Deck 4: Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Question 1

An IUPAC name for is:

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

Answer 1

4-Isopropyl-2,5-dimethylheptane

Question 2

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

Answer 2

tert-Pentyl

Question 3

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

Answer 3

3-Methyl-5-(1-methylethyl)octane

Question 4

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 5

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 6

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 7

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 the above

Question 8

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

Question 9

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

Question 10

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 11

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

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

Question 12

An IUPAC name for the group is:

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

Question 13

The correct IUPAC name for is:

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 14

How many constitutional isomers are possible for the formula C₆H₁₄?

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

Question 15

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 16

An IUPAC name for the following compound is:

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 17

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 18

Isopentyl is the common name for which alkyl group?

A)

B)

C)

D)

E)

Question 19

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 20

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 21

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 22

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 23

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 24

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 25

Which compound is a bicycloheptane?

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

Question 26

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 27

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 28

Which of the above is bicyclo[4.3.0]nonane?

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

Question 29

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 30

Which of the following is bicyclo[3.2.2]nonane?

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

Question 31

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 32

The correct IUPAC name for the following compound is:

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 33

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 34

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 35

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 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

Which of the above is bicyclo[3.3.1]nonane?

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

Question 38

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

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

Question 39

Which of the above is bicyclo[5.2.0]nonane?

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

Question 40

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 41

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 42

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 the above

Question 43

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 44

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) All but one above
E) All the above

Question 45

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 46

Which is the most stable conformation of cyclohexane?

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

Question 47

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 the above are true

Question 48

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 49

The most stable conformation of butane is:

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

Question 50

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 51

The least stable conformation of butane is:

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

Question 52

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

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

Question 53

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 54

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 55

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 56

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 57

Which cycloalkane has the greatest ring strain?

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

Question 58

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 59

The least stable conformation of cyclohexane is the:

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

Question 60

The least stable conformation of butane is:

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

Question 61

Which conformation represents the most stable conformation of trans-1-bromo-4-methylcyclohexane?

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

Question 62

The most stable conformation of cis-1-tert-butyl-2-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 twist boat conformation is adopted.

Question 63

The most stable conformation of trans-1-tert-butyl-2-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 is in the half chair conformation.

Question 64

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

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

Question 65

How many moles of hydrogen (H₂)will react with 3-cyclobutylpropan-1-ol?

A) 1
2
B) 2
C) 3
D) 4
E) None of the above

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

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

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

Question 68

Catalytic hydrogenation of which of the following will yield 2-methylpentane?

A) 2-methyl-1-pentene
2
B) 2-methyl-2-pentene
C) 4-methyl-2-pentene
D) 4-methyl-1-pentene
E) All of the above

Question 69

In the most stable conformation of cis-1,4-dimethylcyclohexane,the methyl groups are:

A) one axial,one equatorial.
B) both axial.
C) both equatorial.
D) alternating between being both axial and both equatorial.
E) None of the above

Question 70

Which of these C₁₀H₁₈ isomers is predicted to be the most stable?

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

Question 71

Which of the following will have the same energy after undergoing ring flip?

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

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

Question 73

How many moles of hydrogen (H₂)will react with (trans,trans)-hepta-3,5-dien-1-yne?

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

Question 74

The most stable conformation of trans-1-tert-butyl-3-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 twist boat conformation is adopted.

Question 75

cis-1,3-Dibromocyclohexane is represented by structure(s):

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

Question 76

Which of the following can be described as trans isomers?

A) I
B) II,V
C) III,IV
D) I,III and IV
E) None of the above are trans isomers.

Question 77

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

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

Question 78

Select the reagents necessary to convert cyclopentene into cyclopentane.

A) H₂ and Ni
B) H₂O
C) Heat
D) Zn,H₃O⁺
E) Light

Question 79

Which alkene would yield 3-methylpentane when subjected to catalytic hydrogenation?

A)

B)

C)

D)

E)

Question 80

Which of the following can be described as cis isomers?

A) I
B) II,V
C) III,IV
D) I,III and IV
E) None of the above are cis isomers.