Question 1

Which combination of reagents would you use to prepare chlorobenzene (C6H5Cl)from benzene (C6H6)?

Accepted Answer

A) Cl2 and FeBr3 
B) HCl and H2SO4 
C) Cl2 and FeCl3 
D) HClO and FeCl3 
E) HCl and HNO3 
A) Cl2 and FeBr3 
B) HCl and H2SO4 
C) Cl2 and FeCl3 
D) HClO and FeCl3 
E) HCl and HNO3

Question 2

Which of the following statements is TRUE?

Accepted Answer

A) Elimination reactions proceed via either an E1 mechanism,which is a one-step mechanism,or an E2 mechanism,which is a two-step mechanism. 
B) The E1 mechanism is somewhat similar to the SN1 mechanism: they both start with a dissociation step in which a carbocation is formed. 
C) Primary alcohols and alkylhalides are very likely to react via an E1 mechanism because they produce stable carbocations. 
D) The strength of base used in elimination reactions is not important for the E2 mechanism because the base contributes only to the second step of the E2 mechanism. 
E) E2 elimination reactions can occur at primary carbon centres but not at secondary and tertiary carbon atoms. 
A) Elimination reactions proceed via either an E1 mechanism,which is a one-step mechanism,or an E2 mechanism,which is a two-step mechanism. 
B) The E1 mechanism is somewhat similar to the SN1 mechanism: they both start with a dissociation step in which a carbocation is formed. 
C) Primary alcohols and alkylhalides are very likely to react via an E1 mechanism because they produce stable carbocations. 
D) The strength of base used in elimination reactions is not important for the E2 mechanism because the base contributes only to the second step of the E2 mechanism. 
E) E2 elimination reactions can occur at primary carbon centres but not at secondary and tertiary carbon atoms.

Question 3

Write a balanced chemical reaction to represent the combustion of 2,2-dimethylpropane.

Accepted Answer

A) C5H12 + 8O2 → 5CO2 + 6H2O 
B) C3H8 + 5O2 → 3CO2 + 4H2O 
C) C5H12 + H2 → CH4 + 2C2H6 
D) C3H8 + H2 → CH4 + C2H6 
E) 2C3H8 + O2 → 3CH4 + 2H2O 
A) C5H12 + 8O2 → 5CO2 + 6H2O 
B) C3H8 + 5O2 → 3CO2 + 4H2O 
C) C5H12 + H2 → CH4 + 2C2H6 
D) C3H8 + H2 → CH4 + C2H6 
E) 2C3H8 + O2 → 3CH4 + 2H2O

Question 4

Which of the following statements is TRUE?

Accepted Answer

A) In nucleophilic substitution reactions at a saturated carbon atom,a carbon with a positive charge behaves as a nucleophile. 
B) Nucleophilic substitution reactions at a saturated carbon atom can follow one of three mechanisms: SN1,SN2,and SN3. 
C) A carbon atom with a partial positive charge can react with a nucleophile,a molecule,or ion that has a lone pair of electrons. 
D) Alkanes are an example of saturated organic compounds that easily participate in nucleophilic substitution reactions at a saturated carbon atom. 
E) In nucleophilic substitution reactions at a saturated carbon atom,the replaced group is called an electrophile. 
A) In nucleophilic substitution reactions at a saturated carbon atom,a carbon with a positive charge behaves as a nucleophile. 
B) Nucleophilic substitution reactions at a saturated carbon atom can follow one of three mechanisms: SN1,SN2,and SN3. 
C) A carbon atom with a partial positive charge can react with a nucleophile,a molecule,or ion that has a lone pair of electrons. 
D) Alkanes are an example of saturated organic compounds that easily participate in nucleophilic substitution reactions at a saturated carbon atom. 
E) In nucleophilic substitution reactions at a saturated carbon atom,the replaced group is called an electrophile.

Question 5

Which of the following statements is TRUE?

