Question 1

What is the major product of the following reaction?

Accepted Answer

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

Question 2

Which of the following compounds would undergo hydrolysis at the highest rate?

Accepted Answer

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

Question 3

The reaction below is an example of a(n)_________ reaction,which forms a(n)_________ as a product.

Accepted Answer

A) hydrolysis, ester 
B) aminolysis, amide 
C) alcoholysis, ester 
D) hydrolysis, carboxylic acid 
E) sulfonation, ester 
A) hydrolysis, ester 
B) aminolysis, amide 
C) alcoholysis, ester 
D) hydrolysis, carboxylic acid 
E) sulfonation, ester

Question 4

Propose a synthetic route to carry out the following transformation.

Accepted Answer

The answer of Propose a synthetic route to carry out...

Question 5

Rank the following in order of increasing reaction rate of hydrolysis.

Accepted Answer

A) 2 < 1 < 3 
B) 1 < 2 < 3 
C) 1 < 3 < 2 
D) 3 < 1 < 2 
E) 2 < 3 < 1 
A) 2 < 1 < 3 
B) 1 < 2 < 3 
C) 1 < 3 < 2 
D) 3 < 1 < 2 
E) 2 < 3 < 1

Question 6

Predict the major product of the following reaction sequence.

Accepted Answer

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

Question 7

Show how you would carry out the following synthesis.

Accepted Answer

The answer of Show how you would carry out the...

Question 8

What is the starting material of the following reaction sequence?

Accepted Answer

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

Question 9

What is the role of PCl3 in the following reaction?

Accepted Answer

A) It converts the carboxylic acid to an enolizable acid chloride. 
B) It acts as a base and deprotonates the α carbon. 
C) It converts the carboxylic acid to an acid bromide. 
D) It activates Br2 and forms a better nucleophile. 
E) It increases the rate of the reaction. 
A) It converts the carboxylic acid to an enolizable acid chloride. 
B) It acts as a base and deprotonates the α carbon. 
C) It converts the carboxylic acid to an acid bromide. 
D) It activates Br2 and forms a better nucleophile. 
E) It increases the rate of the reaction.

Question 10

What is the major driving force for the reaction below?

Accepted Answer

A) The product, an acid chloride, is more thermodynamically stable than a carboxylic acid. 
B) Chloride is a better nucleophile than hydroxide. 
C) The reaction is highly exothermic. 
D) Hydroxide is a better leaving group than chloride. 
E) The byproducts SO2 and HCl bubble out of solution irreversibly. 
A) The product, an acid chloride, is more thermodynamically stable than a carboxylic acid. 
B) Chloride is a better nucleophile than hydroxide. 
C) The reaction is highly exothermic. 
D) Hydroxide is a better leaving group than chloride. 
E) The byproducts SO2 and HCl bubble out of solution irreversibly.

Question 11

What is the rate-determining step in the reaction below?

Accepted Answer

A) Proton transfer 
B) Electrophilic addition 
C) Nucleophilic elimination 
D) Bimolecular nucleophilic substitution 
E) Nucleophilic addition 
A) Proton transfer 
B) Electrophilic addition 
C) Nucleophilic elimination 
D) Bimolecular nucleophilic substitution 
E) Nucleophilic addition

Question 12

What base would be the best choice to catalyze the reaction shown below?

Accepted Answer

A) N(C2H5)3 
B)    
C) NaOH 
D) NaO(CH2)3CH3 
E) NaOCH2CH3 
A) N(C2H5)3 
B)    
C) NaOH 
D) NaO(CH2)3CH3 
E) NaOCH2CH3

Question 13

What is the missing reagent needed to complete the synthesis below.

Accepted Answer

A)    
B)    
C) H2O 
D)    
E)    
A)    
B)    
C) H2O 
D)    
E)

Question 14

How many proton transfer steps occur in the mechanism for the reaction below?

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 4 
A) 0 
B) 1 
C) 2 
D) 3 
E) 4

Question 15

What is the rate-determining step in the mechanism for the following reaction?

