2-Ethyl-1-hexanol
E)2-Ethyl-1-heptanol

Question 15

What is a correct name for the following compound?

A)3-Isobutyl-2-methylheptane
B)3-sec-Butyl-2-methyloctane
C)5-Isobutyl-6-methylheptane
D)2-Ethyl-3-isopropyloctane
E)4-Isopropyl-3-methylnonane

Question 16

Isopentyl is the common name for which alkyl group?

A)
B)
C)
D)
E)

Question 17

Provide a name for the following compound:

A)3-Isobutyl-2,4-dimethylhexane
B)3-sec-Butyl-2,5-dimethylhexane
C)4-sec-Butyl-2,5-dimethylhexane
D)4-Isopropyl-2,5-dimethylheptane
E)4-Isopropyl-3,6-dimethylheptane

Question 18

Which of these is the common name for the 1,1-dimethylpropyl group?

A)tert-Butyl
B)tert-Pentyl
C)Isopentyl
D)Neopentyl
E)sec-Pentyl

Question 19

What is the simplest alkane,i.e.,the one with the smallest molecular weight,which possesses primary,secondary and tertiary carbon atoms?

A)2-Methylpropane
B)2-Methylbutane
C)2-Methylpentane
D)3-Methylpentane
E)2,2-Dimethylbutane

Question 20

Provide a name for the following compound:

A)2-Bromo-4-chloro-4-isopropylpentane
B)4-Bromo-2-chloro-2-isopropylpentane
C)5-Bromo-3-chloro-2,3-dimethylhexane
D)2-Bromo-4-chloro-4,5-dimethylhexane
E)2-(2-Bromopropyl)-2-chloro-3-methylbutane

Question 21

The correct IUPAC name for the following compound is:

A)5-(1-pentanolyl)-cyclobutane
B)5-cyclobutyl-1-pentanol
C)1-cyclobutyl-5-pentanol
D)1-(5-pentanolyl)-cyclobutane
E)none of these choices

Question 22

Which of the following structures represents bicyclo[3.2.1]octane?

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

Question 23

Which of the following is bicyclo[4.3.0]nonane?

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

Question 24

Which compound is a bicycloheptane?

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

Question 25

Which of the following is bicyclo[3.2.2]nonane?

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

Question 26

What is the correct name of the following compound?

A)1-Chlorobicyclo[4.1.1]octane
B)2-Chlorobicyclo[4.1.0]octane
C)2-Chlorobicyclo[4.1.1]octane
D)2-Chlorobicyclo[4.1.1]heptane
E)5-Chlorobicyclo[4.1.1]octane

Question 27

What is the correct IUPAC name for the following compound?

A)5-Ethyl-3-methylhexanol
B)5-Ethyl-3-methyl-1-hexanol
C)2-Ethyl-4-methyl-6-hexanol
D)3,5-Dimethyl-7-heptanol
E)3,5-Dimethyl-1-heptanol

Question 28

Provide a name for the following compound:

A)1-Hydroxy-3-sec-butylcyclopentane
B)3-sec-Butyl-1-cyclopentanol
C)1-sec-Butyl-3-cyclopentanol
D)4-sec-Butyl-1-cyclopentanol
E)3-Isobutyl-1-cyclopentanol

Question 29

A correct name for the following compound is:

A)7,7-dichlorobicyclo[2.2.1]heptane
B)2,2-dichlorobicyclo[1.2.2]heptane
C)1,1-dichlorobicyclo[2.2.1]heptane
D)1,1-dichlorobicyclo[1.2.2]heptane
E)None of these choices

Question 30

Which is the correct name for the compound shown below?

A)Bicyclo[2.2.0]hexane
B)Bicyclo[2.2.0]butane
C)Bicyclo[2.2.2]hexane
D)Bicyclo[2.2.1]hexane
E)Disquarane

Question 31

What is the correct IUPAC name for the following compound?

A)5-Ethyl-3-fluorohexanol
B)5-Ethyl-3-fluoro-1-hexanol
C)2-Ethyl-4-fluoro-6-hexanol
D)3-Fluoro-5-methyl-7-heptanol
E)3-Fluoro-5-methyl-1-heptanol

Question 32

Which of the following is bicyclo[5.2.0]nonane?

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

Question 33

Which of the following is a correct name which corresponds to the common name tert-pentyl alcohol?

