Question 1

Which of the following molecules can tautomerize?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these 
A) I 
B) II 
C) III 
D) IV 
E) All of these E

Question 2

Butyl lithium reacts with the following acetyl bromide via a nucleophilic addition step.Provide the omitted mechanism arrows,and draw the missing product in the box.

Accepted Answer

The answer of Butyl lithium reacts with the following acetyl...

Question 3

The following carbocation undergoes a 1,2-alkyl shift.Draw the mechanism,and give the products of this shift.

Accepted Answer

The answer of The following carbocation undergoes a 1,2-alkyl shift.Draw...

Question 4

Which of the following is not true about a nucleophile elimination step?

Accepted Answer

A) A leaving group leaves. 
B) A multiple bond is formed. 
C) Only one product is formed. 
D) Electrons move from electron-rich to electron-poor parts of a molecule. 
E) Two mechanism arrows are used. 
A) A leaving group leaves. 
B) A multiple bond is formed. 
C) Only one product is formed. 
D) Electrons move from electron-rich to electron-poor parts of a molecule. 
E) Two mechanism arrows are used.

Question 5

What is the most likely mechanism for the following reaction?

Accepted Answer

A) SN2 
B) E2 
C) Electrophilic addition 
D) 1,2 methyl shift 
E) Nucleophilic addition 
A) SN2 
B) E2 
C) Electrophilic addition 
D) 1,2 methyl shift 
E) Nucleophilic addition

Question 6

The two following molecules can react via a coordination step.Draw the mechanism for this step and the resulting product.Also label the nucleophile and the electrophile.

Accepted Answer

The answer of The two following molecules can react via...

Question 7

Which of the following mechanism steps is most energetically favorable?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 8

Indicate which mechanism step is shown below,and draw the expected product(s).

Accepted Answer

Nucleophil

Question 9

The two following species can react via an electrophilic addition step.Draw the mechanism arrows for this step,give the expected product,and label the nucleophile and the electrophile.

Accepted Answer

The answer of The two following species can react via...

Question 10

The two following species can react via an SN2 mechanism.Fill in the mechanism arrows,and supply the expected products.

Accepted Answer

Question 11

Which of the following is not true about Grignard reagents?

Accepted Answer

A) They include a metal directly bonded to a carbon. 
B) They tend to be electrophiles. 
C) They are useful for forming new carbon-carbon bonds. 
D) They consist of a highly polar bond. 
E) They are organometallic compounds. 
A) They include a metal directly bonded to a carbon. 
B) They tend to be electrophiles. 
C) They are useful for forming new carbon-carbon bonds. 
D) They consist of a highly polar bond. 
E) They are organometallic compounds.

Question 12

In the following reaction,identify all electron-rich and electron-poor sites in the starting materials,and supply the missing mechanism arrows required to form the given product.

Accepted Answer

The answer of In the following reaction,identify all electron-rich and...

Question 13

Which of the following is not true about Lewis bases?

Accepted Answer

A) They donate electron density. 
B) They often bear a negative charge. 
C) They attack electron-poor sites. 
D) They tend to be electron rich. 
E) They tend to be electrophiles. 
A) They donate electron density. 
B) They often bear a negative charge. 
C) They attack electron-poor sites. 
D) They tend to be electron rich. 
E) They tend to be electrophiles.

Question 14

The following mechanism step is ________.

Accepted Answer

A) Heterolysis 
B) Coordination 
C) Nucleophile elimination 
D) E2 
E) Electrophile elimination 
A) Heterolysis 
B) Coordination 
C) Nucleophile elimination 
D) E2 
E) Electrophile elimination

Question 15

Which of the following is true about spectator ions?

Accepted Answer

A) They can be disregarded when drawing mechanisms. 
B) They are located in group 4A. 
C) They are highly insoluble. 
D) They are great targets for nucleophiles. 
E) They are highly reactive species. 
A) They can be disregarded when drawing mechanisms. 
B) They are located in group 4A. 
C) They are highly insoluble. 
D) They are great targets for nucleophiles. 
E) They are highly reactive species.

Question 16

The two following molecules can react via a nucleophilic addition.Draw the mechanism arrows for this step,and give the products.

Accepted Answer

The answer of The two following molecules can react via...

Question 17

Which of the following is an SN2 step?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 18

Which of the following is the carbocation most likely formed after a 1,2-hydride shift?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these 
A) I 
B) II 
C) III 
D) IV 
E) None of these

Question 19

For each of the five following mechanism steps,name the step being shown.Choose from the following: proton transfer,SN2,coordination,heterolysis,E2,nucleophilic addition,nucleophile elimination,electrophilic addition,electrophile elimination,carbocation rearrangement,or none of the above.

Accepted Answer

Nucleophilic additio

Question 20

The two following species can react via an SN2 mechanism.Fill in the mechanism arrows,and supply the expected products.

Accepted Answer

Exam 9: An Overview of the Most Common Elementary Steps

Which of the following molecules can tautomerize?

Butyl lithium reacts with the following acetyl bromide via a nucleophilic addition step.Provide the omitted mechanism arrows,and draw the missing product in the box.

The following carbocation undergoes a 1,2-alkyl shift.Draw the mechanism,and give the products of this shift.

Which of the following is not true about a nucleophile elimination step?

What is the most likely mechanism for the following reaction?

The two following molecules can react via a coordination step.Draw the mechanism for this step and the resulting product.Also label the nucleophile and the electrophile.

Which of the following mechanism steps is most energetically favorable?

Indicate which mechanism step is shown below,and draw the expected product(s).

The two following species can react via an electrophilic addition step.Draw the mechanism arrows for this step,give the expected product,and label the nucleophile and the electrophile.

The two following species can react via an SN2 mechanism.Fill in the mechanism arrows,and supply the expected products.

Which of the following is not true about Grignard reagents?

In the following reaction,identify all electron-rich and electron-poor sites in the starting materials,and supply the missing mechanism arrows required to form the given product.

Which of the following is not true about Lewis bases?

The following mechanism step is ________.

Which of the following is true about spectator ions?

The two following molecules can react via a nucleophilic addition.Draw the mechanism arrows for this step,and give the products.

Which of the following is an SN2 step?

Which of the following is the carbocation most likely formed after a 1,2-hydride shift?

For each of the five following mechanism steps,name the step being shown.Choose from the following: proton transfer,SN2,coordination,heterolysis,E2,nucleophilic addition,nucleophile elimination,electrophilic addition,electrophile elimination,carbocation rearrangement,or none of the above.

The two following species can react via an SN2 mechanism.Fill in the mechanism arrows,and supply the expected products.

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 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

Nucleophilic Additionelimination Reactions 2: Weak 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 two following species can react via an S_N2 mechanism.Fill in the mechanism arrows,and supply the expected products.

Which of the following is an S_N2 step?

For each of the five following mechanism steps,name the step being shown.Choose from the following: proton transfer,S_N2,coordination,heterolysis,E2,nucleophilic addition,nucleophile elimination,electrophilic addition,electrophile elimination,carbocation rearrangement,or none of the above.

The two following species can react via an S_N2 mechanism.Fill in the mechanism arrows,and supply the expected products.