Question 1

What is arenium ion?

Accepted Answer

A)  a carbocation formed after the electrophilic attack on the benzene ring 
B)  a carbocation formed from a molecule containing an arene ring 
C)  a carbocation formed during the elimination reaction from an aromatic molecule 
D)  a carboanion formed from deprotonation of benzene ring 
E)  a carboanion formed after nucleophilic attack on the benzene ring 
A)  a carbocation formed after the electrophilic attack on the benzene ring 
B)  a carbocation formed from a molecule containing an arene ring 
C)  a carbocation formed during the elimination reaction from an aromatic molecule 
D)  a carboanion formed from deprotonation of benzene ring 
E)  a carboanion formed after nucleophilic attack on the benzene ring

Question 2

Which are the most probable reactions and mechanisms in which tertiary haloalkanes participate? 
I Substitution, SN1
II. Substitution SN2
III. Elimination E1
IV. Elimination E2
V. Addition

Accepted Answer

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

Question 3

Identify the product for the following reaction:

Accepted Answer

A)  3-methyl-1-pentene 
B)  3-methyl-2-pentene 
C)  3-methyl-1-pentane 
D)  3-methyl-1-tert-butylpentante 
E)  3-methylpentane 
A)  3-methyl-1-pentene 
B)  3-methyl-2-pentene 
C)  3-methyl-1-pentane 
D)  3-methyl-1-tert-butylpentante 
E)  3-methylpentane

Question 4

Arrange the following radicals in the order of increasing stability:

Accepted Answer

A)  B < A < C 
B)  C < A < B 
C)  A < B < C 
D)  C < B < A 
E)  B < C < A 
A)  B < A < C 
B)  C < A < B 
C)  A < B < C 
D)  C < B < A 
E)  B < C < A

Question 5

What is the major product in the following transformation?

Accepted Answer

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

Question 6

Which type of polymerization and which monomer(s) would you use to prepare poly(1,4-phenylenediformamide) with the following structure?

Accepted Answer

A) 
 
With chain reaction polymerization 
B) 
 
With condensation polymerization 
C) 
 
With chain reaction polymerization 
D) 
 
With step-reaction polymerization 
E) 
 
With chain reaction polymerization 
A) 
 
With chain reaction polymerization 
B) 
 
With condensation polymerization 
C) 
 
With chain reaction polymerization 
D) 
 
With step-reaction polymerization 
E) 
 
With chain reaction polymerization

Question 7

Which of the following groups would be ortho, para directors in electrophilic aromatic substitution? 
I. -CN
II. -SO3H
III. -NH2
IV. -OH
V. -Br

Accepted Answer

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

Question 8

Which of the following is an unsymmetrical reagent?

Accepted Answer

A)  Cl2 
B)  H2O 
C)  H2O and HCl 
D)  HCl 
E)  I2 
A)  Cl2 
B)  H2O 
C)  H2O and HCl 
D)  HCl 
E)  I2

Question 9

What is "retrosynthesis"?

Accepted Answer

A)  a chemical analysis followed by chemical synthesis 
B)  a chemical synthesis followed by chemical analysis 
C)  a synthetic procedure designed to check old synthetic procedure 
D)  a synthetic strategy that works from the desired compound towards starting materials 
E)  a synthetic strategy that works from the starting materials towards desired product 
A)  a chemical analysis followed by chemical synthesis 
B)  a chemical synthesis followed by chemical analysis 
C)  a synthetic procedure designed to check old synthetic procedure 
D)  a synthetic strategy that works from the desired compound towards starting materials 
E)  a synthetic strategy that works from the starting materials towards desired product

Question 10

SN2 reactions are nucleophilic substitution reactions for which the rate determining step is bimolecular.

