Question 1

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I and II 
B)  II and III 
C)  III and IV 
D)  I and IV 
E)  All of the above 
A)  I and II 
B)  II and III 
C)  III and IV 
D)  I and IV 
E)  All of the above

Question 2

Draw the potential energy diagram that represents an exothermic reaction between a tertiary alkyl halide and methanol.Briefly explain your rationale.

Accepted Answer

The reaction is likely to occur via an S

Question 3

Consider the reaction of 2-chloro-2-methylpentane with sodium iodide.   Assuming no other changes,how would it affect the rate if one simultaneously doubled the concentration of 2-chloro-2-methylpentane and sodium iodide?

Accepted Answer

A)  No effect 
B)  It would double the rate. 
C)  It would triple the rate. 
D)  It would quadruple the rate. 
E)  It would increase the rate five times. 
A)  No effect 
B)  It would double the rate. 
C)  It would triple the rate. 
D)  It would quadruple the rate. 
E)  It would increase the rate five times.

Question 4

By analyzing the starting material and the product(s),the following reaction is possibly an example of what type of mechanism?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  More than one of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  More than one of the above

Question 5

Which would be formed in the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above

Question 6

The substitution mechanism whose rate depends primarily on the degree of steric hindrance around the leaving group is the _________.

Accepted Answer

the frequency of collisions be

Question 7

Which is the weakest nucleophile in polar aprotic solvents?

Accepted Answer

A)  I- 
B)  Br- 
C)  Cl- 
D)  F- 
E)  All of the above are equally strong nucleophiles,regardless of the type of solvent used 
A)  I- 
B)  Br- 
C)  Cl- 
D)  F- 
E)  All of the above are equally strong nucleophiles,regardless of the type of solvent used

Question 8

Which of the following would be most reactive in an SN2 reaction?

Accepted Answer

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

Question 9

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above

Question 10

Select the potential energy diagram that represents an exothermic (exergonic)reaction.

Accepted Answer

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

Question 11

What major product(s)are likely to be obtained from the following reaction?

Accepted Answer

A)  I,by predominantly SN2 
B)  II,by predominantly SN2 
C)  An equimolar mixture of I and II,by predominantly SN1. 
D)  III,by substitution of the alkyl group,rather than substitution of the chloro group. 
E)  Actually,none of these products are likely to be obtained as major products,because elimination will probably predominate,leading to the formation of an alkene. 
A)  I,by predominantly SN2 
B)  II,by predominantly SN2 
C)  An equimolar mixture of I and II,by predominantly SN1. 
D)  III,by substitution of the alkyl group,rather than substitution of the chloro group. 
E)  Actually,none of these products are likely to be obtained as major products,because elimination will probably predominate,leading to the formation of an alkene.

Question 12

Which alkyl halide,when treated with sodium ethoxide in ethanol,would afford a product mixture consisting of more than one elimination product?

Accepted Answer

A)  1-bromo-3,3-dimethylpentane 
B)  1-bromo-2,3-dimethylpentane 
C)  2-bromo-3,4-dimethylpentane 
D)  2-bromo-3,3-dimethylpentane 
E)  None of the above would yield more than one elimination product. 
A)  1-bromo-3,3-dimethylpentane 
B)  1-bromo-2,3-dimethylpentane 
C)  2-bromo-3,4-dimethylpentane 
D)  2-bromo-3,3-dimethylpentane 
E)  None of the above would yield more than one elimination product.

Question 13

By analyzing the starting material and the product,the following reaction is possibly an example of what type of mechanism(s)?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  More than one of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  More than one of the above

Question 14

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above

Question 15

Which of these species,acting in a protic solvent,exhibits greater nucleophilic activity than expected on the basis of its basicity?

Accepted Answer

A)  OH- 
B)  CH3O- 
C)  SH- 
D)  Cl- 
E)  H2O 
A)  OH- 
B)  CH3O- 
C)  SH- 
D)  Cl- 
E)  H2O

Question 16

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above

Question 17

The relative nucleophilicity of the halide ions in polar aprotic solvents is observed to be markedly different from that in protic solvents.Explain briefly.

Accepted Answer

The smaller,more highly electronegative

Question 18

Which alkyl chloride,though primary,is essentially unreactive in SN2 reactions?

Accepted Answer

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

Question 19

Reaction of sodium ethoxide with 1-bromopentane at 30 $\degree$C yields primarily:

Accepted Answer

A)  CH3CH2CH2CH=CH2 
B)  CH3CH2CH=CHCH3 
C)  CH3CH2CH2CH2CH3 
D)  CH3CH2CH2CH2CH2OH 
E)  CH3CH2CH2CH2CH2OCH2CH3 
A)  CH3CH2CH2CH=CH2 
B)  CH3CH2CH=CHCH3 
C)  CH3CH2CH2CH2CH3 
D)  CH3CH2CH2CH2CH2OH 
E)  CH3CH2CH2CH2CH2OCH2CH3

Question 20

Heating an alcoholic solution of sodium hydroxide and 1-bromopentane at 60 $\degree$C yields primarily:

Accepted Answer

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

Exam 6: Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

What would be the major product(s)of the following reaction?

Draw the potential energy diagram that represents an exothermic reaction between a tertiary alkyl halide and methanol.Briefly explain your rationale.

Consider the reaction of 2-chloro-2-methylpentane with sodium iodide. Assuming no other changes,how would it affect the rate if one simultaneously doubled the concentration of 2-chloro-2-methylpentane and sodium iodide?

By analyzing the starting material and the product(s),the following reaction is possibly an example of what type of mechanism?

Which would be formed in the following reaction?

The substitution mechanism whose rate depends primarily on the degree of steric hindrance around the leaving group is the _________.

Which is the weakest nucleophile in polar aprotic solvents?

Which of the following would be most reactive in an SN2 reaction?

What would be the major product(s)of the following reaction?

Select the potential energy diagram that represents an exothermic (exergonic)reaction.

What major product(s)are likely to be obtained from the following reaction?

Which alkyl halide,when treated with sodium ethoxide in ethanol,would afford a product mixture consisting of more than one elimination product?

By analyzing the starting material and the product,the following reaction is possibly an example of what type of mechanism(s)?

What would be the major product(s)of the following reaction?

Which of these species,acting in a protic solvent,exhibits greater nucleophilic activity than expected on the basis of its basicity?

What would be the major product(s)of the following reaction?

The relative nucleophilicity of the halide ions in polar aprotic solvents is observed to be markedly different from that in protic solvents.Explain briefly.

Which alkyl chloride,though primary,is essentially unreactive in SN2 reactions?

Reaction of sodium ethoxide with 1-bromopentane at 30 °\degree° C yields primarily:

Heating an alcoholic solution of sodium hydroxide and 1-bromopentane at 60 °\degree° C yields primarily:

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which of the following would be most reactive in an S_N2 reaction?

Which alkyl chloride,though primary,is essentially unreactive in S_N2 reactions?

Reaction of sodium ethoxide with 1-bromopentane at 30 $\degree$ C yields primarily:

Heating an alcoholic solution of sodium hydroxide and 1-bromopentane at 60 $\degree$ C yields primarily: