Question 1

Rank the following compounds in order of increasing reactivity towards chlorination with Cl2/AlCl3 (slowest reacting to fastest).

Accepted Answer

A)  3 < 4 < 2 < 1 < 5 
B)  2 < 4 < 1 < 3 < 5 
C)  4 < 2 < 1 < 3 < 5 
D)  2 < 4 < 5 < 1 < 3 
E)  2 < 4 < 1 < 5 < 3 
A)  3 < 4 < 2 < 1 < 5 
B)  2 < 4 < 1 < 3 < 5 
C)  4 < 2 < 1 < 3 < 5 
D)  2 < 4 < 5 < 1 < 3 
E)  2 < 4 < 1 < 5 < 3

Question 2

Provide a series of synthetic steps by which p-nitrophenol can be prepared from benzene.

Accepted Answer

1) Cl₂, AlC

Question 3

Provide a series of synthetic steps by which the compound below can be prepared from benzene.

Accepted Answer

1) (CH₃)₂CHC

Question 4

In electrophilic aromatic substitution reactions, a phenyl substituent on the aromatic ring is ________.

Accepted Answer

A)  a deactivator and a m-director 
B)  a deactivator and an o,p-director 
C)  an activator and a m-director 
D)  an activator and an o,p-director 
E)  none of the above 
A)  a deactivator and a m-director 
B)  a deactivator and an o,p-director 
C)  an activator and a m-director 
D)  an activator and an o,p-director 
E)  none of the above

Question 5

Explain why this reaction won't take place.

Accepted Answer

The intermediate in this react

Question 6

List two of the three limitations usually associated with the Friedel-Crafts alkylation reaction.

Accepted Answer

1) Reaction fails when strongl

Question 7

Under what reaction conditions does the electrophilic chlorination of aromatic compounds usually occur?

Accepted Answer

A)  Cl2, AlCl3 
B)  Cl2, H2O 
C)  Cl2, CCl4 
D)  NaCl, H2O 
E)  NaCl, CH3OH 
A)  Cl2, AlCl3 
B)  Cl2, H2O 
C)  Cl2, CCl4 
D)  NaCl, H2O 
E)  NaCl, CH3OH

Question 8

Which of the following is an incorrect statement about the bromination of benzene by Br2 and FeBr3?

Accepted Answer

A)  FeBr3 functions to increase the electrophilicity of Br2. 
B)  Formation of the sigma complex is the rate-determining step of the mechanism. 
C)  The carbanionic intermediate is resonance stabilized. 
D)  There is one carbon-containing intermediates in the mechanism. 
E)  The final step of the mechanism is loss of H+. 
A)  FeBr3 functions to increase the electrophilicity of Br2. 
B)  Formation of the sigma complex is the rate-determining step of the mechanism. 
C)  The carbanionic intermediate is resonance stabilized. 
D)  There is one carbon-containing intermediates in the mechanism. 
E)  The final step of the mechanism is loss of H+.

Question 9

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

Accepted Answer

The answer of Provide the structure of the major organic...

Question 10

Provide the structures of the major organic products in the following reaction.

Accepted Answer

The answer of Provide the structures of the major organic...

Question 11

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 12

Which series of reagents would be required to perform the following synthesis?

Accepted Answer

A)  1. ClCH2CH2CH3, AlCl3 2. FeBr3, Br2 
B)  1. ClCOCH2CH3, AlCl3 2. FeBr3, Br2 
C)  1. ClCOCH2CH3, AlCl3 2. FeBr3, Br2 3. Zn(Hg), HCl 
D)  1. ClCOCH2CH3, AlCl3 2. Zn(Hg), HCl 3. FeBr3, Br2 
A)  1. ClCH2CH2CH3, AlCl3 2. FeBr3, Br2 
B)  1. ClCOCH2CH3, AlCl3 2. FeBr3, Br2 
C)  1. ClCOCH2CH3, AlCl3 2. FeBr3, Br2 3. Zn(Hg), HCl 
D)  1. ClCOCH2CH3, AlCl3 2. Zn(Hg), HCl 3. FeBr3, Br2

Question 13

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 14

Which of the following compounds will react most rapidly when treated with CH3CH2Cl and AlCl3?

Accepted Answer

A)  benzene 
B)  chlorobenzene 
C)  nitrobenzene 
D)  anisole 
E)  toluene 
A)  benzene 
B)  chlorobenzene 
C)  nitrobenzene 
D)  anisole 
E)  toluene

Question 15

Provide the resonance form of the intermediate in the reaction shown below that highlights the directing effect of the nitro group.

Accepted Answer

The answer of Provide the resonance form of the intermediate...

Question 16

In electrophilic aromatic substitution reactions the nitro group is ________.

Accepted Answer

A)  a m-director since it destabilizes the meta sigma complex more than the ortho, para 
B)  a m-director since it destabilizes the meta sigma complex less than the ortho, para 
C)  an o,p-director since it stabilizes the ortho, para sigma complex more than the meta 
D)  an o,p-director since it stabilizes the ortho, para sigma complex less than the meta 
E)  none of the above 
A)  a m-director since it destabilizes the meta sigma complex more than the ortho, para 
B)  a m-director since it destabilizes the meta sigma complex less than the ortho, para 
C)  an o,p-director since it stabilizes the ortho, para sigma complex more than the meta 
D)  an o,p-director since it stabilizes the ortho, para sigma complex less than the meta 
E)  none of the above

Question 17

Provide a series of synthetic steps by which 4-t-butylbenzoic acid can be prepared from toluene.

Accepted Answer

1) (CH₃)₃CCl

Question 18

Predict the product of the following intramolecular Heck reaction (Synthesis, 2002, 28, 87).

Accepted Answer

The answer of Predict the product of the following intramolecular...

Question 19

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 20

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Exam 17: Reactions of Aromatic Compounds

Rank the following compounds in order of increasing reactivity towards chlorination with Cl2/AlCl3 (slowest reacting to fastest).

Provide a series of synthetic steps by which p-nitrophenol can be prepared from benzene.

Provide a series of synthetic steps by which the compound below can be prepared from benzene.

In electrophilic aromatic substitution reactions, a phenyl substituent on the aromatic ring is ________.

Explain why this reaction won't take place.

List two of the three limitations usually associated with the Friedel-Crafts alkylation reaction.

Under what reaction conditions does the electrophilic chlorination of aromatic compounds usually occur?

Which of the following is an incorrect statement about the bromination of benzene by Br2 and FeBr3?

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

Provide the structures of the major organic products in the following reaction.

Provide the major organic product of the following reaction.

Which series of reagents would be required to perform the following synthesis?

Provide the major organic product of the following reaction.

Which of the following compounds will react most rapidly when treated with CH3CH2Cl and AlCl3?

Provide the resonance form of the intermediate in the reaction shown below that highlights the directing effect of the nitro group.

In electrophilic aromatic substitution reactions the nitro group is ________.

Provide a series of synthetic steps by which 4-t-butylbenzoic acid can be prepared from toluene.

Predict the product of the following intramolecular Heck reaction (Synthesis, 2002, 28, 87).

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Rank the following compounds in order of increasing reactivity towards chlorination with Cl₂/AlCl₃ (slowest reacting to fastest).

Which of the following is an incorrect statement about the bromination of benzene by Br₂ and FeBr₃?

Which of the following compounds will react most rapidly when treated with CH₃CH₂Cl and AlCl₃?