Accepted Answer

A) True 
 B)False

Question 11

Which of the following mechanistic steps do you expect in bromination of benzene with Br2 and FeBr3 as a catalyst?
 I. Formation of Br+[FeBr4]-
II. Attack of [FeBr4]- on benzene ring
III. Formation of arenium ion
IV. Deprotonation of arenium ion
V. Nucleophilic attack of Br+

Accepted Answer

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

Question 12

What is the major product in the reaction between 2-bromo-3-methylbutane and KOtBu in ethanol?

Accepted Answer

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

Question 13

What is the rate law for the SN1 reactions (S is substrate and N is nucleophile) ?

Accepted Answer

A)  rate = k[S][N] 
B)  rate = k[S] 
C)  rate = k[N} 
D)  rate = k[S]2 
E)  rate = k[S][N}2 
A)  rate = k[S][N] 
B)  rate = k[S] 
C)  rate = k[N} 
D)  rate = k[S]2 
E)  rate = k[S][N}2

Question 14

Which of the following steps can be found in E1 reaction mechanism? 
I. Formation of a carbocation
II. Attack of the base and removal of a proton from carbocation
III. Attack of a nucleophile
IV. Formation of a carboanion

Accepted Answer

A)  I and II 
B)  only II 
C)  I and III 
D)  III and IV 
E)  only III 
A)  I and II 
B)  only II 
C)  I and III 
D)  III and IV 
E)  only III

Question 15

Identify the product(s) and mechanism for the following reaction:

Accepted Answer

A) 
 
SN1 mechanism 
B) 
 
SN2 mechanism 
C) 
 
SN1 mechanism 
D) 
 
SN2 mechanism 
E) 
 
SN2 mechanism 
A) 
 
SN1 mechanism 
B) 
 
SN2 mechanism 
C) 
 
SN1 mechanism 
D) 
 
SN2 mechanism 
E) 
 
SN2 mechanism

Question 16

Lindlar's catalyst is used when ________.

Accepted Answer

A)  we want to reduce alkynes to alkanes 
B)  we want to speed up HX addition reactions 
C)  we have to promote elimination reactions over substitution reactions 
D)  we need to activate Pd hydrogenation catalyst 
E)  we want to reduce alkynes to Z alkenes 
A)  we want to reduce alkynes to alkanes 
B)  we want to speed up HX addition reactions 
C)  we have to promote elimination reactions over substitution reactions 
D)  we need to activate Pd hydrogenation catalyst 
E)  we want to reduce alkynes to Z alkenes

Question 17

Arrange the following in the order of decreasing nucleophilicity: H2N-, HO-, HCOO-, CH3O-

Accepted Answer

A)  H2N- > HO- > HCOO- > CH3O- 
B)  H2N- > CH3O- > HO- > HCOO- 
C)  H2N- > HO- > CH3O- > HCOO- 
D)  HO- > H2N- > CH3O- > HCOO- 
E)  CH3O- > HO- > H2N- > HCOO- 
A)  H2N- > HO- > HCOO- > CH3O- 
B)  H2N- > CH3O- > HO- > HCOO- 
C)  H2N- > HO- > CH3O- > HCOO- 
D)  HO- > H2N- > CH3O- > HCOO- 
E)  CH3O- > HO- > H2N- > HCOO-

Question 18

Predict the major product for the reaction: 2-methyl-2-butene + HBr →

Accepted Answer

A)  (CH3)2CBrCH2CH3 
B)  (CH3)2CBrCH=CH2 
C)  (CH3)2CHCHBrCH3 
D)  CH2=C(CH3)CH2CH3 
E)  no reaction 
A)  (CH3)2CBrCH2CH3 
B)  (CH3)2CBrCH=CH2 
C)  (CH3)2CHCHBrCH3 
D)  CH2=C(CH3)CH2CH3 
E)  no reaction

Question 19

Chain reaction polymerization is typical for:

Accepted Answer

A)  monomers with carbon-carbon double bonds 
B)  monomers with carbon oxygen double bonds 
C)  monomers containing aromatic rings 
D)  monomeric alkanes 
E)  monomeric alcohols 
A)  monomers with carbon-carbon double bonds 
B)  monomers with carbon oxygen double bonds 
C)  monomers containing aromatic rings 
D)  monomeric alkanes 
E)  monomeric alcohols

Question 20

The step reaction polymerizations are fast polymerization reactions

Accepted Answer

A) True 
 B)False

Exam 27: Reactions of Organic Compounds

What is arenium ion?