Accepted Answer

A) Bimolecular nucleophilic substitution 
B) Coordination 
C) Nucleophile elimination 
D) Nucleophilic addition 
E) Proton transfer 
A) Bimolecular nucleophilic substitution 
B) Coordination 
C) Nucleophile elimination 
D) Nucleophilic addition 
E) Proton transfer

Question 16

Which of the following elementary steps is involved in the mechanism of the reaction shown below?

Accepted Answer

A) Coordination 
B) Proton transfer 
C) Bimolecular elimination 
D) Electrophilic addition 
E) Carbocation rearrangement 
A) Coordination 
B) Proton transfer 
C) Bimolecular elimination 
D) Electrophilic addition 
E) Carbocation rearrangement

Question 17

Fill in the missing starting material for the reaction below.

Accepted Answer

The answer of Fill in the missing starting material for...

Question 18

Determine the product of the following sequence of reactions.

Accepted Answer

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

Question 19

Show how the following could be synthesized from hexanoic acid.

Accepted Answer

The answer of Show how the following could be synthesized...

Question 20

Identify the N-terminus,the C-terminus,and the peptide bonds in the tripeptide below.

Accepted Answer

The answer of Identify the N-terminus,the C-terminus,and the peptide bonds...

Exam 23: Nucleophilic Additionelimination Reactions 2: Weak Nucleophiles

What is the major product of the following reaction?

Which of the following compounds would undergo hydrolysis at the highest rate?

The reaction below is an example of a(n)_________ reaction,which forms a(n)_________ as a product.

Propose a synthetic route to carry out the following transformation.

Rank the following in order of increasing reaction rate of hydrolysis.

Predict the major product of the following reaction sequence.

Show how you would carry out the following synthesis.

What is the starting material of the following reaction sequence?

What is the role of PCl3 in the following reaction?

What is the major driving force for the reaction below?

What is the rate-determining step in the reaction below?

What base would be the best choice to catalyze the reaction shown below?

What is the missing reagent needed to complete the synthesis below.

How many proton transfer steps occur in the mechanism for the reaction below?

What is the rate-determining step in the mechanism for the following reaction?

Which of the following elementary steps is involved in the mechanism of the reaction shown below?

Fill in the missing starting material for the reaction below.

Determine the product of the following sequence of reactions.

Show how the following could be synthesized from hexanoic acid.

Identify the N-terminus,the C-terminus,and the peptide bonds in the tripeptide below.

Atomic and Molecular Structure

Interchapter: Nomenclature 1-4

Interchapter 1molecular Orbital Theory and Chemical Reactions

Three-Dimensional Geometry,intermolecular Interactions,and Physical Properties

Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Isomerism 1: Conformational and Constitutional Isomers

Isomerism 2: Chirality,enantiomers,and Diastereomers

The Proton Transfer Reaction: an Introduction to Mechanisms,thermodynamics,and Charge Stability

An Overview of the Most Common Elementary Steps

An Introduction to Multistep Mechanisms: Sn1 and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 1: Competition Among Sn2,sn1,e2,and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis

Electrophilic Addition to Nonpolar Π Bonds 1: Addition of a Brønsted Acid

Electrophilic Addition to Nonpolar Π Bonds 2: Reactions Involving Cyclic Transition States

Organic Synthesis 1: Beginning Concepts

Orbital Interactions 2: Extended Π Systems,conjugation,and Aromaticity

Structure Determination 1: Ultravioletvisible and Infrared Spectroscopies

Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

Nucleophilic Addition to Polar Π Bonds 2: Addition of Weak Nucleophiles and Acid and Base Catalysis

Organic Synthesis 2: Intermediate Topics in Synthesis Design,and Useful Reduction and Oxidation Reactions

Nucleophilic Additionelimination Reactions 1: the General Mechanism Involving Strong Nucleophiles

Electrophilic Aromatic Substitution 1: Substitution on Benzene; Useful Accompanying Reactions

Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings

The Dielsalder Reaction and Other Pericyclic Reactions

Reactions Involving Free Radicals

Polymers

Filters

The reaction below is an example of a(n)_ reaction,which forms a(n)_ as a product.

What is the role of PCl₃ in the following reaction?