Question 1

What is(are) the major organic product(s) obtained from the following substitution reaction?

Accepted Answer

A)  only 1 
B)  only 2 
C)  only 3 
D)  a mixture of 1 and 2 
A)  only 1 
B)  only 2 
C)  only 3 
D)  a mixture of 1 and 2

Question 2

What is the best choice of reagent to perform the following transformation?

Accepted Answer

A)  H2SO4 
B)  H2O 
C)  NaOCH3 
D)  KOtBu 
A)  H2SO4 
B)  H2O 
C)  NaOCH3 
D)  KOtBu

Question 3

Which of the following anions is the most nucleophilic in polar aprotic solvents?

Accepted Answer

A)  F− 
B)  Cl− 
C)  Br− 
D)  I− 
A)  F− 
B)  Cl− 
C)  Br− 
D)  I−

Question 4

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 5

Which of the following is best set of conditions for the preparation of tert-butanol?

Accepted Answer

A)  tert-butyl fluoride in water 
B)  tert-butyl bromide in water 
C)  tert-butyl fluoride and NaOH in DMSO 
D)  tert-butyl bromide and NaOH in DMSO 
A)  tert-butyl fluoride in water 
B)  tert-butyl bromide in water 
C)  tert-butyl fluoride and NaOH in DMSO 
D)  tert-butyl bromide and NaOH in DMSO

Question 6

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl iodide and water leading to elimination?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 7

Which of the following statements is not true regarding SN1 reactions?

Accepted Answer

A)  A carbocation intermediate is formed. 
B)  The mechanism has only one step. 
C)  Polar, protic solvents are good choices for SN1 reactions. 
D)  The stereochemical outcome is racemization at the carbon bearing the leaving group. 
A)  A carbocation intermediate is formed. 
B)  The mechanism has only one step. 
C)  Polar, protic solvents are good choices for SN1 reactions. 
D)  The stereochemical outcome is racemization at the carbon bearing the leaving group.

Question 8

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 9

HCl is the electrophile in the following reaction.

Accepted Answer

A) True 
 B)False

Question 10

The first step in the mechanism for the following reaction would be the formation of a secondary carbocation.

Accepted Answer

A) True 
 B)False

Question 11

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol leading to elimination?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 12

Which of the following energy diagrams represents the course of an exothermic E1 reaction?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 13

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 14

The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?

Accepted Answer

A)  the rate remains the same 
B)  the rate decreases by a factor of 2 
C)  the rate increases by a factor of 2 
D)  the rate increases by a factor of 4 
A)  the rate remains the same 
B)  the rate decreases by a factor of 2 
C)  the rate increases by a factor of 2 
D)  the rate increases by a factor of 4

Question 15

Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 16

What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?

Accepted Answer

A)  (R) 1-cyano-4-methylhexane 
B)  (S) 1-cyano-4-methylhexane 
C)  (R) 4-methyl-1-hexene 
D)  (S) 4-methyl-1-hexene 
A)  (R) 1-cyano-4-methylhexane 
B)  (S) 1-cyano-4-methylhexane 
C)  (R) 4-methyl-1-hexene 
D)  (S) 4-methyl-1-hexene

Question 17

Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 18

In the following reaction the cyanide ion is both a nucleophile and a Lewis acid.

Accepted Answer

A) True 
 B)False

Question 19

Which of the following sets consists of only polar protic solvents?

Accepted Answer

A)  water, DMF, DMSO 
B)  acetic acid, methanol, water 
C)  DMSO, ethanol, acetonitrile 
D)  DMF, acetonitrile, DMSO 
A)  water, DMF, DMSO 
B)  acetic acid, methanol, water 
C)  DMSO, ethanol, acetonitrile 
D)  DMF, acetonitrile, DMSO

Question 20

Which of the following is not a characteristic of SN2 reactions?

Accepted Answer

A)  the electrophilic carbon undergoes inversion of stereochemistry 
B)  the rate is proportional to the concentration of substrate 
C)  the rate is proportional to the concentration of nucleophile 
D)  the rate is independent of the solvent 
A)  the electrophilic carbon undergoes inversion of stereochemistry 
B)  the rate is proportional to the concentration of substrate 
C)  the rate is proportional to the concentration of nucleophile 
D)  the rate is independent of the solvent

Exam 9: Nucleophilic Substitution and Beta-Elimination

What is(are) the major organic product(s) obtained from the following substitution reaction?

What is the best choice of reagent to perform the following transformation?

Which of the following anions is the most nucleophilic in polar aprotic solvents?

What is the major organic product obtained from the following reaction?

Which of the following is best set of conditions for the preparation of tert-butanol?

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl iodide and water leading to elimination?

Which of the following statements is not true regarding SN1 reactions?

What is the major organic product obtained from the following reaction?

HCl is the electrophile in the following reaction.

The first step in the mechanism for the following reaction would be the formation of a secondary carbocation.

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol leading to elimination?

Which of the following energy diagrams represents the course of an exothermic E1 reaction?

What is the major organic product obtained from the following reaction?

The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?

Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination?

What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?

Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3?

In the following reaction the cyanide ion is both a nucleophile and a Lewis acid.

Which of the following sets consists of only polar protic solvents?

Which of the following is not a characteristic of SN2 reactions?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

Which of the following statements is not true regarding S_N1 reactions?

The reaction of tert-butyl bromide, (CH₃)₃CBr, with methanol in an inert solvent proceeds by an S_N1 mechanism to give tert-butyl methyl ether, (CH₃)₃COCH₃. What is the effect of doubling the concentration of methanol on the rate of the reaction?

Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH₃?

Which of the following is not a characteristic of S_N2 reactions?