A)2,2-Dimethyl-1-propanol
B)2-Ethyl-2-propanol
C)2-Methyl-2-butanol
D)3-Methyl-1-butanol
E)Methyl tert-butanol

Question 34

The correct IUPAC name for the following compound is:

A)1-methyl-2-ethyl-3-cyclopropanol
B)2-methyl-3-ethyl-1-cyclopropanol
C)3-ethyl-2-methyl-1-cyclopropanol
D)1-ethyl-2-methyl-3-cyclopropanol
E)none of these choices

Question 35

A correct name for the following compound is:

A)4-bromo-3,8-dimethylbicyclo[5.2.2]nonane
B)3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane
C)4-bromo-3,8-dimethylbicyclo[5.2.1]decane
D)7-bromo-2,6-dimethylbicyclo[5.2.0]nonane
E)4-bromo-3,8-dimethylbicyclo[5.2.0]nonane

Question 36

A correct name for the following compound is:

A)2-Methylbicyclo[4.3.0]nonane
B)1-Methylbicyclo[4.3.1]nonane
C)7-Methylbicyclo[4.3.0]nonane
D)2-Methylbicyclo[4.3.1]nonane
E)1-Methylbicyclo[4.3.0]nonane

Question 37

A correct IUPAC name for the following compound is:

A)4-propyl-5-chloro-3-heptanol
B)4-propyl-3-chloro-5-heptanol
C)4-(1-chloropropyl)-3-heptanol
D)5-chloro-4-propyl-3-heptanol
E)3-hydroxy-4-propyl-5-chloroheptane

Question 38

What is the name of this compound?

A)Bicyclo[2.2.2]octane
B)Bicyclo[3.2.1]octane
C)Bicyclo[4.1.1]octane
D)Bicyclo[4.2.0]octane
E)Bicyclo[3.3.0]octane

Question 39

A correct name for the following compound is:

A)3-Chloro-8-methylbicyclo[4.3.0]nonane
B)8-Methyl-3-chlorobicyclo[4.3.1]nonane
C)3-Methyl-7-chlorobicyclo[4.3.0]nonane
D)3-Methyl-7-chlorobicyclo[4.3.1]decane
E)3-Chloro-8-methyl[4.3.0]bicyclononane

Question 40

Which of the following is bicyclo[3.3.1]nonane?

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

Question 41

The least stable conformation of 3-bromo-2-methylpentane,viewed through the C-3-C-4 bond (i.e.,C-3 in the front,C-4 in the back):

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

Question 42

Give the IUPAC name for

A)3-Methyl-4-hexyne
B)4-Methyl-2-hexyne
C)2-Ethyl-3-pentyne
D)4-Ethyl-2-pentyne
E)3-Methyl-2-hexyne

Question 43

The most stable conformation of 1,2-dibromoethane is:

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

Question 44

The least stable conformation of butane is:

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

Question 45

Which staggered Newman projection(s),looking down the C-2-C-3 bond (C-2 in front and C-3 in back),illustrates the following boxed compound?

A)I,II and V
B)II and V
C)III and IV
D)V only
E)None of these choices.

Question 46

Which staggered Newman projection(s),looking down the C-2-C-3 bond (C-2 in front and C-3 in back),illustrate(s)the following boxed compound?

A)I only
B)II and V
C)I and II
D)III only
E)None of these choices.

Question 47

Which staggered Newman projection(s),looking down the C-3-C-4 bond (C-3 in front and C-4 in back),illustrate(s)the following boxed compound?

A)I,II and III
B)II and V
C)I and II
D)III only
E)None of these choices.

Question 48

Consider the graph below,which is a plot of the relative energies of the various conformations of 2,3-dimethylbutane,viewed through the C-2-C-3 bond.The conformations corresponding to the 120^o and 240^o are:

A)eclipsed,more stable than the conformation at 0^o
B)eclipsed,more stable than the conformation at 180^o
C)staggered,more stable than the conformation at 0^o
D)staggered,less stable than the conformation at 180^o
E)two of these choices are true

Question 49

The most stable conformation of 2,3-dibromobutane,viewed through the C-2-C-3 bond :

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

Question 50

Which conformation(s)of 1,2-dibromoethane does not illustrate one or more gauche interactions?

A)I and II only
B)II,III,and V only
C)I,III,and IV only
D)II and III only
E)All these choices

Question 51

A correct IUPAC name for the following compound is:

A)3,6,7-trimethyl-4-bromo-1-octene
B)4-bromo-3-methyl-6-isopropyl-1-heptene
C)4-bromo-3,6,7-trimethyl-1-octene
D)4-bromo-6-isopropyl-3-methyl-1-heptene
E)4-bromo-6-isopropyl-3,6-dimethyl-1-hexene

Question 52

Consider the graph below,which is a plot of the relative energies of the various conformations of hexane,viewed through the C-2-C-3 bond.The conformations corresponding to the 60^o and 300^o are:

A)eclipsed
B)staggered and gauche
C)staggered and anti
D)more stable than the conformation at 180^o
E)none of these choices

Question 53

The most stable conformation of butane is:

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

Question 54

Which staggered Newman projection(s),looking down the C-2-C-3 bond (C-2 in front and C-3 in back),illustrates the following boxed compound?

