Deck 4: Alkanes and Cycloalkanes

Question 1

What is the IUPAC name of the following compound?

Answer 1

5-sec-butyl-4-ethyl-3-methylnonane

Question 2

What is the structure of [2.2.2]bicyclooctane?

Answer 2

Question 3

What is the IUPAC name of the following compound?

A) 2,3,5-triethylhexane
B) 2,4,5-triethylhexane
C) 2,4-diethyl-5-methylheptane
D) 4-ethyl-3,6-dimethyloctane

Answer 3

4-ethyl-3,6-dimethyloctane

Question 4

What is the parent chain of the following compound?

Question 5

What is the structure of 3-ethyl-2,4,6-trimethyloctane?

Question 6

What is the IUPAC name of the following compound?

Question 7

What is the IUPAC name of the following compound?

A) 1-ethyl-2-methylcyclohexane
B) 2-ethyl-1-methylcyclohexane
C) 1-ethyl-2-methylhexane
D) cyclononane

Question 8

What is the parent chain of the following compound?

A) octane
B) hexane
C) heptane
D) decane

Question 9

What is the IUPAC name of the following compound?

Question 10

What is the structure of an isopropyl group?

Question 11

What is the IUPAC name of the following compound?

Question 12

What is the IUPAC name of the following compound?

A) 2,5-diethylhexane
B) 3,6-dimethyloctane
C) 2-ethyl-5-methylheptane
D) 2,5-dimethylheptane

Question 13

What is the structure of 3-ethyl-3-methylpentane?

Question 14

What is the IUPAC name of the following compound?

Question 15

What is the IUPAC name of the following compound?

A) 3-isopropyl-5-ethylheptane
B) 2-methyl-3-ethyl-5-ethylheptane
C) 3,5-diethyl-2-methylheptane
D) 2-methyl-3,5-diethylheptane

Question 16

What is the common name of the following substituent?

A) isopropyl
B) tert-butyl
C) isobutyl
D) sec-butyl

Question 17

Which of the following is a tert-butyl group?

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

Question 18

What is the name of the parent chain of the following compound?

Question 19

What is the IUPAC name of the following compound?

Question 20

What is the parent chain of the following compound?

A) hexane
B) heptane
C) octane
D) nonane

Question 21

The process that converts straight-chain alkanes into branched hydrocarbons is called _____________.

A) hydrogenation
B) cracking
C) reforming
D) hydrolysis

Question 22

Give the structures and IUPAC names of all constitutional isomers of C₆H₁₄.

Question 23

What is the relationship between the following two compounds?

A) constitutional isomers
B) identical compounds
C) completely different and not constitutional isomers

Question 24

What is the correct stoichiometry of oxygen for the balanced redox reaction?

Question 25

Identify the size of the hydrocarbon that is used in gasoline.

A) C₁ - C₄
B) C₅ - C₁₂
C) C₁₂ - C₁₈
D) C₁₂ and higher

Question 26

The reaction shown below is an example of

A) catalytic cracking
B) thermal cracking
C) catalytic reforming
D) thermal reforming

Question 27

Complete the following combustion reaction, assuming that only CO₂ and H₂O are formed.

Question 28

What is the correct stoichiometry of oxygen for the balanced redox reaction?

Question 29

Which pair of the following compounds are constitutional isomers?

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

Question 30

Identify the size of the hydrocarbon that is used in natural gas.

A) C₁ - C₄
B) C₅ - C₁₂
C) C₁₂ - C₁₈
D) C₁₂ and higher

Question 31

What is the structure of 1-cyclopropyl-3-methylcyclopentane?

Question 32

What is the relationship between the following two compounds?

A) constitutional isomers
B) identical compounds
C) completely different and not constitutional isomers

Question 33

Complete the following combustion reaction, assuming that only CO₂ and H₂O are formed.

Question 34

Which of the following compounds are constitutional isomers?

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

Question 35

What is the relationship between the following two compounds?

