Deck 8: Alkenes: Structure and Preparation Via Elimination Reactions

Question 1

Drawn below is the structure of Singulair® (montelukast), a medication used to manage athsma. What is the degree of substitution of the alkene of Singulair®?

A) Monosubstituted
B) Disubstituted
C) Trisubstituted
D) Tetrasubstituted

Answer 1

Disubstituted

Question 2

Is the geometry of the following alkene E, Z, or neither?

Answer 2

E

Question 3

Is the geometry of the following alkene E, Z, or neither?

Answer 3

Z

Question 4

What is the degree of substitution of the following alkene?

A) Monosubstituted
B) Disubstituted
C) Trisubstituted
D) Tetrasubstituted

Question 5

Provide an IUPAC name for the following compound.

Question 6

Provide an IUPAC name for the following compound.

Question 7

Which of the following is the correct structure of 4-methylcyclopentene?

A)
B)
C)
D)

Question 8

Which of the following is the IUPAC name for the following compound?

A) 2-ethyl-1,1,3-trimethylbutene
B) 3-ethyl-2,4-dimethyl-2-pentene
C) 2,4-dimethylhexene
D) 4-ethyl-1,3-dimethyl-3-pentene

Question 9

Draw the structure of 2,3-dimethyl-1-pentene.

Question 10

What is the degree of substitution of the following alkene?

A) Monosubstituted
B) Disubstituted
C) Trisubstituted
D) Tetrasubstituted

Question 11

What is the degree of substitution of the following alkene?

A) Monosubstituted
B) Disubstituted
C) Trisubstituted
D) Tetrasubstituted

Question 12

Provide an IUPAC name for the following compound.

Question 13

Provide an IUPAC name for the following compound.

Question 14

Draw the E isomer of 2-methyl-3-heptene.

Question 15

Is the geometry of the following alkene E, Z, or neither?

Question 16

Which of the following is the correct structure of 2-methyl-1-butene?

A)
B)
C)
D)

Question 17

Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. What is the degree of substitution of the alkene of Crestor®?

A) Monosubstituted
B) Disubstituted
C) Trisubstituted
D) Tetrasubstituted

Question 18

Draw the structure of 3-methylcyclopentene.

Question 19

Is the geometry of the following alkene E, Z, or neither?

Question 20

Which of the following is the IUPAC name for the following compound?

A) 1-methyl-2-cyclohexene
B) 2-methylcyclohexene
C) 3-methylcyclohexene
D) 1-methyl-5-cyclohexene

Question 21

Draw the major product of the following elimination.

Question 22

Which of the following would be the best base for performing the following elimination?

A)
B)
C)
D)

Question 23

Show the mechanism for the following elimination, assuming that it is a concerted reaction.

Question 24

Which of the following shows a mechanism of a concerted elimination?

A)
B)
C)
D)

Question 25

Which of the following is the major product of the following elimination?

A)
B)
C)

Question 26

Draw the Z isomer of 3,4-dimethyl-3-hexene.

Question 27

Draw the E isomer of 3,4-dimethyl-3-hexene.

Question 28

Rank the following from most to least stable.

A)
B)
C)
D)

Question 29

Rank the following from most to least stable.

A) A, B, C
B) C, B, A
C) B, C, A
D) B, A, C

Question 30

What would be the best base for performing the following elimination?

Question 31

What is the product of the following elimination?

Question 32

Rank the following from most to least stable.

A)
B)
C)

Question 33

Which of the following is the most reactive in an E2 reaction?

A)
B)
C)

Question 34

Given the following alkane, draw the least stable alkene isomer with the same basic skeleton.

Question 35

Viridenomycin, shown below, is a polyene antibiotic that displays anti-tumor activity. Its structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, how many disubstituted Z alkenes are present in viridenomycin?

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

Question 36

Which of the following is the major product of the following elimination?

A)
B)
C)

Question 37

Which of the following alkenes is more stable?

A)
B)

Question 38

Show the mechanism for the following elimination, assuming that it is a concerted reaction.

Question 39

What is the product of the following elimination?

Question 40

Show the mechanism for the following elimination, assuming that it is a concerted reaction.

Question 41

Draw the major product of the following reaction.

Question 42

Which of the following is most reactive in an E1 reaction?

A)
B)
C)

Question 43

Draw the major product of the following reaction.

Question 44

Draw the major product of the following reaction.

Question 45

Draw the major product of the following reaction.

Question 46

What is the product of the following elimination?

Question 47

Draw the isomer of 2-bromo-1,1,3-trimethylcyclohexane that would be more reactive in an E2 elimination.

Question 48

Draw the major product of the following elimination.

Question 49

Which of the following alkyl halides would be more reactive in an E2 elimination?

A)
B)

Question 50

Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

Question 51

Draw the major product of the following reaction.

Question 52

Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

A)
B)
C)
D)

Question 53

Draw the major product of the following reaction.

Question 54

Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

Question 55

Which of the following is most reactive in an E1 reaction?

A)
B)
C)

Question 56

Draw the major product of the following reaction.

Question 57

Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

A)
B)
C)
D)

Question 58

Draw the major product of the following reaction.

Question 59

Draw the major product of the following reaction.

Question 60

Draw the major product of the following reaction.

Question 61

Which of the following is the energy diagram for the following reaction?

A)
B)
C)
D)

Question 62

Draw the mechanism and product for the following elimination, without using rearrangement.

Question 63

Will the following alcohol be likely to undergo rearrangement during a dehydration reaction?

Question 64

What is the structure of a rearranged carbocation that does not have a four-membered ring in the following acid-catalyzed dehydration of the following compound?

Question 65

Will the following alcohol undergo rearrangement during a dehydration reaction?

Question 66

Draw the mechanism for the following dehydration.

Question 67

Draw the mechanism and product for the following elimination.

Question 68

Draw the product of the following dehydration reaction.

Question 69

What is the structure of the rearranged carbocation intermediate in the following dehydration?

Question 70

What is the first step of the following dehydration?

A)
B)
C)
D)

Question 71

What are the steps of arrow pushing involved in the following mechanism?

Question 72

Which of the following is the structure of the rearranged carbocation intermediate in the following dehydration?

A)
B)
C)
D)

Question 73

For the following dehydration, draw the structure of the intermediate carbocation.

Question 74

Draw the product of the following dehydration reaction.

Question 75

Draw the major organic product of the following dehydration reaction.

Question 76

Draw the mechanism for the following dehydration.

Question 77

Which pattern of arrow pushing is associated with the first step in any dehydration reaction?

Question 78

For the following dehydration, draw the structure of the intermediate carbocation.

Question 79

For the following dehydration, draw the structure of the intermediate carbocation.

Question 80

Draw an energy diagram for the following reaction, assuming that it is exothermic.