A)I,II and III
B)II and V
C)I and II
D)V only
E)None of these choices.

Question 55

What is the correct IUPAC name for the following compound?

A)trans-3-Hydroxymethyl-2-heptene
B)trans-2-(1-methylethyl)-4-hexen-1-ol
C)trans-5-(1-methylethyl)-2-hexen-6-ol
D)cis-5-isopropyl-2,6-hexenol
E)cis-2-(1-methylethyl)-4-hepten-1-ol

Question 56

The IUPAC name for diisobutylacetylene is

A)2,7-Dimethyl-4-octene
B)2,7-Dimethyl-4-octyne
C)3,6-Dimethyl-4-octyne
D)2,5-Diethyl-3-hexyne
E)2,2,5,5-Tetramethyl-3-hexyne

Question 57

The graph below is a plot of the relative energies of the various conformations of:

A)Ethane
B)Propane
C)Chloroethane
D)1-Chloropropane (C1-C2 rotation)
E)Butane (C1-C2 rotation)

Question 58

Which conformation(s)show(s)the bromines in a gauche orientation for 2,3-dibromobutane,viewed through the C-2-C-3 bond?

A)I and II only
B)III and IV only
C)I and V only
D)II only
E)None of these choices.

Question 59

The most stable conformation of 3-bromo-2-methylpentane,viewed through the C-3-C-4 bond (i.e.,C-3 in the front,C-4 in the back):

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

Question 60

Give the IUPAC name for

A)trans-2-methyl-3-hepten-5-yne
B)trans-6-methyl-4-hepten-2-yne
C)cis-2-methyl-3-hepten-5-yne
D)cis-6-methyl-4-hepten-2-yne
E)none of these choices

Question 61

The most stable conformation for 1,2-ethanediol (ethylene glycol)is shown below.It is the most stable conformation because

A)this corresponds to an anti conformation.
B)in general,gauche conformations possess the minimum energy.
C)it is stabilized by intramolecular hydrogen bonding.
D)it is a staggered conformation.
E)it has the highest energy of all the possibilities.

Question 62

cis-1,2-Dibromocyclohexane is represented by structure(s):

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

Question 63

The least stable conformation of 2,3-dimethylpentane,viewed through the C-2-C-3 bond (i.e.,C-2 in the front,C-3 in the back):

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

Question 64

Select the systematic name for

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

Question 65

Which cycloalkane has the least ring strain?

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

Question 66

What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane?

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

Question 67

trans-1,2-Dibromocyclohexane is represented by structure(s):

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

Question 68

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

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

Question 69

Which is the most stable conformation of cyclohexane?

A)Chair
B)Twist
C)Boat
D)Half-chair
E)Staggered

Question 70

The most stable conformation of 3-bromo-2-methylpentane,viewed through the C-2-C-3 bond (i.e.,C-2 in the front,C-3 in the back):

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

Question 71

The graph below is a plot of the relative energies of the various conformations of:

A)2-chloropropane
B)1,3-dichloropropane
C)2-methylpropane
D)Butane (C1-C2 rotation)
E)Butane (C2-C3 rotation)

Question 72

The twist boat conformation is the preferred conformation for this compound.

A)cis-1,4-Di-tert-butylcyclohexane
B)trans-1,4-Di-tert-butylcyclohexane
C)cis-1,3-Di-tert-butylcyclohexane
D)trans-1,2-Di-tert-butylcyclohexane
E)None of these choices.

Question 73

What is the most thermodynamically stable chair conformation for the substituents on cis-4-tert-butylcyclohexanol?

A)both groups equatorial
B)both groups axial
C)tert-butyl group equatorial and OH group axial
D)tert-butyl group axial and OH group equatorial
E)a boat conformation is adopted due to steric strain

Question 74

Which cycloalkane has the greatest ring strain?

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

Question 75

Which of the following is a conformer of trans-1,2-diethylcyclohexane?

A)I and II
B)I,II and III
C)I and IV
D)all of these choices
E)none of these choices

Question 76

The least stable conformation of 3-bromo-2-methylpentane,viewed through the C-2-C-3 bond (i.e.,C-2 in the front,C-3 in the back):

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

Question 77

The least stable conformation of cyclohexane is the

A)boat.
B)twist boat.
C)chair.
D)half-chair.
E)twist chair.

Question 78

What is the name of the IUPAC name of the following compound?

A)trans-4-chlorocyclohexan-1-ol
B)cis-1-chlorocyclohexan-4-ol
C)trans-4-chlorocyclohexanol
D)cis-4-chlorocyclohexanol
E)none of these choices

Question 79

The most stable conformation of 2,3-dimethylpentane,viewed through the C-2-C-3 bond (i.e.,C-2 in the front,C-3 in the back):

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

Question 80

Select the structure for cis-3-methyl-6-vinylcyclohexene.

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