Question 1

Identify the possible products formed in the following substitution reaction. Please select all that apply.

Accepted Answer

A)  Product A 
B)  Product B 
C)  Product C 
D)  Product D 
A)  Product A 
B)  Product B 
C)  Product C 
D)  Product D A, B

Question 2

For the following reaction, pick out the major product:

Accepted Answer

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

Question 3

Match the chemical descriptors to the following molecules:
  
-Weak nucleophile

Accepted Answer

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

Question 4

For E2 elimination, pick out the descriptor which describes the stereochemical outcome of this elimination step.
A: syn-elimination
B: anti-elimination
C: orthogonal-elimination
D: syn-periplanar elimination
E: anti-periplanar elimination

Accepted Answer

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

Question 5

From the following reactions, pick out those which do NOT involve carbocation formation. Please select all that apply.

Accepted Answer

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

Question 6

What is the major product of the following reaction?

Accepted Answer

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

Question 7

Which of the following factors increase the rate of an SN1 reaction? Please select all that apply.

Accepted Answer

A)  Concentration of the aliphatic halide 
B)  Concentration of the nucleophile 
C)  Temperature 
D)  Non-polar aprotic solvent 
E)  Protic solvent
F) Polar aprotic solvent 
A)  Concentration of the aliphatic halide 
B)  Concentration of the nucleophile 
C)  Temperature 
D)  Non-polar aprotic solvent 
E)  Protic solvent
F) Polar aprotic solvent

Question 8

Match the chemical descriptors to the following molecules:
  
-Strong nucleophile

Accepted Answer

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

Question 9

Which of the following alkyl bromides can react with a base in an E2 elimination?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  D 
E)  None of these substrates are capable of E2 elimination 
A)  A 
B)  B 
C)  C 
D)  D 
E)  None of these substrates are capable of E2 elimination

Question 10

From the following anions, pick out the one which is the most stable leaving group.

Accepted Answer

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

Question 11

Match the chemical descriptors to the following molecules:
  
-Strong electrophile

Accepted Answer

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

Question 12

What product(s) would you expect from the following SN2 reaction?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  Equimolar mixture of A and B 
E)  Non-equimolar mixture of A and B 
A)  A 
B)  B 
C)  C 
D)  Equimolar mixture of A and B 
E)  Non-equimolar mixture of A and B

Question 13

Which of the following Newman projections depicts the most reactive conformation of ((2S,3R)-3-bromobutan-2-yl)benzene for undergoing E2 elimination?
 
Redraw instructions from author: The PhMe groups on the four structures below should be Ph (i.e. remove the Me)

Accepted Answer

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

Question 14

Match the chemical descriptors to the species in the following reaction:
  
--OTs

Accepted Answer

A)  Nucleophile 
B)  Leaving group   
C)  Electrophile 
D)  Counter ion 
A)  Nucleophile 
B)  Leaving group   
C)  Electrophile 
D)  Counter ion

Question 15

From the following chlorides, pick out those which are capable of undergoing SN1 or SN2 reactions. Please select all that apply.

Accepted Answer

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

Question 16

From the following benzylic chlorides, pick out the one which is the poorest electrophile for a SN1 reaction:

Accepted Answer

A)  A 
B)  B 
C)  C 
A)  A 
B)  B 
C)  C

Question 17

From the following bromides, pick out those which can react by a SN2 mechanism. Please select all that apply.

Accepted Answer

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

Question 18

What is the major product of the following E2 elimination?

Accepted Answer

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

Question 19

Identify the major elimination product formed under the following conditions:

Accepted Answer

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

Question 20

For a SN2 reaction, pick out the strongest nucleophile from the following species:
A: $ \mathrm{PhO} $
B: $ \mathrm{EtOH} $
C:$ \mathrm{MeCO}_{2}^{-} $
D: EtO
E: $ \mathrm{H}_{2} \mathrm{O} $

Accepted Answer

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

Exam 20: Halogenoalkanes: Substitution and Elimination Reactions

Identify the possible products formed in the following substitution reaction. Please select all that apply.

For the following reaction, pick out the major product:

Match the chemical descriptors to the following molecules: -Weak nucleophile

For E2 elimination, pick out the descriptor which describes the stereochemical outcome of this elimination step. A: syn-elimination B: anti-elimination C: orthogonal-elimination D: syn-periplanar elimination E: anti-periplanar elimination

From the following reactions, pick out those which do NOT involve carbocation formation. Please select all that apply.

What is the major product of the following reaction?

Which of the following factors increase the rate of an SN1 reaction? Please select all that apply.

Match the chemical descriptors to the following molecules: -Strong nucleophile

Which of the following alkyl bromides can react with a base in an E2 elimination?

From the following anions, pick out the one which is the most stable leaving group.

Match the chemical descriptors to the following molecules: -Strong electrophile

What product(s) would you expect from the following SN2 reaction?

Which of the following Newman projections depicts the most reactive conformation of ((2S,3R)-3-bromobutan-2-yl)benzene for undergoing E2 elimination? Redraw instructions from author: The PhMe groups on the four structures below should be Ph (i.e. remove the Me)

Match the chemical descriptors to the species in the following reaction: --OTs

From the following chlorides, pick out those which are capable of undergoing SN1 or SN2 reactions. Please select all that apply.

From the following benzylic chlorides, pick out the one which is the poorest electrophile for a SN1 reaction:

From the following bromides, pick out those which can react by a SN2 mechanism. Please select all that apply.

What is the major product of the following E2 elimination?

Identify the major elimination product formed under the following conditions:

For a SN2 reaction, pick out the strongest nucleophile from the following species: A: PhO \mathrm{PhO} PhO B: EtOH \mathrm{EtOH} EtOH C: MeCO2− \mathrm{MeCO}_{2}^{-} MeCO2−​ D: EtO E: H2O \mathrm{H}_{2} \mathrm{O} H2​O

Fundamentals

The Language of Organic Chemistry

Atomic Structure and Properties

Diatomic Molecules

Polyatomic Molecules

Solids

Acids and Bases

Gases

Reaction Kinetics

Molecular Spectroscopy

Analytical Chemistry

Molecular Characterisation

Energy and Thermochemistry

Entropy and Gibbs Energy

Electrochemistry

Phase Equilibrium and Solutions

Isomerism and Stereochemistry

Organic Reaction Mechanisms

Alkenes and Alkynes: Electrophilic Addition and Pericyclic Reactions

Benzene and Other Aromatic Compounds: Electrophilic Substitution Reactions

Aldehydes and Ketones: Nucleophilic Addition and Α-Substitution Reactions

Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution and Α-Substitution Reactions

Hydrogen

S-Block Chemistry

P-Block Chemistry

D-Block Chemistry

Filters

Which of the following factors increase the rate of an S_N1 reaction? Please select all that apply.

What product(s) would you expect from the following S_N2 reaction?

Match the chemical descriptors to the species in the following reaction: -^-OTs

From the following chlorides, pick out those which are capable of undergoing S_N1 or S_N2 reactions. Please select all that apply.

From the following benzylic chlorides, pick out the one which is the poorest electrophile for a S_N1 reaction:

From the following bromides, pick out those which can react by a S_N2 mechanism. Please select all that apply.

For a S_N2 reaction, pick out the strongest nucleophile from the following species: A: $\mathrm{PhO}$ B: $\mathrm{EtOH}$ C: $\mathrm{MeCO}_{2}^{-}$ D: EtO E: $\mathrm{H}_{2} \mathrm{O}$