Deck 4: Reactions of Alkenes and Alkynes

Question 1

What alkene would you use to prepare the following alkyl halide?

Answer 1

Only one alkene would be possible:

Question 2

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate:

Answer 2

Question 3

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases.
Predict.

Answer 3

Question 4

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases.
Predict.

Question 5

Instructions: The reaction of 2-methylpropene with HBr in ether gives one of the two products below. Answer the following question(s) about this reaction. Refer to instructions. Which product is the Markovnikov product?

Question 6

Predict the major organic product(s) in the reaction below. If more than one major organic product is expected, draw each one.

Question 7

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 8

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 9

The product(s) of the reaction when carried out in an organic solvent would be:

A) cis-1,2-dibromocyclohexane only
B) trans-1,2-dibromocyclohexane only
C) 50/50 mixture of cis-1,2-dibromocyclohexane and trans-1,2-dibromocyclohexane only
D) mixture with > 50% being trans-1,2-dibromocyclohexane only

Question 10

The following reaction is carried out in cyclohexane with the application of heat. Write the complete equation for the reaction below. If more than one major organic product is expected, draw each one.

Question 11

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 12

Predict the major organic product(s) in the reaction below. If more than one major organic product is expected, draw each one. Explain the significance of "35 $\degree$ C" and "ether" shown in the reaction.

Question 13

Alkene chemistry is dominated by what type of reaction?

A) substitution
B) electrophilic addition
C) nucleophilic addition
D) elimination
E) both b and c

Question 14

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases.
Predict:

Question 15

Instructions: To answer the question(s) below, consider the following reaction:
When cyclohexene reacts with chlorine in tetrachloromethane, the following dihalide is formed. Refer to instructions. Since the two chlorine atoms add to opposite faces of the cyclohexene double bond, we say that the reaction occurs with:

A) syn stereochemistry
B) cis stereochemistry
C) anti stereochemistry
D) retention of stereochemistry

Question 16

Instructions: To answer the question(s) below, consider the following reaction:
When cyclohexene reacts with chlorine in tetrachloromethane, the following dihalide is formed. Refer to instructions. Provide the IUPAC name for the product of this reaction.

Question 17

Instructions: The reaction of 2-methylpropene with HBr in ether gives one of the two products below. Answer the following question(s) about this reaction. Refer to instructions. The reaction mixture would contain a majority of which isomeric product?

Question 18

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 19

Predict the major product of the following reaction.

Question 20

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases.
Predict.

Question 21

Circle whichever of the following would be classified as a conjugated diene.

Question 22

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 23

MATCH each definition to the term it describes. Place the letter of the term in the blank to the left of the definition.
A. Cahn-Ingold-Prelog Rules
B. Markovnikov's Rule
Refer to Instructions. _____Assigns priorities to substituent groups on a carbon.

Question 24

What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?

A) carbocation
B) carbanion
C) radical
D) cyclic bromonium ion

Question 25

On the structures provided, draw arrows showing the electron flow in the reaction mechanism for the electrophilic addition of hydrogen bromide to hex-1-yne.

Question 26

What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide?

A) nucleophilic addition
B) electrophilic addition
C) radical addition
D) elimination

Question 27

Draw the structure of the monomer used to prepare the polymer shown below.

Question 28

What type of reactive intermediate is involved in both of the following general reaction types? 1) reaction of an alkene with $Br_2$ in the presence of water to give a bromohydrin
2) two-step hydroxylation of an alkene

A) carbocation
B) carbanion
C) radical
D) cyclic bromonium ion
E) cyclic ion

Question 29

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 30

MATCH each definition to the term it describes. Place the letter of the term in the blank to the left of the definition.
A. Cahn-Ingold-Prelog Rules
B. Markovnikov's Rule
Refer to Instructions. _____Predicts that in electrophilic additions to alkenes the more stable carbocation intermediate is formed.

Question 31

MATCH each definition to the term it describes. Place the letter of the term in the blank to the left of the definition.
A. Cahn-Ingold-Prelog Rules
B. Markovnikov's Rule
Refer to Instructions. _____Predicts that in addition of HX to alkenes, the H adds to the less substituted alkene carbon and the X adds to the more substituted alkene carbon.

Question 32

To answer the questions below, consider the following information:
In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: C₇H₁₂. Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO₄, gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO₄. Refer to Instructions. Suggest structures for A and
B.

Question 33

Draw the structure of the polymer formed from the monomer given below, showing four repeating units.

Question 34

Draw all the isomeric products formed from the addition of HCl to the following compound.

Question 35

Complete the following reaction

Question 36

Draw two resonance structures for the species below.

Question 37

Draw two resonance structures for the species below.

Question 38

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
Predict and indicate.

Question 39

What type of reaction mechanism accounts for the reaction of an alkyne with HBr to give an alkyl bromide?

A) nucleophilic addition
B) electrophilic addition
C) radical addition
D) elimination

Question 40

What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an alcohol?

A) carbocation
B) carbanion
C) radical
D) carbene

Question 41

Povidone is produced commercially as a series of products having mean molecular weights ranging from about 10,000 to 700,000. Complexed with iodine, povidone yields an iodophor, marketed under the tradename Betadine, which is used as a topical anti-infective. Identify the monomer unit(s) in povidone.

Question 42

To answer the questions below, consider the following information:
In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: C₇H₁₂. Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO₄, gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO₄. What was the other product formed in the KMnO₄ oxidation of B?