Deck 14: Electrophilic Addition to Nonpolar Π Bonds 2: Reactions Involving Cyclic Transition States

Question 1

What reagent is required to complete the following reaction?

A)CH₂N₂
B)NaOH
C)HCl
D)PCl₃
E)Cl₂

Answer 1

NaOH

Question 2

When a carbene reacts with an alkene,what functionality is created?

A)Cyclopropane ring
B)Oxetane
C)Epoxide
D)Alkyne
E)Alcohol

Answer 2

Cyclopropane ring

Question 3

Carbenes react with alkenes utilizing which fundamental step?

A)Nucleophilic addition
B)Electrophilic addition
C)Nucleophile elimination
D)Electrophile elimination
E)S_N2

Answer 3

Electrophilic addition

Question 4

What is the product of the following reaction?

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

Question 5

What is the product of the following reaction?

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

Question 6

Carbenes are routinely created using alkenes plus which of the following molecules?

A)CH₂N₂
B)CH₂Cl₂
C)CH₂Br₂
D)All of the above (a-c)
E)None of the above

Question 7

Which fundamental step can be found in the mechanism for the following reaction?

A)Homolysis
B)Heterolysis
C)Electrophilic elimination
D)Nucleophilic addition
E)Carbocation rearrangement

Question 8

Which of the following is true about using oxymercuration-reduction to add an OH to an alkene?

A)The mechanism is susceptible to carbocation rearrangements.
B)The mechanism proceeds through a mercurinium ion intermediate.
C)Only terminal alkenes can be used as starting materials.
D)The mechanism proceeds using anti-Markovnikov addition.
E)Reduction with NaBH₄ is stereoselective.

Question 9

What is the product of the following reaction?

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

Question 10

Which of the following is true regarding carbenes?

A)They are unreactive in halogenated solvents.
B)They can be used to create epoxides.
C)They are charged species.
D)They need to be generated in situ.
E)They are highly nucleophilic.

Question 11

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of II and III

Question 12

What is the product of the following reaction?

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

Question 13

What is the product of the following reaction?

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

Question 14

What reagent(s)will complete the following reaction?

A)I
B)II
C)III
D)IV
E)Both III and IV will work.

Question 15

When the alkene below is treated with Br₂ and H₂O,which is true about the stereochemistry of the product?

A)A single enantiomer will be produced.
B)A racemic mixture will result.
C)A mixture of diastereomers will be produced.
D)A single diastereomer will be produced.
E)A meso compound will be produced.

Question 16

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of III and IV

Question 17

When an alkene is treated with Cl₂,which of the following is not a part of the mechanism?

A)An electrophilic addition step.
B)An S_N2 step.
C)The creation of a product with two anti Cl atoms.
D)A homolysis step.
E)The creation of a bromonium ion intermediate.

Question 18

When the alkene below is treated with Br₂,which is true about the stereochemistry of the product?

A)A pair of enantiomers will be produced.
B)A single diastereomer will be produced.
C)A mixture of diastereomers will be produced.
D)A meso compound will be produced.
E)The product will be achiral.

Question 19

What starting material is required to complete the following transformation?

A)I
B)II
C)III
D)IV
E)Both III and IV are acceptable starting materials.

Question 20

What is the product of the following reaction?

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

Question 21

Draw the detailed mechanism and the product for the following reaction.

Question 22

What reagent is required to complete the following reaction?

Question 23

What reagent(s)will complete the following reaction?

A)I
B)II
C)III
D)IV
E)Both I and III will work.

Question 24

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of III and IV

Question 25

What is the product of the following reaction?

Question 26

Identify the reagent(s)required to synthesize the following racemic halohydrin.

Question 27

What reagent(s)will complete the following reaction?

A)I
B)II
C)III
D)IV
E)Both I and III will work.

Question 28

The following alkene is treated with Br₂.What is the stereochemical relationship of the two bromine atoms in the product?

Question 29

What is the formal charge on a carbene?

Question 30

What reagent best completes the following reaction?

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

Question 31

Which of the following reactions will produce the highest yield?

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

Question 32

What is the product of the following set of reactions?

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

Question 33

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of III and IV

Question 34

Draw the detailed mechanism and the product for the following reaction.Be sure to include stereochemistry,if applicable.

Question 35

What is the product of the following reaction?

Question 36

Show how the following molecule can be synthesized from an alkene.

Question 37

What is the product of the following reaction?

Question 38

What is the product of the following reaction?

Question 39

A carbon atom that possesses two bonds and a lone pair of electrons is called a ________.

Question 40

Which fundamental step does not occur in the mechanism for the reaction below?

A)Nucleophilic addition
B)Nucleophile elimination
C)Heterolysis
D)Coordination
E)Proton transfer

Question 41

Draw the product for the following reaction.

Question 42

Give two ways to synthesize an epoxide starting with the given alkene.Which one is more efficient? Explain.

Question 43

Draw the correct starting material for the reaction below.

Question 44

What is the product of the following reaction?

Question 45

Show the reagent(s)required to complete the following reaction.

Question 46

Supply the three missing products.

Question 47

Identify missing compounds A,B,and C.

Question 48

Draw the alkene that can be epoxidized using mCPBA to yield the following compound.

Question 49

Draw the product of the following reaction.

Question 50

Provide the reagents needed to complete the following reaction.

Question 51

What is the product of the following reaction.

Question 52

What is the product of the following reaction?

Question 53

Draw the products of the following reactions.

Question 54

Show how the following compound can be synthesized from an alkene.

Question 55

Name the reagent(s)required to complete the following reaction.