Question 1

The following energy diagram could represent an SN2 reaction.

Accepted Answer

A) True 
 B)False

Question 2

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 3

Consider the reaction below to answer the following question:   This reaction proceeds by an E1 mechanism.

Accepted Answer

A) True 
 B)False

Question 4

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 5

Which of the following statements is not true regarding SN2 reactions?

Accepted Answer

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

Question 6

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 7

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 8

What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH2Cl2?

Accepted Answer

A) it transfers 1-chlorooctane into the aqueous phase 
B) it transfers cyanide anion into the organic phase 
C) it makes water and dichloromethane miscible 
D) it transfers the sodium cation into the organic phase 
A) it transfers 1-chlorooctane into the aqueous phase 
B) it transfers cyanide anion into the organic phase 
C) it makes water and dichloromethane miscible 
D) it transfers the sodium cation into the organic phase

Question 9

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

Accepted Answer

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

Question 10

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 11

Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water?

Accepted Answer

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

Question 12

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?

Accepted Answer

A) 1-fluorohexane 
B) 1-chlorohexane 
C) 1-bromohexane 
D) 1-iodohexane 
A) 1-fluorohexane 
B) 1-chlorohexane 
C) 1-bromohexane 
D) 1-iodohexane

Question 13

Consider the pair of reactions below to answer the following question(s).
a.   
or
b.  
-The mechanism for these reactions is _______.

Accepted Answer

The answer of Consider the pair of reactions below to...

Question 14

HCl is the electrophile in the following reaction.

Accepted Answer

A) True 
 B)False

Question 15

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 16

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

Accepted Answer

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

Question 17

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

Accepted Answer

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

Question 18

Which of the following statements related to SN1 reactions is not true?

Accepted Answer

A) The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion 
B) The charged carbon atom of a carbocation has a complete octet of valence shell electrons 
C) Carbocations are Lewis acids 
D) Nucleophiles seek centers of low electron density 
A) The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion 
B) The charged carbon atom of a carbocation has a complete octet of valence shell electrons 
C) Carbocations are Lewis acids 
D) Nucleophiles seek centers of low electron density

Question 19

What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with methanol?

Accepted Answer

A) Rate = k [i-PrBr] 
B) Rate = k [i-PrBr]2 
C) Rate = k [CH3OH] 
D) Rate = k [i-PrBr][CH3OH] 
A) Rate = k [i-PrBr] 
B) Rate = k [i-PrBr]2 
C) Rate = k [CH3OH] 
D) Rate = k [i-PrBr][CH3OH]

Question 20

What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism?

Accepted Answer

A) Rate = k [BuCl] 
B) Rate = k [BuCl][NaI] 
C) Rate = k [NaI] 
D) Rate = k [BuCl]2 
A) Rate = k [BuCl] 
B) Rate = k [BuCl][NaI] 
C) Rate = k [NaI] 
D) Rate = k [BuCl]2

Exam 9: Nucleophilic Substitution and Beta-Elimination

The following energy diagram could represent an SN2 reaction.

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

Consider the reaction below to answer the following question: This reaction proceeds by an E1 mechanism.

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

Which of the following statements is not true regarding SN2 reactions?

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

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

What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH2Cl2?

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

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

Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water?

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?

Consider the pair of reactions below to answer the following question(s). a. or b. -The mechanism for these reactions is _______.

HCl is the electrophile in the following reaction.

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

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

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

Which of the following statements related to SN1 reactions is not true?

What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with methanol?

What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism?

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

The following energy diagram could represent an S_N2 reaction.

Which of the following statements is not true regarding S_N2 reactions?

What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH₂Cl₂?

Which of the following represents the transition state of the rate-determining step in the S_N1 reaction between tert-butyl chloride and water?

Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium azide, NaN₃?

Which of the following statements related to S_N1 reactions is not true?

What is the equation for the rate of formation of 2-methoxypropane, CH₃CH(OCH₃)CH₃, from the reaction of 2-bromopropane (i-PrBr) with methanol?

What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an S_N2 mechanism?