Question 1

The major product of the following reaction conditions will result from:

Accepted Answer

A)  SN2 
B)  SN1 
C)  E2 
D)  E1 
E)  there is no way to know 
A)  SN2 
B)  SN1 
C)  E2 
D)  E1 
E)  there is no way to know B

Question 2

What would be the major organic product of the following reaction?

Accepted Answer

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

Question 3

Which mechanism proceeds with inversion of configuration?

Accepted Answer

A)  bimolecular elimination (E2) 
B)  unimolecular elimination (E1) 
C)  unimolecular substitution (SN1) 
D)  bimolecular substitution (SN2) 
E)  free-radical halogenation 
A)  bimolecular elimination (E2) 
B)  unimolecular elimination (E1) 
C)  unimolecular substitution (SN1) 
D)  bimolecular substitution (SN2) 
E)  free-radical halogenation D

Question 4

For the transformation below,give the structure of the starting material.

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  Both B and C will provide the product shown. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  Both B and C will provide the product shown.

Question 5

For the transformation below,give the structure of the starting material.

Accepted Answer

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

Question 6

Rank the following according to their increasing reactivity with water.

Accepted Answer

A)  CH3Br 3CH2Br 3)3CBr 3)2CHBr 
B)  CH3Br 3CH2Br 3)2CHBr 3)3CBr 
C)  (CH3)3CBr 3)2CHBr 3CH2Br 3Br 
D)  All of these will react with water at the same rate. 
E)  None of the above will react with water. 
A)  CH3Br 3CH2Br 3)3CBr 3)2CHBr 
B)  CH3Br 3CH2Br 3)2CHBr 3)3CBr 
C)  (CH3)3CBr 3)2CHBr 3CH2Br 3Br 
D)  All of these will react with water at the same rate. 
E)  None of the above will react with water.

Question 7

Which would be true of the following reactions?

Accepted Answer

A)  cis would react faster 
B)  trans would react faster 
C)  cis and trans would react at the same rates 
D)  no reaction is expected under these conditions 
E)  the product shown would not be formed 
A)  cis would react faster 
B)  trans would react faster 
C)  cis and trans would react at the same rates 
D)  no reaction is expected under these conditions 
E)  the product shown would not be formed

Question 8

(S)-1-bromo-1-fluoroethane reacts with NaOMe to give:

Accepted Answer

A) 
    
B) 
  
C)  CH3CHFOCH3 
D)  CH3CHBrOCH3 
E)  CH3CH(OCH3)2 
A) 
    
B) 
  
C)  CH3CHFOCH3 
D)  CH3CHBrOCH3 
E)  CH3CH(OCH3)2

Question 9

Which one of the following would undergo E2 elimination most rapidly?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All would react at the same rate. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All would react at the same rate.

Question 10

To which side,if any,would the following equilibrium lie? (Do not consider any further reactions here.)

Accepted Answer

A)  to the left 
B)  to the right 
C)  equally to the right and left 
D)  there is no way to tell 
E)  this reaction cannot occur at all 
A)  to the left 
B)  to the right 
C)  equally to the right and left 
D)  there is no way to tell 
E)  this reaction cannot occur at all

Question 11

If the concentration of NaOH is doubled in the following reaction,what will happen to the reaction rate?

Accepted Answer

A)  no change 
B)  double 
C)  quadruple 
D)  cut in half 
E)  None of the above. 
A)  no change 
B)  double 
C)  quadruple 
D)  cut in half 
E)  None of the above.

Question 12

Predict the product of reaction of the following deuterated compound.

Accepted Answer

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

Question 13

Solvolysis of 2-bromo-2-methylpropane occurs through what mechanism?

Accepted Answer

A)  SN2 
B)  E1 
C)  E2 
D)  SN1 
E)  A and C 
A)  SN2 
B)  E1 
C)  E2 
D)  SN1 
E)  A and C

Question 14

Indicate the expected major product of the following reaction:

Accepted Answer

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

Question 15

Predict the major product of the following SN1 reaction:

Accepted Answer

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

Question 16

Which of the following is the least nucleophilic base?

Accepted Answer

A)  (CH3CH2)3N 
B) 
  
C) 
  
D) 
  
E) 
  
A)  (CH3CH2)3N 
B) 
  
C) 
  
D) 
  
E)

Question 17

Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH3?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above.

Question 18

For the transformation of norepinephrine to epinephrine (adrenaline),what is the likely mechanism?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  both A and B are likely 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  both A and B are likely

Question 19

Rank the following carbocations according to their increasing stability.

Accepted Answer

A)  A<B<C<D 
B)  A<C<B<D 
C)  C<A<B<D 
D)  A<C<D<B 
E)  None of the above. 
A)  A<B<C<D 
B)  A<C<B<D 
C)  C<A<B<D 
D)  A<C<D<B 
E)  None of the above.

Question 20

Predict the major product of the following reaction:

Accepted Answer

A) 
  only 
B) 
  
C) 
  only 
D) 
  
E) 
  and
  
A) 
  only 
B) 
  
C) 
  only 
D) 
  
E) 
  and

Exam 7: Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

The major product of the following reaction conditions will result from:

What would be the major organic product of the following reaction?

Which mechanism proceeds with inversion of configuration?

For the transformation below,give the structure of the starting material.

For the transformation below,give the structure of the starting material.

Rank the following according to their increasing reactivity with water.

Which would be true of the following reactions?

(S)-1-bromo-1-fluoroethane reacts with NaOMe to give:

Which one of the following would undergo E2 elimination most rapidly?

To which side,if any,would the following equilibrium lie? (Do not consider any further reactions here.)

If the concentration of NaOH is doubled in the following reaction,what will happen to the reaction rate?

Predict the product of reaction of the following deuterated compound.

Solvolysis of 2-bromo-2-methylpropane occurs through what mechanism?

Indicate the expected major product of the following reaction:

Predict the major product of the following SN1 reaction:

Which of the following is the least nucleophilic base?

Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH3?

For the transformation of norepinephrine to epinephrine (adrenaline),what is the likely mechanism?

Rank the following carbocations according to their increasing stability.

Predict the major product of the following reaction:

Structure and Bonding in Organic Molecules

Structure and Reactivity: Acids and Bases,polar and Nonpolar Molecules

Reactions of Alkanes: Bond-Dissociation Energies,radical Halogenation,and Relative Reactivity

Cycloalkanes

Stereoisomers

Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution

Hydroxy of Functional Group: Alcohols: Properties,preparation,and Strategy of Synthesis

Further Reactions of Alcohols and the Chemistry of Ethers

Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure

Alkenes: Infrared Spectroscopy and Mass Spectrometry

Reactions to Alkenes

Alkynes: the Carbon

Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy Interlude

Benzene and Aromaticity: Electrophilic Aromatic Substitution

Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Aldehydes and Ketones: the Carbonyl Group

Enols,enolates,and the Aldol Condensation: A,b-Unsaturated Aldehydes and Ketones

Carboxylic Acids

Carboxylic Acid Derivatives

Amines and Their Derivatives: Functional Groups Containing Nitrogen

Chemistry of the Benzene Substituents: Alkylbenzenes,phenols,and Benzenamines

Ester Enolates and the Claisen Condensation: Synthesis of B-Dicarbonyl Compounds; Acyl Anion Equivalents

Carbohydrates: Polyfunctional Compounds in Nature

Heterocycles: Heteroatoms in Cyclic Organic Compounds

Amino Acids,peptides,proteins,and Nucleic Acids: Nitrogen-Containing Polymers in Nature

Filters

Predict the major product of the following S_N1 reaction:

Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH₃?