Accepted Answer

A) During the electrophilic aromatic substitutions,the resonance stabilized carbocation reacts with a base to give the addition product. 
B) Aromatic compounds are very reactive because they contain more than one C=C double bond in their structure. 
C) The rate-determining (slow)step of electrophilic aromatic substitutions is the deprotonation of the carbocation intermediate. 
D) Unlike alkenes,aromatic compounds almost always prefer electrophilic substitution over electrophilic addition. 
E) During the electrophilic aromatic substitution a Bronsted or Lewis acid is required to generate the nucleophile from an aromatic substrate. 
A) During the electrophilic aromatic substitutions,the resonance stabilized carbocation reacts with a base to give the addition product. 
B) Aromatic compounds are very reactive because they contain more than one C=C double bond in their structure. 
C) The rate-determining (slow)step of electrophilic aromatic substitutions is the deprotonation of the carbocation intermediate. 
D) Unlike alkenes,aromatic compounds almost always prefer electrophilic substitution over electrophilic addition. 
E) During the electrophilic aromatic substitution a Bronsted or Lewis acid is required to generate the nucleophile from an aromatic substrate.

Question 6

What are polymers?

Accepted Answer

A) Polymers are long,chain-like molecules composed of small,repeating units called monomers. 
B) Polymers are long,chain-like molecules composed of small,repeating units called copolymers. 
C) Polymers are long,chain-like molecules without fixed composition or structure,commonly of low molecular weight. 
D) Polymers are long,chain-like molecules formed when smaller units,monomers,crystalize together from solution. 
E) Polymers are long,chain-like molecules composed of small,repeating units called oligomers. 
A) Polymers are long,chain-like molecules composed of small,repeating units called monomers. 
B) Polymers are long,chain-like molecules composed of small,repeating units called copolymers. 
C) Polymers are long,chain-like molecules without fixed composition or structure,commonly of low molecular weight. 
D) Polymers are long,chain-like molecules formed when smaller units,monomers,crystalize together from solution. 
E) Polymers are long,chain-like molecules composed of small,repeating units called oligomers.

Question 7

Complete and balance the following addition reaction: 
CH3C ≡ CCH3 + 2Cl2 → ?

Accepted Answer

A) CH3C ≡ CCH3 + 2Cl2 → CH3CCl2CCl2CH3 
B) CH3C ≡ CCH3 + 3Cl2 → 2CH3CCl3 
C) CH3C ≡ CCH3 + 2Cl2 → 4CH3Cl 
D) CH3C ≡ CCH3 + 4Cl2 → 4CH2Cl2 
E) CH3C ≡CCH3 + Cl2 → CH3CHClCHClCH3 
A) CH3C ≡ CCH3 + 2Cl2 → CH3CCl2CCl2CH3 
B) CH3C ≡ CCH3 + 3Cl2 → 2CH3CCl3 
C) CH3C ≡ CCH3 + 2Cl2 → 4CH3Cl 
D) CH3C ≡ CCH3 + 4Cl2 → 4CH2Cl2 
E) CH3C ≡CCH3 + Cl2 → CH3CHClCHClCH3

Question 8

What is the product for the dehydration of CH3CH2CH2OH?

Accepted Answer

A) CH3CH2CH2OCH2CH2CH3 
B) CH3CH=CH2 
C) CH3CH=CHCH3 
D) CH3CH2CH=CH2 
E) CH2=C=CH2 
A) CH3CH2CH2OCH2CH2CH3 
B) CH3CH=CH2 
C) CH3CH=CHCH3 
D) CH3CH2CH=CH2 
E) CH2=C=CH2

Question 9

Predict the correct mechanism and product for the following reaction:

Accepted Answer

A) SN1 mechanism,the product is
  
B) SN2 mechanism,the product is
  
C) SN2 mechanism,the product is
  
D) SN1 mechanism,the product is
  
E) E1 mechanism,the product is
  
A) SN1 mechanism,the product is
  
B) SN2 mechanism,the product is
  
C) SN2 mechanism,the product is
  
D) SN1 mechanism,the product is
  
E) E1 mechanism,the product is

Question 10

Which of the following statements is TRUE?

