Deck 12: Organometallic Compounds

Question 1

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

Answer 1

Question 2

Provide the major organic product of the following reactions.

Answer 2

Question 3

Provide the major organic product of the following reaction.

Answer 3

Question 4

Provide the major organic product in the reaction below.

Question 5

Provide the major organic product of the following reaction.

Question 6

Provide the major organic product of the following reactions.

Question 7

Provide the reagents necessary to accomplish the following transformation.

Question 8

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 9

Which of the following is the strongest base?

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

Question 10

Provide the major organic product of the following reactions.

Question 11

Provide the major organic product of the following reaction.

Question 12

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

Question 13

What is the product of the following reaction?

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

Question 14

What is the product of the following reaction sequence?

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

Question 15

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

Question 16

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

Question 17

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

Question 18

Provide the major organic product of the following reaction.

Question 19

Show how the following synthesis could be carried out.

Question 20

What is the product of the following reaction?

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

Question 21

Provide the major organic product of the following reactions.

Question 22

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

Question 23

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

Question 24

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

Question 25

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

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 26

Provide the major organic product of the reaction below.

Question 27

Provide the major organic product of the reaction below.

Question 28

Complete and balance the following reaction.
CH₃CH₂CH₂Li + CuI →

Question 29

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)

Question 30

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

Question 31

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

Question 32

Provide the major organic product of the reaction below.

Question 33

Provide the major organic product of the reaction below.

Question 34

Give the product of the following reaction.

Question 35

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

Question 36

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

Question 37

Provide the major organic product of the reaction below.

Question 38

Provide the major organic product of the reaction below.

Question 39

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

Question 40

Provide the major organic product of the following reactions.

Question 41

Provide the major organic product of the reaction below.

Question 42

Provide the major organic product of the reaction below.

Question 43

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

Question 44

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 45

Give the major organic product for the following reaction.

Question 46

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 47

Give the major organic product for the following reaction.

Question 48

Provide the major organic product of the reaction below.

Question 49

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

Question 50

Provide the major organic product of the reaction below.

Question 51

Provide the major organic product of the reaction below.

Question 52

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 53

Provide the major organic product of the reaction below.

Question 54

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

Question 55

Give the major organic product for the following reaction.

Question 56

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

Question 57

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