Question 1

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

Accepted Answer

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

Question 2

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?

Accepted Answer

A) Rate = k [t-BuBr] 
B) Rate = k [t-BuBr][H2O] 
C) Rate = k [H2O] 
D) Rate = k [t-BuBr]2 
A) Rate = k [t-BuBr] 
B) Rate = k [t-BuBr][H2O] 
C) Rate = k [H2O] 
D) Rate = k [t-BuBr]2

Question 3

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 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 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

Question 6

Consider the pair of reactions below to answer the following question(s).
-The solvent in these reactions would be classified as ______ ________.

Accepted Answer

polar apro

Question 7

Classify each of the following species ,Place the letter of the choice in the blank to the left of the formula.
-________

Accepted Answer

A) an electrophile. 
B) a nucleophile. 
C) either an electrophile or a nucleophile. 
A) an electrophile. 
B) a nucleophile. 
C) either an electrophile or a nucleophile.

Question 8

Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide?

Accepted Answer

A) the reaction proceeds with inversion of configuration 
B) the rate is proportional to the concentration of sodium cyanide 
C) the rate is proportional to the concentration of (R)-2-bromobutane 
D) the rate of the reaction is independent of the identity of the solvent 
A) the reaction proceeds with inversion of configuration 
B) the rate is proportional to the concentration of sodium cyanide 
C) the rate is proportional to the concentration of (R)-2-bromobutane 
D) the rate of the reaction is independent of the identity of the solvent

Question 9

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 10

Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH?

Accepted Answer

A) methyl fluoride 
B) ethyl bromide 
C) 2-chloropropane 
D) tert-butyl bromide 
A) methyl fluoride 
B) ethyl bromide 
C) 2-chloropropane 
D) tert-butyl bromide

Question 11

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

Accepted Answer

The answer of Draw all of the chloroalkanes that undergo...

Question 12

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

Accepted Answer

The answer of Draw all of the chloroalkanes that undergo...

Question 13

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

Accepted Answer

The reaction proceeds in three steps:
1.

Question 14

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

Accepted Answer

A) The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack 
B) Carbocations are electrophilic 
C) The charged carbon atom of a carbocation has an unfilled valence shell 
D) Nucleophiles are Lewis acids 
A) The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack 
B) Carbocations are electrophilic 
C) The charged carbon atom of a carbocation has an unfilled valence shell 
D) Nucleophiles are Lewis acids

Question 15

What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide?

Accepted Answer

A) (R) 2-cyanohexane 
B) (S) 2-cyanohexane 
C) 1-hexene 
D) 2-hexene 
A) (R) 2-cyanohexane 
B) (S) 2-cyanohexane 
C) 1-hexene 
D) 2-hexene

Question 16

Which of the following is not a characteristic of SN1 reactions?

Accepted Answer

A) the electrophilic carbon undergoes inversion of stereochemistry 
B) the rate is proportional to the concentration of substrate 
C) the reaction proceeds faster in a more polar solvent 
D) the rate is independent of the concentration of nucleophile 
A) the electrophilic carbon undergoes inversion of stereochemistry 
B) the rate is proportional to the concentration of substrate 
C) the reaction proceeds faster in a more polar solvent 
D) the rate is independent of the concentration of nucleophile

Question 17

What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3)?

Accepted Answer

A) Rate = k [i-PrBr] 
B) Rate = k [i-PrBr]2 
C) Rate = k [NaOCH3] 
D) Rate = k [i-PrBr][NaOCH3] 
A) Rate = k [i-PrBr] 
B) Rate = k [i-PrBr]2 
C) Rate = k [NaOCH3] 
D) Rate = k [i-PrBr][NaOCH3]

Question 18

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

Accepted Answer

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

Question 19

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 20

Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH?

Accepted Answer

A) methyl chloride 
B) ethyl chloride 
C) 2-chloropropane 
D) tert-butyl chloride 
A) methyl chloride 
B) ethyl chloride 
C) 2-chloropropane 
D) tert-butyl chloride

Exam 9: Nucleophilic Substitution and Beta-Elimination

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

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?

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?

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

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

Consider the pair of reactions below to answer the following question(s). -The solvent in these reactions would be classified as ______ ________.

Classify each of the following species ,Place the letter of the choice in the blank to the left of the formula. -________

Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide?

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

Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH?

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

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

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

What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide?

Which of the following is not a characteristic of SN1 reactions?

What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3)?

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 methanol, CH3OH?

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

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an S_N1 mechanism?

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 is not a characteristic of S_N2 reactions?

Consider the pair of reactions below to answer the following question(s). -The solvent in these reactions would be classified as __.

Which of the following statements is not true regarding the S_N2 reaction of (R)-2-bromobutane with sodium cyanide?

Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH₃CH₂OH?

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

Which of the following is not a characteristic of S_N1 reactions?

What is the equation for the rate of formation of 2-methoxypropane, (CH₃CH(OCH₃)CH₃, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH₃)?

Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH₃OH?