A) constitutional isomers
B) identical compounds
C) completely different and not constitutional isomers

Question 36

Of the following isomers of C₉H₂₀, which is the most stable?

A) nonane
B) 3-methyloctane
C) 2,2-dimethylheptane
D) 2,2,3,4-tetramethylpentane

Question 37

What is the relationship between the following two compounds?

A) constitutional isomers
B) identical compounds
C) completely different and not constitutional isomers

Question 38

Which pair of the following compounds are constitutional isomers?

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

Question 39

What is the IUPAC name of the following compound?

Question 40

What is the relationship between the following two compounds?

A) constitutional isomers
B) identical compounds
C) completely different and not constitutional isomers

Question 41

Which of the following is a Newman projection of an eclipsed conformation for propane?

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

Question 42

Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

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

Question 43

Draw an energy diagram for the conformational analysis of propane.

Question 44

Draw a Newman projection for the following compound as viewed down the indicated bond in the conformation shown.

Question 45

Draw the wedge and dash structure of the following Newman projection.

Question 46

Which of the following is a Newman projection of a staggered conformation for ethane?

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

Question 47

Which of the following is a Newman projection of a staggered conformation for propane?

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

Question 48

Draw a wedge and dash structure of the following Newman projection.

Question 49

Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

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

Question 50

Which of the following is a wedge and dash structure for the following Newman projection?

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

Question 51

Draw a Newman projection of the following compound as viewed down the indicated bond in the conformation shown.

Question 52

Which of the following is a wedge and dash structure for the following Newman projection?

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

Question 53

Which of the following is a Newman projection of an eclipsed conformation for ethane?

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

Question 54

Identify the size of the hydrocarbon that is used in asphalt.

A) C₁ - C₄
B) C₅ - C₁₂
C) C₁₂ - C₁₈
D) C₁₂ and higher

Question 55

What is the eclipsing cost of Br and H if the energy difference between the staggered and eclipsed conformations of bromoethane is 13 kJ/mol?

Question 56

Draw a wedge and dash structure of the following Newman projection.

Question 57

Identify the size of the hydrocarbon that is used in jet fuel.

A) C₁ - C₄
B) C₅ - C₁₂
C) C₁₂ - C₁₈
D) C₁₂ and higher

Question 58

Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

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

Question 59

Which of the following is a wedge and dash structure for the following Newman projection?

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

Question 60

Draw a Newman projection for the following compound as viewed down the indicated bond in the conformation shown.

Question 61

Which of the following is a boat conformation of cyclohexane?

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

Question 62

Draw a chair conformation of methylcyclohexane.

Question 63

Which of the following is the highest energy conformer of the following compound?

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

Question 64

Which of the following cycloalkanes has the least angle strain?

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

Question 65

Which of the following is a chair conformation of the following substituted cyclohexane?

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

Question 66

Which of the following is a chair conformation of cyclohexane?

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

Question 67

Which of the following is the highest energy conformer of the following compound looking down the indicated bond?

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

Question 68

Draw the lowest energy conformer of the following compound as a Newman projection looking down the C2-C3 bond.

Question 69

Which of the following is a CH₃-CH₃ eclipsed conformation for butane?

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

Question 70

Which of the following is an anti conformation for butane?

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

Question 71

Draw the gauche conformer of the following compound looking down the indicated bond.

Question 72

Which of the following is a gauche conformation for butane?

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

Question 73

Which of the following is the highest energy conformer of the following compound?

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

Question 74

Which of the following is a CH₃-H eclipsed conformation for butane?

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

Question 75

Which of the following cycloalkanes has the most angle strain?

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

Question 76

Draw an energy diagram for rotation around the indicated bond of the following compound.

Question 77

What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol?

Question 78

Draw the Newman projection of the conformer of the following compound where the two methyl groups are anti.

Question 79

Draw the lowest energy conformer of the following compound as a Newman projection looking down the C2-C3 bond.

Question 80

Which of the following is the lowest energy conformer of the following compound looking down the indicated bond?

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