Accepted Answer

A) Dehydration is an example of a 1,2-elimination reaction in which an alcohol loses one water molecule,forming an alkene. 
B) Dehydrohalogenation is an example of a 1,2 elimination reaction in which an organic molecule loses one water molecule and a halogen atom to produce an alkyne. 
C) There is only one possible mechanistic pathway for an elimination reaction,called the E1 mechanism. 
D) 1,2-elimination reactions are frequently in competition with addition reactions. 
E) Dehydration and dehydrohalogenation are two distinct steps in every 1,2-elimination reaction. 
A) Dehydration is an example of a 1,2-elimination reaction in which an alcohol loses one water molecule,forming an alkene. 
B) Dehydrohalogenation is an example of a 1,2 elimination reaction in which an organic molecule loses one water molecule and a halogen atom to produce an alkyne. 
C) There is only one possible mechanistic pathway for an elimination reaction,called the E1 mechanism. 
D) 1,2-elimination reactions are frequently in competition with addition reactions. 
E) Dehydration and dehydrohalogenation are two distinct steps in every 1,2-elimination reaction.

Question 11

Which of the following five substrates is the most likely to be the substrate in an SN2 reaction?

Accepted Answer

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

Question 12

Determine the products of the following reaction:

Accepted Answer

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

Question 13

What are addition polymers?

Accepted Answer

A) Addition polymers are formed from monomers that bond together and eliminate a small molecule,usually water. 
B) Addition polymers are polymers formed when monomers add together without formation of covalent bonds. 
C) Addition polymers are formed when small molecules (such as water and HX)add across unsaturated C-C bonds in the polymeric chain. 
D) Addition polymers are formed from monomers that link together without the elimination of a small molecule. 
E) Addition polymers are polymers that grow by adding small monomers to the existing polymer chain with elimination of a water molecule for each new bond formed. 
A) Addition polymers are formed from monomers that bond together and eliminate a small molecule,usually water. 
B) Addition polymers are polymers formed when monomers add together without formation of covalent bonds. 
C) Addition polymers are formed when small molecules (such as water and HX)add across unsaturated C-C bonds in the polymeric chain. 
D) Addition polymers are formed from monomers that link together without the elimination of a small molecule. 
E) Addition polymers are polymers that grow by adding small monomers to the existing polymer chain with elimination of a water molecule for each new bond formed.

Question 14

Why doesn't benzene typically undergo addition reactions like the alkenes do?

Accepted Answer

Benzene's pi electrons are del

Question 15

Give the organic product of the following reaction.   $+ \mathrm { CH } _ { 3 } \mathrm { OH } \stackrel { \mathrm { H } _ { 2 } \mathrm { SO } _ { 4 } } { \longrightarrow }$

Accepted Answer

The answer of Give the organic product of the following...

Question 16

Draw a clear mechanism for E1 elimination reactions.Make sure to indicate each step of the mechanism (if there is more than one)as well as to use arrows to show the electron flow.

Accepted Answer

E1 elimination reactions involve a two-s

Question 17

Which of the following statements is TRUE?

Accepted Answer

A) Elimination reactions take place with the retention of the absolute configuration. 
B) The most common substrates in elimination reactions are ketones and amines. 
C) A dehydration reaction produces an alkane and one equivalent of water. 
D) The major product in an elimination reaction is the less substituted alkene. 
E) A dehydrohalogenation reaction requires the presence of a strong base and heat. 
A) Elimination reactions take place with the retention of the absolute configuration. 
B) The most common substrates in elimination reactions are ketones and amines. 
C) A dehydration reaction produces an alkane and one equivalent of water. 
D) The major product in an elimination reaction is the less substituted alkene. 
E) A dehydrohalogenation reaction requires the presence of a strong base and heat.

Question 18

Which is the strongest organic acid?

Accepted Answer

A) F3CCOOH 
B) F2HCCOOH 
C) H3CCOOH 
D) ClH2CCOOH 
E) FH2CCOOH 
A) F3CCOOH 
B) F2HCCOOH 
C) H3CCOOH 
D) ClH2CCOOH 
E) FH2CCOOH

Question 19

Which of the following statements is TRUE?