Which are the most probable reactions and mechanisms in which tertiary haloalkanes participate? I Substitution, SN1 II. Substitution SN2 III. Elimination E1 IV. Elimination E2 V. Addition

Identify the product for the following reaction:

Arrange the following radicals in the order of increasing stability:

What is the major product in the following transformation?

Which type of polymerization and which monomer(s) would you use to prepare poly(1,4-phenylenediformamide) with the following structure?

Which of the following groups would be ortho, para directors in electrophilic aromatic substitution? I. -CN II. -SO3H III. -NH2 IV. -OH V. -Br

Which of the following is an unsymmetrical reagent?

What is "retrosynthesis"?

SN2 reactions are nucleophilic substitution reactions for which the rate determining step is bimolecular.

Which of the following mechanistic steps do you expect in bromination of benzene with Br2 and FeBr3 as a catalyst? I. Formation of Br+[FeBr4]- II. Attack of [FeBr4]- on benzene ring III. Formation of arenium ion IV. Deprotonation of arenium ion V. Nucleophilic attack of Br+

What is the major product in the reaction between 2-bromo-3-methylbutane and KOtBu in ethanol?

What is the rate law for the SN1 reactions (S is substrate and N is nucleophile) ?

Which of the following steps can be found in E1 reaction mechanism? I. Formation of a carbocation II. Attack of the base and removal of a proton from carbocation III. Attack of a nucleophile IV. Formation of a carboanion

Identify the product(s) and mechanism for the following reaction:

Lindlar's catalyst is used when ________.

Arrange the following in the order of decreasing nucleophilicity: H2N-, HO-, HCOO-, CH3O-

Predict the major product for the reaction: 2-methyl-2-butene + HBr →

Chain reaction polymerization is typical for:

The step reaction polymerizations are fast polymerization reactions

Matter - Its Properties and Measurement

Atoms and the Atomic Theory

Chemical Compounds

Chemical Reactions

Introduction to Reactions in Aqueous Solutions

Gases

Thermochemistry

Electrons in Atoms

The Periodic Table and Some Atomic Properties

Chemical Bonding I: Basic Concepts

Chemical Bonding II: Additional Aspects

Intermolecular Forces: Liquids and Solids

Solutions and Their Physical Properties

Chemical Kinetics

Principles of Chemical Equilibrium

Acids and Bases

Additional Aspects of Acid-Base Equilibria

Solubility and Complex-Ion Equilibria

Spontaneous Change: Entropy and Free Energy

Electrochemistry

Main Group Elements I: Groups 1, 2, 13, and 14

Main Group Elements II: Groups 18, 17, 16, 15, and Hydrogen

The Transition Elements

Complex Ions and Coordination Compounds

Nuclear Chemistry 1-41

Structures of Organic Compounds

Chemistry of the Living State

Filters

Which of the following groups would be ortho, para directors in electrophilic aromatic substitution? I. -CN II. -SO₃H III. -NH₂ IV. -OH V. -Br

SN₂ reactions are nucleophilic substitution reactions for which the rate determining step is bimolecular.

Which of the following mechanistic steps do you expect in bromination of benzene with Br₂ and FeBr₃ as a catalyst? I. Formation of Br+[FeBr4]- II. Attack of [FeBr4]- on benzene ring III. Formation of arenium ion IV. Deprotonation of arenium ion V. Nucleophilic attack of Br+

Arrange the following in the order of decreasing nucleophilicity: H₂N^-, HO^-, HCOO^-, CH₃O^-