Deck 11: Organometallic Compounds

Question 1

Provide the major organic product of the following reactions.

Answer 1

Question 2

Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.

Answer 2

Question 3

Provide the structure of the major organic product that results when 1-bromocyclohexene reacts with metallic magnesium in diethyl ether.

Answer 3

Question 4

How would one use a Grignard-based synthesis to accomplish the following transformation?
benzyl bromide (PhCH₂Br)to 3-phenyl-1-propanol

Question 5

Provide the major organic product of the following reaction.

Question 6

What is the product of the following reaction?

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

Question 7

Provide the reagents necessary to accomplish the following transformation.

Question 8

What is the product of the following reaction?

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

Question 9

Which of the following sequences of reactions would be best when converting cyclohexene oxide into propylcyclohexane?

A)1)CH₃CCNa 2.H₃O⁺
B)1)CH₃CH₂CH₂MgBr 2.H₂SO₄,Δ 3.H₂,Pt
C)1)H₃O⁺ 2.CH₃CCNa
D)1)CH₃CH₂CH₂Li 2.HBr
E)1)H₃PO₄,Δ 2.CH₃CH₂CH₂MgBr 3.H⁺

Question 10

Which of the following is the strongest base?

A)HOMgBr
B)H₂O
C)CH₄
D)CH₃OH
E)CH₃MgBr

Question 11

Provide the major organic product of the following reaction.

Question 12

What is the product of the following reaction sequence?

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

Question 13

Provide the major organic product in the reaction below.

Question 14

Provide the major organic product of the following reaction.

Question 15

Provide the structure of the major organic product of the following reaction.

Question 16

Provide the major organic product of the following reactions.

Question 17

The following alkyl halide could not be used to form a Grignard reagent.Explain.
HO-CH₂CH₂-Br

Question 18

Show how the following synthesis could be carried out.

Question 19

Provide the major organic product of the following reaction.

Question 20

Provide the major organic product of the following reactions.

Question 21

Provide the major organic product of the reaction below.

Question 22

Provide the major organic product of the reaction below.

Question 23

Complete and balance the following reaction.
CH₃CH₂CH₂Li + CuI →

Question 24

Provide the major organic product of the reaction below.

Question 25

Provide the major organic product of the reaction below.

Question 26

Provide the major organic product of the following reactions.

Question 27

Complete and balance the following transmetallation reaction.
CH₃CH₂CH₂MgCl + SiCl₄ →

Question 28

Complete and balance the following transmetallation reaction.
CH₃CH₂CH₂MgCl + CdCl₂ →

Question 29

List the sequence of reagents necessary to prepare the appropriate Gilman reagent from ethyl iodide.

Question 30

What reagents are needed to accomplish the multistep transformation shown below?

Question 31

Provide the major organic product of the following reactions.

Question 32

Is an organolithium reagent more reactive than the comparable Grignard reagent or less reactive? Explain briefly.

Question 33

Provide the major organic product of the reaction below.

Question 34

Provide the major organic product of the reaction below.

Question 35

What reagents are needed to accomplish the multistep transformation shown below?

Question 36

Give the product of the following reaction.

Question 37

What is the major organic product of the following reaction sequence? CH₃C CCH₃

A)(E)-3-methyl-2-hexene
B)2-heptyne
C)5-decyne
D)(Z)-2-bromo-2-hexene
E)(E)-2-bromo-2-hexene

Question 38

What reagents are needed to accomplish the multistep transformation shown below?

Question 39

What reagents are needed to accomplish the multistep transformation shown below?

Question 40

Give the major organic product for the following reaction. CH₃CH₂BR + (CH₃CH₂CH₂)₂CuLi →

A)CH₃CH₂CH₂CH₂CH₂CH₃ + CH₃CH₂Cu
B)CH₃CH₂CH₂CH₂CH₃ + CH₃CH₂CH₂Cu
C)CH₃CH₂CH₂CH₂CH₂CH₃ + CH₃CH₂CH₂Cu
D)CH₃CH₂CH₂CH₂CH₂CH₃ + CH₃CH₂Li
E)CH₃CH₂CH₂CH₂CH₃ + CH₃CH₂CH₂Li

Question 41

Provide the major organic product of the reaction below.

Question 42

Name the organic products that would result from metathesis of 1,8-nonadiene.

Question 43

Give the major organic product for the following reaction.

Question 44

Give the major organic product for the following reaction.

Question 45

Give the major organic product for the following reaction.

Question 46

What two-word name is given to a reaction that breaks the carbon-carbon double bond and then rejoins the fragments with the double bonds forming in a different location?

Question 47

Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.

Question 48

Provide the structure of the alkene that will undergo metathesis to generate the compound below.

Question 49

Fill in the missing components in the reaction below.

Question 50

In a Grignard reagent,the carbon bonded to the magnesium has a partial ________ charge,because carbon is ________ electronegative than magnesium.This makes this carbon of the Grignard ________.

A)negative,more,nucleophilic
B)negative,less,electrophilic
C)positive,more,electrophilic
D)positive,less,nucleophilic
E)positive,less,electrophilic

Question 51

Provide the major organic product of the reaction below.

Question 52

Provide the major organic product of the reaction below.

Question 53

What type of intermediate is present when the Grubbs catalyst and a terminal alkene react?

A)metallocyclobutane
B)Grignard reagent
C)Gilman reagent
D)borate ester
E)permanganate ester

Question 54

Grignard reagents contain which of the following metals?

A)palladium
B)copper
C)magnesium
D)lithium
E)ruthenium

Question 55

Name the three major alkene products that result when 1-pentene is treated with Grubbs catalyst.

Question 56

Provide the major organic product of the reaction below.

Question 57

Provide the major organic product of the reaction below.

Question 58

Name the organic products that would result from metathesis of 2-methyl-1-pentene.

Question 59

Fill in the missing components in the reaction below.

Question 60

Provide the major organic product of the reaction below.

Question 61

In palladium catalyzed coupling reactions,the first step is called

A)oxidative elimination.
B)reductive addition.
C)oxidative addition.
D)reductive elimination.
E)none of the above.

Question 62

In palladium catalyzed coupling reactions,the last step is called

A)oxidative elimination.
B)reductive addition.
C)oxidative addition.
D)reductive elimination.
E)none of the above.

Question 63

In Suzuki and Heck reactions,the vinylic and aryl halides are used as substrates in the first step because they cannot undergo

A)substitution reaction.
B)β-elimination.
C)oxidative addition.
D)reductive elimination.
E)none of the above.

Question 64

Schrock catalysts are based on

A)palladium.
B)copper.
C)tungsten.
D)molybdenum.
E)C and D.

Question 65

Grubbs catalysts are based on

A)palladium.
B)copper.
C)magnesium.
D)lithium.
E)ruthenium.