Question 1

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 B

Question 2

Which of the following reactions corresponds to a substitution?

Accepted Answer

A)  propene 1,2-dibromopropane 
B)  1-iodopropane propene 
C)  propene propane 
D)  1-iodopropane 1-bromopropane 
A)  propene 1,2-dibromopropane 
B)  1-iodopropane propene 
C)  propene propane 
D)  1-iodopropane 1-bromopropane D

Question 3

Which of the following anions is the best leaving group in an SN1 reaction?

Accepted Answer

A)  F- 
B)  HO- 
C)  NH2- 
D)  Cl- 
A)  F- 
B)  HO- 
C)  NH2- 
D)  Cl- D

Question 4

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of paris of electrons and the structure of reactive intermediates.

Accepted Answer

The reaction proceeds in three steps:
1.

Question 5

Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane?

Accepted Answer

A)  sodium methoxide 
B)  sodium ethoxide 
C)  sodium isoproxide 
D)  sodium tert-butoxide 
A)  sodium methoxide 
B)  sodium ethoxide 
C)  sodium isoproxide 
D)  sodium tert-butoxide

Question 6

Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

Accepted Answer

A)  dimethylsulfoxide 
B)  water 
C)  hexane 
D)  toluene, PhCH3 
A)  dimethylsulfoxide 
B)  water 
C)  hexane 
D)  toluene, PhCH3

Question 7

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

Accepted Answer

A)  3-methyl-1-pentyne 
B)  3-methyl-2-pentyne 
C)  1-propene + propyne 
D)  4-methyl-2-pentene 
A)  3-methyl-1-pentyne 
B)  3-methyl-2-pentyne 
C)  1-propene + propyne 
D)  4-methyl-2-pentene

Question 8

Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?

Accepted Answer

A)  tert-butyl fluoride and NaOCH3 in CH3OH 
B)  methanol and sodium tert-butoxide in tert-butanol 
C)  fluoromethane and sodium tert-butoxide in tert-butanol 
D)  tert-butyl bromide and CH3OH 
A)  tert-butyl fluoride and NaOCH3 in CH3OH 
B)  methanol and sodium tert-butoxide in tert-butanol 
C)  fluoromethane and sodium tert-butoxide in tert-butanol 
D)  tert-butyl bromide and CH3OH

Question 9

Which of the following energy diagrams represents the course of an exothermic SN1 reaction?

Accepted Answer

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

Question 10

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 11

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

Accepted Answer

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

Question 12

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 13

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

Accepted Answer

A)  only 1 
B)  only 2 
C)  only 1 and 2 
D)  1, 2 and 3 
A)  only 1 
B)  only 2 
C)  only 1 and 2 
D)  1, 2 and 3

Question 14

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

Accepted Answer

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

Question 15

Which of the following energy diagrams represents the course of an exothermic E2 reaction?

Accepted Answer

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

Question 16

Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?

Accepted Answer

A)  tert-butyl fluoride 
B)  tert-butyl chloride 
C)  tert-butyl bromide 
D)  tert-butyl iodide 
A)  tert-butyl fluoride 
B)  tert-butyl chloride 
C)  tert-butyl bromide 
D)  tert-butyl iodide

Question 17

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 18

Which of the following is the most nucleophilic?

Accepted Answer

A)  sodium ethoxide 
B)  acetic acid 
C)  methanol 
D)  water 
A)  sodium ethoxide 
B)  acetic acid 
C)  methanol 
D)  water

Question 19

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 20

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?

Accepted Answer

A)  acetic acid 
B)  ethanol 
C)  water 
D)  acetonitrile 
A)  acetic acid 
B)  ethanol 
C)  water 
D)  acetonitrile

Exam 9: Nucleophilic Substitution and Beta-Elimination

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

Which of the following reactions corresponds to a substitution?

Which of the following anions is the best leaving group in an SN1 reaction?

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of paris of electrons and the structure of reactive intermediates.

Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane?

Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

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

Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?

Which of the following energy diagrams represents the course of an exothermic SN1 reaction?

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?

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

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

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

Which of the following energy diagrams represents the course of an exothermic E2 reaction?

Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?

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

Which of the following is the most nucleophilic?

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

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?

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

Filters

Which of the following anions is the best leaving group in an S_N1 reaction?

Which of the following energy diagrams represents the course of an exothermic S_N1 reaction?

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

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN₃, proceed the fastest?