Deck 7: Alkenes: Structure and Reactivity

Question 1

Draw: (3E)-3,7-dimethyl-1,3,6-octatriene

Answer 1

Question 2

Exhibit 7-10
Consider the following reaction:
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Refer to Exhibit 7-10.Below are all the chemical structures and intermediates involved in this reaction.On the structures provided,show all electron flow using the arrow formalism for the complete stepwise mechanism for this reaction.
​

Answer 2

Question 3

Draw: 3,6-dimethyl-1,4-cyclohexadiene

Answer 3

Question 4

Rank the carbocations below in order of increasing stability (least stable = 1;most stable = 3).Place the number corresponding to the carbocation's relative stability in the blank below the structure.

Question 5

Exhibit 7-2
Dieldrin,C₁₂H₈Cl₆O,is a pentacyclic compound formerly used as an insecticide.
Refer to Exhibit 7-2.How many double bonds does dieldrin have?

Question 6

The original question was combined with #10.This placeholder question is here to maintain the integrity of the numbering system between the printed copy and ExamView.Therefore,it has been marked "do not use on test" in ExamView's question information dialog.As a result,this placeholder question is automatically prevented from being chosen as a test question.

Question 7

Write the complete stepwise mechanism for the following reaction.Show all intermediate structures and all electron flow with arrows.

Question 8

Arrange the following bicyclic alkenes in order of increasing stability (least stable to most stable).

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

Question 9

Exhibit 7-4
Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name:

Question 10

Exhibit 7-3
2-Pentene is an example of a disubstituted alkene.
​
CH₃CH=CHCH₂CH₃
Refer to Exhibit 7-3.

A)Draw the cis and trans isomers of 2-pentene and label them.
B)Circle the isomer which is most stable.

Question 11

Exhibit 7-9
Consider the following reaction:
​
Draw a qualitative reaction energy diagram for this reaction.Label the positions of all reactants,intermediates and products.

Question 12

Exhibit 7-2
Dieldrin,C₁₂H₈Cl₆O,is a pentacyclic compound formerly used as an insecticide.
Refer to Exhibit 7-2.Calculate the degree of unsaturation for Dieldrin.Show calculations for credit.

Question 13

Exhibit 7-4
Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name:

Question 14

Exhibit 7-13
The reaction of isobutene with HBr in ether gives one of the two products below as the major product.Answer the following question(s) about this reaction.
​
Refer to Exhibit 7-13.Which product would be the major product?

Question 15

Draw: cis-2-hexene

Question 16

Exhibit 7-10
Consider the following reaction:
​
Refer to Exhibit 7-10.Why does the rearrangement that results in the formation of product B occur?

Question 17

Draw: trans-4,4-dimethyl-2-pentene

Question 18

Exhibit 7-4
Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name:

Question 19

Exhibit 7-4
Provide names for each structure below.Be sure to include the cis,trans or E,Z designations where applicable.
Name:

Question 20

Exhibit 7-9
Consider the following reaction:
​
Write the complete stepwise mechanism for this reaction.Show all intermediate structures and show all electron flow using the curved arrow convention.

Question 21

Which of the following does not characterize a more highly substituted carbocation?

A)forms more rapidly than less highly substituted carbocations
B)forms product more rapidly than less highly substituted carbocations
C)has a larger ΔG^± than less highly substituted carbocations
D)is more stable than less highly substituted carbocations
E)All of these characterize a highly substituted carbocation.

Question 22

Exhibit 7-13
The reaction of isobutene with HBr in ether gives one of the two products below as the major product.Answer the following question(s) about this reaction.
​
Refer to Exhibit 7-13.Which product would have a higher energy transition state for the formation of the intermediate leading to it?

Question 23

Exhibit 7-13
The reaction of isobutene with HBr in ether gives one of the two products below as the major product.Answer the following question(s) about this reaction.
​
Refer to Exhibit 7-13.Which product would be formed via a primary carbocation?

Question 24

Examine the following biological reaction. In this reaction,which of the following is not indicated?

A)The reaction produces three products.
B)Isocitrate is the primary reactant.
C)Isocitrate dehydrogenase is the catalyst for the reaction,
D)NAD⁺ is an abbreviation for a required reactant.
E)All indicate the conditions of the reaction.

Question 25

If the following compound was dissolved in ether and treated with HBr,which of the following describes the major product(s) of the reaction?

A)
B)
C)
D)a mixture of and

Question 26

​Draw the mechanism of the electrophilic addition of HCl to 2-propene.

Question 27

Draw the mechanism of hydride shift in the reaction between 4-methyl-2-pentene and hydrochloric acid.​

Question 28

​Write the reaction mechanism of the electrophilic reaction of HI to 2-pentene.

Question 29

Examine the following reaction. Which of the following is not indicated by this representation?

A)KI is the solvent
B)Cyclohexene is the reactant of interest.
C)The reaction is carried out at room temperature.
D)The reaction occurs in solution.
E)All indicate the conditions of the reaction.

Question 30

Exhibit 7-13
The reaction of isobutene with HBr in ether gives one of the two products below as the major product.Answer the following question(s) about this reaction.
​
Refer to Exhibit 7-13.According to Hammond's Postulate,which product would have a transition state structure most closely resembling the carbocation intermediate?

Question 31

The following shows the connectivity of atoms only.Atoms other than carbon and hydrogen are labeled. How many degrees of unsaturation are present in the compound?

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

Question 32

Cyclohexanol (-OH bonded to cyclohexane) produces cyclohexene when heated to 70 °C in the presence of a sulfuric acid catalyst.Write the equation for the reaction showing only the reactant of interest and the conditions of the reaction

Question 33

Identify the isoprene units in limonene,an essential oil found in oil of lemon and orange.

Question 34

If the following compound were dissolved in ether and treated with HCl,which of the following describes the product(s) of the reaction?

A)3-bromoheptane
B)4-bromoheptane
C)a mixture of 3-bromoheptane and 4-bromoheptane

Question 35

Exhibit 7-13
The reaction of isobutene with HBr in ether gives one of the two products below as the major product.Answer the following question(s) about this reaction.
​
Refer to Exhibit 7-13.Which product would be formed by a carbocation experiencing the greatest degree of hyperconjugative stabilization?

Question 36

Exhibit 7-13
The reaction of isobutene with HBr in ether gives one of the two products below as the major product.Answer the following question(s) about this reaction.
​
Refer to Exhibit 7-13.Increasing the temperature at which the reaction is run would lead to an increase in the percentage of which product relative to the other product?

Question 37

Consider the following molecular model. I Which of the following could be used to synthesize this compound?

A)
B)
C)
D)Either or

E)Any of the above