Accepted Answer

A) The nucleophile strongly influences both SN1 and SN2 reactions,while the nature of the nucleophile and the substrate structure are only important in SN2 reactions. 
B) The structure of the substrate is the only important factor for SN1 reactions,while the nucleophile,leaving group,and the structure of the substrate are all important for SN2 reactions. 
C) For SN2 reactions the only important factor to consider is the leaving group; for SN1 reactions the structure of the substrate and the nature of the nucleophile are the most important factors. 
D) The nucleophile and leaving group are both important in SN2 reactions,while for the SN1 reactions the leaving group and the structure of the substrate are very significant. 
E) The nucleophile is not important for SN2 reactions,but the structure of the substrate is very important; for SN1 reactions the opposite is true. 
A) The nucleophile strongly influences both SN1 and SN2 reactions,while the nature of the nucleophile and the substrate structure are only important in SN2 reactions. 
B) The structure of the substrate is the only important factor for SN1 reactions,while the nucleophile,leaving group,and the structure of the substrate are all important for SN2 reactions. 
C) For SN2 reactions the only important factor to consider is the leaving group; for SN1 reactions the structure of the substrate and the nature of the nucleophile are the most important factors. 
D) The nucleophile and leaving group are both important in SN2 reactions,while for the SN1 reactions the leaving group and the structure of the substrate are very significant. 
E) The nucleophile is not important for SN2 reactions,but the structure of the substrate is very important; for SN1 reactions the opposite is true.

Question 20

Predict the products of the following reaction:

Accepted Answer

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

Exam 21: Organic Chemistry II: Reactions

Which combination of reagents would you use to prepare chlorobenzene (C6H5Cl)from benzene (C6H6)?

Which of the following statements is TRUE?

Write a balanced chemical reaction to represent the combustion of 2,2-dimethylpropane.

Which of the following statements is TRUE?

Which of the following statements is TRUE?

What are polymers?

Complete and balance the following addition reaction: CH3C ≡ CCH3 + 2Cl2 → ?

What is the product for the dehydration of CH3CH2CH2OH?

Predict the correct mechanism and product for the following reaction:

Which of the following statements is TRUE?

Which of the following five substrates is the most likely to be the substrate in an SN2 reaction?

Determine the products of the following reaction:

What are addition polymers?

Why doesn't benzene typically undergo addition reactions like the alkenes do?

Give the organic product of the following reaction. +CH3OH⟶H2SO4+ \mathrm { CH } _ { 3 } \mathrm { OH } \stackrel { \mathrm { H } _ { 2 } \mathrm { SO } _ { 4 } } { \longrightarrow }+CH3​OH⟶H2​SO4​​

Draw a clear mechanism for E1 elimination reactions.Make sure to indicate each step of the mechanism (if there is more than one)as well as to use arrows to show the electron flow.

Which of the following statements is TRUE?

Which is the strongest organic acid?

Which of the following statements is TRUE?

Predict the products of the following reaction:

Units of Measurement for Physical and Chemical Change

Atoms and Elements

Molecules,compounds,and Nomenclature

Chemical Reactions and Stoichiometry

Gases

Thermochemistry

The Quantum-Mechanical Model of the Atom

Periodic Properties of the Elements

Chemical Bonding I: Lewis Theory

Chemical Bonding II: Molecular Shapes, valence Bond Theory, and Molecular Orbital Theory

Liquids, solids, and Intermolecular Forces

Solutions

Chemical Kinetics

Chemical Equilibrium

Acids and Bases

Aqueous Ionic Equilibrium

Gibbs Energy and Thermodynamics

Electrochemistry

Radioactivity and Nuclear Chemistry

Organic Chemistry I: Structures

Biochemistry

Chemistry of the Nonmetals

Metals and Metallurgy

Transition Metals and Coordination Compounds

Filters

Which combination of reagents would you use to prepare chlorobenzene (C₆H₅Cl)from benzene (C₆H₆)?

Complete and balance the following addition reaction: CH₃C ≡ CCH₃ + 2Cl₂ → ?

What is the product for the dehydration of CH₃CH₂CH₂OH?

Which of the following five substrates is the most likely to be the substrate in an S_N² reaction?