Question 1

Suggest possible compounds for A and B in the following scheme: CH3CH2I + A → CH3CH2SH + B

Accepted Answer

A)  A is HS- and B is I- 
B)  A is H2S and B is I2 
C)  A is H2S and B is HI 
D)  A is S2- and B is I- 
E)  A is H2S and B is I- 
A)  A is HS- and B is I- 
B)  A is H2S and B is I2 
C)  A is H2S and B is HI 
D)  A is S2- and B is I- 
E)  A is H2S and B is I- A

Question 2

Give the product(s) of the reaction: CH2=CHCH3 + HCl → product(s)

Accepted Answer

A)  CH3CH2CH3 + H2 
B)  CH2ClCHClCH3 + H2 
C)  CH3CHClCH3 
D)  CH2ClCH2CH3 
E)  none of these 
A)  CH3CH2CH3 + H2 
B)  CH2ClCHClCH3 + H2 
C)  CH3CHClCH3 
D)  CH2ClCH2CH3 
E)  none of these C

Question 3

When (CH3)3CBr reacts with CH3ONa in methanol, two products are formed: a major one is an alkene and minor one is an ether. Identify the two products and by what mechanism(s) they are formed?

Accepted Answer

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

Question 4

The formation of isopropanol (rubbing alcohol) through the following hydrolysis is known as what type of general reaction?

Accepted Answer

A)  oxidation 
B)  aromatic substitution 
C)  addition reaction 
D)  elimination 
E)  substitution reaction 
A)  oxidation 
B)  aromatic substitution 
C)  addition reaction 
D)  elimination 
E)  substitution reaction

Question 5

Arrange the following alkenes according to their increasing stability:

Accepted Answer

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

Question 6

Suggest possible compounds for A, B and C in the following scheme:

Accepted Answer

A)  A is Cl2, B is AlCl3 and C is meta chloronitrobenzene 
B)  A is Cl2, B is FeCl3 and C is ortho chloronitrobenzene 
C)  A is Cl2, B is FeBr3 and C is meta chloronitrobenzene 
D)  A is HCl, B is AlCl3 and C is para chloronitrobenzene 
E)  A is Cl2, B is AlBr3 and C is meta chloronitrobenzene 
A)  A is Cl2, B is AlCl3 and C is meta chloronitrobenzene 
B)  A is Cl2, B is FeCl3 and C is ortho chloronitrobenzene 
C)  A is Cl2, B is FeBr3 and C is meta chloronitrobenzene 
D)  A is HCl, B is AlCl3 and C is para chloronitrobenzene 
E)  A is Cl2, B is AlBr3 and C is meta chloronitrobenzene

Question 7

Nucleophiles are electron poor atoms, ions or groups

Accepted Answer

A) True 
 B)False

Question 8

What is the main product of the following reaction?

Accepted Answer

A)  1-bromopropane 
B)  2-bromopropane 
C)  propyl alcohol 
D)  2-bromopropene 
E)  1-bromo-2-methylethane 
A)  1-bromopropane 
B)  2-bromopropane 
C)  propyl alcohol 
D)  2-bromopropene 
E)  1-bromo-2-methylethane

Question 9

What type of polymerization reaction occurred to produce the following polymer?

Accepted Answer

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

Question 10

A hydrocarbon has a molecular weight 56 g/mol and contains 85.7% carbon. It easily adds one mol of HBr to produce a chiral alkyl bromide. Which of the following structures could be our hydrocarbon?

Accepted Answer

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

Question 11

Which of the following could be added across carbon-carbon multiple bonds? 
I. H2SO4
II. H2
III. H2O
IV. NO2
V. HBr

Accepted Answer

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

Question 12

Hyperconjugation is best described as:

Accepted Answer

A)  an interaction between the orbitals on a substrate and orbitals on a nucleophile 
B)  an interaction between σ bonds and π network 
C)  a resonance structure with separated charges 
D)  an interaction between two π networks 
E)  an electrostatic interaction between an electrophile and a nucleophile 
A)  an interaction between the orbitals on a substrate and orbitals on a nucleophile 
B)  an interaction between σ bonds and π network 
C)  a resonance structure with separated charges 
D)  an interaction between two π networks 
E)  an electrostatic interaction between an electrophile and a nucleophile

Question 13

Reactions between alkanes and HX compounds are typical examples of addition reactions.

Accepted Answer

A) True 
 B)False

Question 14

What is(are) the main product(s) of the following chlorination reaction?

Accepted Answer

A)  3-chloro-5-cyanobenzaldehyde 
B)  2, 6-dichloro-3-cyanobenzaldehyde 
C)  2-chloro-3-cyanobenzaldehyde 
D)  2-chloro-3-cyanobenzaldehyde and 2-chloro-5-cyanobenzaldehyde 
E)  B and D 
A)  3-chloro-5-cyanobenzaldehyde 
B)  2, 6-dichloro-3-cyanobenzaldehyde 
C)  2-chloro-3-cyanobenzaldehyde 
D)  2-chloro-3-cyanobenzaldehyde and 2-chloro-5-cyanobenzaldehyde 
E)  B and D

Question 15

Oxidation of the following alcohol via the conditions below yields spearmint oil. What new functional group is formed in the reaction to yield spearmint?

