Deck 15: An Introduction to Organometallic Compounds

Question 1

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

Answer 1

only 1 and 2

Question 2

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

Answer 2

oxidative addition

Question 3

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

Answer 3

only 2 and 4

Question 4

Which of the following compounds is the strongest base?

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

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

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

Question 7

Which of the following bonds has the most ionic character?

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

Question 8

Which of the following molecules are deprotonated by ethylmagnesium bromide?

A) phenol, PhOH
B) propyne, CH₃CºCH
C) dimethylamine, (CH₃)₂NH
D) all of these

Question 9

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

A) 0 +1
B) 0 +2
C) 0 -1
D) 0 -2

Question 10

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 11

Which of the following compounds is the strongest base?

A) NaOH
B) NH₃
C) CH₃Li
D) CH₃OH

Question 12

Which of the following bonds has the most ionic character?

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

Question 13

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 14

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

Question 15

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

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

Question 16

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 17

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 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 sequence of reactions?

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 obtained from the following reaction?

Question 23

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

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

Question 24

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 25

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 26

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 27

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

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

Question 28

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

Question 29

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

Question 30

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

Question 31

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

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

Question 32

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 33

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

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 obtained from the following reaction?

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?

Question 38

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 39

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 40

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 41

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

Question 42

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

Question 43

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

Question 44

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

Question 45

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