Deck 24: Catalytic Carbon-Carbon Bond Formation

Question 1

What is the major organic product obtained from the following reaction?

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

Answer 1

1

Question 2

What is the major organic product obtained from the following reaction?

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

Answer 2

4

Question 3

What is the major organic product obtained from the following reaction?

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

Answer 3

4

Question 4

What is the major organic product obtained from the following reaction?

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

Question 5

What is the major organic product obtained from the following reaction?

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

Question 6

What is the major organic product obtained from the following reaction?

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

Question 7

What is the major organic product obtained from the following reaction?

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

Question 8

What is the major organic product obtained from the following reaction?

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

Question 9

What is the major organic product obtained from the following reaction?

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

Question 10

What is the major organic product obtained from the following reaction?

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

Question 11

Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

A) oxidative addition
B) syn addition
C) syn elimination
D) reductive elimination

Question 12

What is the major organic product obtained from the following reaction?

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

Question 13

What is the major organic product obtained from the following sequence of reactions?

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

Question 14

What is the major organic product obtained from the following reaction?

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

Question 15

Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

A) oxidative addition
B) syn addition
C) syn elimination
D) reductive elimination

Question 16

In the general reaction for the Suzuki coupling, which of the following does not serve as the leaving group "X"?

A) Br
B) I
C) OTf
D) CH₃

Question 17

What is the major organic product obtained from the following reaction?

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

Question 18

What is the major organic product obtained from the following reaction?

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

Question 19

Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

A) oxidative addition
B) syn addition
C) syn elimination
D) reductive elimination

Question 20

Which term describes the following mechanistic step in the catalytic cycle of the Heck reaction?

A) oxidative addition
B) syn addition
C) syn elimination
D) reductive elimination

Question 21

What is the major organic product of the following sequence of reactions?

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

Question 22

What is the major organic product obtained from the following reaction?

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

Question 23

What is the major organic product obtained from the following reaction?

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

Question 24

Which of the following is not a pericyclic reaction?

A) Cope rearrangement
B) Claisen rearrangement
C) Suzuki coupling
D) Diels-Alder reaction

Question 25

What is the major organic product obtained from the following reaction?

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

Question 26

Which of the following is the least reactive diene in Diels Alder reactions?

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

Question 27

Which diene can be used to prepare the following product by alkene metathesis?

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

Question 28

What is the major organic product obtained from the following reaction?

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

Question 29

What is the major organic product of the following sequence of reactions?

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

Question 30

Which of the following compounds is the most reactive dienophile?

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

Question 31

What is the major organic product obtained from the following reaction?

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

Question 32

What is the major organic product obtained from the following reaction?

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

Question 33

Which of the following is the least reactive diene in Diels Alder reactions?

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

Question 34

What is the major organic product obtained from the following reaction?

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

Question 35

What is the major organic product of the following sequence of reactions?

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

Question 36

What is the major organic product obtained from the following reaction?

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

Question 37

What is the major organic product obtained from the following reaction?

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

Question 38

What is the major organic product of the following sequence of reactions?

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

Question 39

Which of the following is the least reactive dienophile?

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

Question 40

What is the major organic product of the following sequence of reactions?

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

Question 41

Use the reaction types given below in answering the following questions relating to reaction conditions.
______involves the use of organoboron compounds.

A)Heck reaction
B)Stille coupling
C)Suzuki coupling
D)Sonogashira coupling
E)Alkene metathesis
Place the appropriate letter in the blank provided.

Question 42

Consider diorganocopper reagents and organopalladium compounds. Only the latter is useful in forming new carbon-to-carbon bonds

Question 43

Use the reaction types given below in answering the following questions relating to reaction conditions.
______involves the use of alkynyl complexes.

A)Heck reaction
B)Stille coupling
C)Suzuki coupling
D)Sonogashira coupling
E)Alkene metathesis
Place the appropriate letter in the blank provided.

Question 44

Consider the following reactants. This is an example of a Heck reaction.

Question 45

The following product is a simplified penicillin analog. When the reaction is carried out in the presence of a palladium catalyst the structure of the missing reactant is shown below.

Question 46

During oxidative addition, the coordination (number) of the metal ________ by two.

Question 47

The intermediate in a Heck reaction can be described as a tetrahedral Pd(II) species.

Question 48

Use the reaction types given below in answering the following questions relating to reaction conditions.
______involves the use of stannates.

A)Heck reaction
B)Stille coupling
C)Suzuki coupling
D)Sonogashira coupling
E)Alkene metathesis
Place the appropriate letter in the blank provided.

Question 49

In the Heck reaction, all reactants are required in stoichiometric amounts except the Pd(0) species.

Question 50

Use the reaction types given below in answering the following questions relating to reaction conditions.
______involves an interchange of alkenyl groups.

A)Heck reaction
B)Stille coupling
C)Suzuki coupling
D)Sonogashira coupling
E)Alkene metathesis
Place the appropriate letter in the blank provided.

Question 51

In the Heck reaction, polar aprotic solvents are generally used.

Question 52

In an alkene metathesis reaction where both alkenyl groups are in the same molecule, the product formed is a _______________.

Question 53

The following polymer segment can be produced using an olefinic metathesis reaction. To produce the polymer, the reaction is repeated many times. The name of the reactant is__________.

Question 54

Use the reaction types given below in answering the following questions relating to reaction conditions.
______involves the substitution of a vinylic hydrogen.

A)Heck reaction
B)Stille coupling
C)Suzuki coupling
D)Sonogashira coupling
E)Alkene metathesis
Place the appropriate letter in the blank provided.

Question 55

Which of the following terms describes the mechanism of a Diels-Alder reaction?

A) electrophilic addition
B) nucleophilic addition
C) pericyclic addition
D) conjugate addition

Question 56

In the Heck reaction, alkenes with large substituent groups are the most reactive.

Question 57

During oxidative addition and reductive elimination, the ionic charge of the metal changes.

Question 58

Consider the following reactants. The product of this reaction is shown below.

Question 59

Organopalladium compounds are particularly useful in forming biaryl compounds.

Question 60

Cross-coupled reactions involve a transmetallation step.

Question 61

What is the major organic product obtained from the following reaction?

Question 62

Identify "X" in the given reaction. ​

A)

B)

C)

D)

Question 63

What are the two major organic products obtained from the following reaction?

Question 64

What is the major organic product obtained from the following reaction?

Question 65

Identify "X" in the given reaction. ​

A)

B)

C)

D)

Question 66

What is the major organic product obtained from the following reaction?

Question 67

What is the major organic product obtained from the following reaction?

Question 68

What is the major organic product obtained from the following reaction?

Question 69

What is the major organic product obtained from the following reaction?

Question 70

What is the major organic product obtained from the following reaction?

Question 71

What is the major organic product obtained from the following reaction?

Question 72

What is the major organic product obtained from the following sequence of reactions?

Question 73

What is the major organic product obtained from the following reaction?

Question 74

What is the major organic product obtained from the following reaction?

Question 75

Identify "X" and "Y" in the given sequence of reactions. ​

A) X is
, and Y is
.
B) X is
, and Y is
.
C) X is
, and Y is
.
D) X is
, and Y is
.

Question 76

What is the major organic product obtained from the following reaction?

Question 77

What is the major organic product obtained from the following sequence of reactions?

Question 78

Provide descriptions for each of the mechanistic steps in the following Heck reaction.

Question 79

What is the major organic product obtained from the following reaction?

Question 80

What is the major organic product obtained from the following reaction?