Deck 15: An Introduction to Organometallic Compounds

Question 1

Which of the following molecules are deprotonated by ethylmagnesium bromide?

A)phenol, PhOH
B)propyne, CH₃C $\equiv$ CH
C)dimethylamine, (CH₃)₂NH
D)all of these

Answer 1

all of these

Question 2

Which of the following is the best choice of solvent for the formation of phenyllithium by the reaction of bromobenzene with lithium?

A)water
B)ethanol
C)tetrahydrofuran
D)acetic acid

Answer 2

tetrahydrofuran

Question 3

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

A)2-pentanol
B)pentane
C)1-pentene
D)(E)-2-pentene

Answer 3

pentane

Question 4

Which combination(s) of alkyl bromide and epoxide can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide?

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

Question 5

Which of the following is the best choice of solvent for the formation of phenylmagnesium bromide by the reaction of bromobenzene with magnesium?

A)water
B)methanol
C)diethyl ether
D)acetic acid

Question 6

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

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

Question 7

Which of the following mechanisms accounts for the acid-base reaction of ethylmagnesum bromide with acetylene to give acetylide anion?

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

Question 8

Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide?

A)only 1 and 2
B)only 1 and 4
C)only 1, 2 and 3
D)only 2 and 4

Question 9

Which combination(s) of alkyl bromide and epoxide can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide?

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

Question 10

Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide?

A)only 1
B)only 1 and 2
C)only 1, 2 and 3
D)1, 2, 3 and 4

Question 11

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

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

Question 12

Which of the following compounds is the strongest base?

A)CH₃CH₂MgBr
B)CH₃CH₂OH
C)CH₃CH₂OMgBr
D)CH₃CH₃

Question 13

Which of the following bonds has the most ionic character?

A)C-Al
B)C-Hg
C)C-Mg
D)C-Zn

Question 14

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

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 term describes the process whereby an alkyl halide undergoes reaction with magnesium metal to give an alkylmagnesium bromide (Grignard reagent)?

A)nucleophilic substitution
B)electrophilic addition
C)oxidative addition
D)reductive elimination

Question 17

Which of the following compounds is the strongest base?

A)NaOH
B)NH₃
C)CH₃Li
D)CH₃OH

Question 18

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

A)2-methylbutane
B)3-methyl-1-butanol
C)3-methyl-2-butene
D)3-methyl-2-butanol

Question 19

What is the change in oxidation state of the metal when magnesium reacts with an alkyl bromide to give an alkylmagnesium bromide (Grignard reagent)?

A)0 $\rarr$ +1
B)0 $\rarr$ +2
C)0 $\rarr$ -1
D)0 $\rarr$ -2

Question 20

Which of the following bonds has the most ionic character?

A)C-Sn
B)C-Cu
C)C-Zn
D)C-Li

Question 21

Which of the following is not true regarding the carbon atom of the methylene carbene, H₂C: ?

A)it is sp² hybridized
B)it has a complete octet of valence electrons
C)it has a vacant 2p atomic orbital
D)it has a lone pair of electrons in an sp² molecular orbital

Question 22

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

A)2-methylheptane
B)3-methylheptane
C)2-methyloctane
D)3-methyloctane

Question 23

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

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

Question 24

The following conversion could be accomplished using a Grignard reaction.

Question 25

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

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

Question 26

The following reaction would be classified as a Simmons-Smith reaction.

Question 27

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

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

Question 28

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

A)(E) 2-iodo-2-butene
B)1-iodo-2-methylpropene
C)methylcyclopropane
D)(E) 2-butene

Question 29

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

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

Question 30

What reactive intermediates are involved in the following reaction?

A)the trichloromethyl anion (Cl₃C:^-) and dichlorocarbene (Cl₂C:)
B)the trichloromethyl cation (Cl₃C⁺)
C)the cyclohexyl carbocation
D)the cyclic chloronium ion derived from cyclohexene

Question 31

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

A)(E) 6,6-dimethyl-1-hexene
B)(E) 5,5-dimethyl-1-heptene
C)(E) 6,6-dimethyl-1-heptene
D)(E) 6,6-dimethyl-2-heptene

Question 32

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

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

Question 33

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

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

Question 34

The reaction of an alkene with dichlorocarbene is stereospecific.

Question 35

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

A)2-iodo-7-methyloctane
B)(E)-7-methyl-1-octene
C)(E)-7-methyl-2-octene
D)(E)-7-methyl-3-octene

Question 36

In a coupling reaction using a Gilman reagent, both of the Gilman reagent alkyl groups are transferred in the reaction

Question 37

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

A)(Z)-6-methyl-2-heptene
B)(E)-4-methyl-2-pentene
C)2-methylheptane
D)3-methylheptane

Question 38

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

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

Question 39

The product of the following reaction would be a cyclopropane.

Question 40

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

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

Question 41

Consider the following reaction to answer the following question(s).
Substance ____ is the nucleophile in the reaction.

A)A
B)B
C)C

Question 42

Consider the following reaction. The name of the product that should be placed in the box is __________________.

Question 43

Consider the following conversion. Use this reacton to answer the following questions.
The first step in this conversion would be reaction with:

A) Mg/ether
B) PCC
C) oxirane

Question 44

In the formation of the ether soluble complex in a Grignard reaction, magnesium acts as a Lewis base and the ether as a Lewis acid.

Question 45

Consider the following reaction to answer the following question(s).
Substance A is formed from the reaction of Mg with ______________.

Question 46

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

Question 47

Name the product of the following reaction.

Question 48

The name of the product of the reaction of 2-chlorobutane with 1.) Li, 2.) CuI, 3.) 1-bromobutane would be _______________________.

Question 49

Consider the reaction below to answer the following question(s).
In this reaction the alkene would be classified as the:

A) electrophile
B) nucleophile
C) Lewis base
D) both b and c

Question 50

Consider the following conversion. Use this reacton to answer the following questions.
The second step in this conversion would be reaction with:

A) Mg/ether
B) PCC
C) oxirane

Question 51

The percent ionic character of a C-Mg bond is less than that of a C-Cu bond.

Question 52

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

Question 53

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

Question 54

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

Question 55

In organometallic bonds, carbon attains a partial negative charge which makes it both basic and nucleophilic.

Question 56

Consider the following reaction to answer the following question(s).
Substance ____ is the electrophile in the reaction.

A)A
B)B
C)C
D)D

Question 57

Consider the reaction below to answer the following question(s).
The reaction intermediate formed by the reaction of KOH with the alkene is called_____________.

Question 58

Consider the following conversion. Use this reacton to answer the following questions.
The first step in this conversion would be reaction with:

A) Mg/ether
B) PCC
C) oxirane

Question 59

Both Grignard reagents and Gilman reagents are synthetically useful because they form new carbon to carbon bonds.

Question 60

Consider the following reaction to answer the following question(s).
Substance A is termed a ___________reagent.

Question 61

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

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 sequence of reactions?

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?