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

3

Question 2

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

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

Answer 2

1

Question 3

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

Answer 3

syn elimination

Question 4

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

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

Question 5

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 6

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 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 sequence of reactions?

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

Question 11

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

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

Question 12

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

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

Question 13

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 14

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

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

Question 15

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

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

Question 16

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

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

Question 17

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 18

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

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

Question 19

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

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

Question 20

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

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

Question 21

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

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

Question 22

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

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

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

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

Question 25

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

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

Question 26

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

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

Question 27

Which of the following is not a pericyclic reaction?

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

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 obtained from the following reaction?

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

Question 30

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

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

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

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

Which of the following is the least reactive dienophile?

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 compounds is the most reactive dienophile?

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

Question 40

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

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

Question 41

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

Question 42

Organopalladium compounds are particularly useful in forming biaryl compounds.

Question 43

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

Question 44

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

Question 45

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

Question 46

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 47

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

Question 48

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

Question 49

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

Question 50

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

Question 51

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

Question 52

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

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

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

Question 55

Cross-coupled reactions involve a transmetallation step.

Question 56

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

Question 57

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

Question 58

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

Question 59

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 60

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

Question 61

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

Question 62

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

Question 63

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

Question 64

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

Question 65

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

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 reaction?

Question 73

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

Question 74

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

Question 75

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

Question 76

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

Question 77

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