Accepted Answer

A)  aldehyde 
B)  carboxylic acid 
C)  ketone 
D)  amine 
E)  ester 
A)  aldehyde 
B)  carboxylic acid 
C)  ketone 
D)  amine 
E)  ester

Question 16

Which of the following compounds could be used as catalysts in halogenation of benzene?
 I. AlCl3
II. NaCl
III. FeBr3
IV. MgCl2
V. PbCl2

Accepted Answer

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

Question 17

Markovnikof's rule predicts that when HBr is added to an unsymmetrical alkene or alkyne, the H atom will add to which carbon atom?

Accepted Answer

A)  the carbon with the fewest attached hydrogens 
B)  the carbon with the Br 
C)  the carbon with the most attached hydrogens 
D)  the carbon next to the double or triple bond 
E)  HBr does not react with unsymmetrical alkenes or alkynes. 
A)  the carbon with the fewest attached hydrogens 
B)  the carbon with the Br 
C)  the carbon with the most attached hydrogens 
D)  the carbon next to the double or triple bond 
E)  HBr does not react with unsymmetrical alkenes or alkynes.

Question 18

Arrange the following carbocations in order of decreasing stability:

Accepted Answer

A)  A > B > C. 
B)  C > B > A 
C)  A > B > C 
D)  C > A > B. 
E)  B > A > C. 
A)  A > B > C. 
B)  C > B > A 
C)  A > B > C 
D)  C > A > B. 
E)  B > A > C.

Question 19

Predict the major product for the reaction: CH3C≡CH + 2HBr →

Accepted Answer

A)  CH3CBr2CH3 
B)  CH3CH2CHBr2 
C)  CH3CHBrCH2Br 
D)  CH2=CBrCH2Br 
E)  no reaction 
A)  CH3CBr2CH3 
B)  CH3CH2CHBr2 
C)  CH3CHBrCH2Br 
D)  CH2=CBrCH2Br 
E)  no reaction

Question 20

The initiation step in chain reaction for alkene substitution produces:

Accepted Answer

A)  free halogen radicals 
B)  free alkyl radicals 
C)  both free halogen and alkyl radicals 
D)  free halonium ions 
E)  free halide ions 
A)  free halogen radicals 
B)  free alkyl radicals 
C)  both free halogen and alkyl radicals 
D)  free halonium ions 
E)  free halide ions

Exam 27: Reactions of Organic Compounds

Suggest possible compounds for A and B in the following scheme: CH3CH2I + A → CH3CH2SH + B

Give the product(s) of the reaction: CH2=CHCH3 + HCl → product(s)

When (CH3)3CBr reacts with CH3ONa in methanol, two products are formed: a major one is an alkene and minor one is an ether. Identify the two products and by what mechanism(s) they are formed?

The formation of isopropanol (rubbing alcohol) through the following hydrolysis is known as what type of general reaction?

Arrange the following alkenes according to their increasing stability:

Suggest possible compounds for A, B and C in the following scheme:

Nucleophiles are electron poor atoms, ions or groups

What is the main product of the following reaction?

What type of polymerization reaction occurred to produce the following polymer?

A hydrocarbon has a molecular weight 56 g/mol and contains 85.7% carbon. It easily adds one mol of HBr to produce a chiral alkyl bromide. Which of the following structures could be our hydrocarbon?

Which of the following could be added across carbon-carbon multiple bonds? I. H2SO4 II. H2 III. H2O IV. NO2 V. HBr

Hyperconjugation is best described as:

Reactions between alkanes and HX compounds are typical examples of addition reactions.

What is(are) the main product(s) of the following chlorination reaction?

Oxidation of the following alcohol via the conditions below yields spearmint oil. What new functional group is formed in the reaction to yield spearmint?

Which of the following compounds could be used as catalysts in halogenation of benzene? I. AlCl3 II. NaCl III. FeBr3 IV. MgCl2 V. PbCl2

Markovnikof's rule predicts that when HBr is added to an unsymmetrical alkene or alkyne, the H atom will add to which carbon atom?

Arrange the following carbocations in order of decreasing stability:

Predict the major product for the reaction: CH3C≡CH + 2HBr →

The initiation step in chain reaction for alkene substitution produces:

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

Suggest possible compounds for A and B in the following scheme: CH₃CH₂I + A → CH₃CH₂SH + B

Give the product(s) of the reaction: CH₂=CHCH₃ + HCl → product(s)

When (CH₃)₃CBr reacts with CH₃ONa in methanol, two products are formed: a major one is an alkene and minor one is an ether. Identify the two products and by what mechanism(s) they are formed?

Which of the following could be added across carbon-carbon multiple bonds? I. H₂SO₄ II. H₂ III. H₂O IV. NO₂ V. HBr

Which of the following compounds could be used as catalysts in halogenation of benzene? I. AlCl₃ II. NaCl III. FeBr₃ IV. MgCl₂ V. PbCl₂

Predict the major product for the reaction: CH₃C≡CH + 2HBr →