Question 1

Which of the following mechanistic steps represents a nucleophilic attack?

Accepted Answer

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

Question 2

Does a reaction with a positive ∆S and a negative ∆H favor reactants or products?

Accepted Answer

The answer of Does a reaction with a positive ∆S...

Question 3

Melphalan, a drug used in chemotherapy, reacts with itself in the body before binding with its target, as illustrated in the mechanism below. Which two patterns of arrow pushing are seen in this reaction?

Accepted Answer

Nucleophil

Question 4

Identify the nucleophilic and electrophilic sites in the substrate and reagent of the following reaction.

Accepted Answer

@#IMG-DLM&_TB4454_00 6.10 Desc

Question 5

Identify the nucleophilic atom in the following molecule, Me3P.

Accepted Answer

A)  P 
B)  C 
C)  H 
D)  Me 
A)  P 
B)  C 
C)  H 
D)  Me

Question 6

Which of the following energy diagrams is of a reaction with one transition state?

Accepted Answer

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

Question 7

What pattern of curved arrow pushing is the second step of this reaction?

Accepted Answer

A)  proton transfer 
B)  loss of leaving group 
C)  nucleophilic attack 
D)  rearrangement 
A)  proton transfer 
B)  loss of leaving group 
C)  nucleophilic attack 
D)  rearrangement

Question 8

Will the following cation undergo rearrangement?
SHAPE \* MERGEFORMAT

Accepted Answer

The answer of Will the following cation undergo rearrangement?
SHAPE \*...

Question 9

Identify the sequence of curved arrows (electron movement) in the steps of the following reaction.

Accepted Answer

A)  proton transfer, proton transfer 
B)  proton transfer, loss of leaving group 
C)  nucleophilic attack, proton transfer 
D)  proton transfer, nucleophilic attack 
A)  proton transfer, proton transfer 
B)  proton transfer, loss of leaving group 
C)  nucleophilic attack, proton transfer 
D)  proton transfer, nucleophilic attack

Question 10

Which of the following is hydride?

Accepted Answer

A)  H+ 
B)  H 
C)  H− 
D)  H2 
A)  H+ 
B)  H 
C)  H− 
D)  H2

Question 11

Draw the most likely structure of the following cation after it has rearranged.

Accepted Answer

The answer of Draw the most likely structure of the...

Question 12

Identify the electrophilic site in the following molecule, CH3CH2NHCH2CH3.

Accepted Answer

A)  H 
B)  N 
C)  CH2 
D)  CH3 
E)  there is no electrophilic site 
A)  H 
B)  N 
C)  CH2 
D)  CH3 
E)  there is no electrophilic site

Question 13

Draw curved arrows for each step of the following reaction.

Accepted Answer

@#IMG-DLM&_TB4454_00 6.10 Desc

Question 14

Using Table 6.1, which of the following is the enthalpy change of the following reaction under standard conditions?

Accepted Answer

A)  -8 kJ/mol 
B)  +8 kJ/mol 
C)  -506 kJ/mol 
D)  +63 kJ/mol 
A)  -8 kJ/mol 
B)  +8 kJ/mol 
C)  -506 kJ/mol 
D)  +63 kJ/mol

Question 15

In a heterolytic bond cleavage, ____ are formed.

Accepted Answer

A)  ions 
B)  radicals 
C)  only cations 
D)  only anions 
A)  ions 
B)  radicals 
C)  only cations 
D)  only anions

Question 16

Identify the electrophilic site in the following molecule.

Accepted Answer

SHAPE \* M

Question 17

Which of the following describes the effect of a catalyst on a reaction?

Accepted Answer

A)  It lowers the free energy of the products. 
B)  It makes the reactants less stable. 
C)  It changes the equilibrium constant. 
D)  It lowers the energy of activation. 
A)  It lowers the free energy of the products. 
B)  It makes the reactants less stable. 
C)  It changes the equilibrium constant. 
D)  It lowers the energy of activation.

Question 18

Which of the following would you expect to have the most negative ∆S?

Accepted Answer

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

Question 19

Which of the following energy diagrams is of a reaction with one intermediate?

Accepted Answer

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

Question 20

What pattern of curved arrow pushing is the second step of this reaction?

Accepted Answer

A)  proton transfer 
B)  loss of leaving group 
C)  nucleophilic attack 
D)  rearrangement 
A)  proton transfer 
B)  loss of leaving group 
C)  nucleophilic attack 
D)  rearrangement

Exam 6: Chemical Reactivity and Mechanisms

Which of the following mechanistic steps represents a nucleophilic attack?

Does a reaction with a positive ∆S and a negative ∆H favor reactants or products?

Melphalan, a drug used in chemotherapy, reacts with itself in the body before binding with its target, as illustrated in the mechanism below. Which two patterns of arrow pushing are seen in this reaction?

Identify the nucleophilic and electrophilic sites in the substrate and reagent of the following reaction.

Identify the nucleophilic atom in the following molecule, Me3P.

Which of the following energy diagrams is of a reaction with one transition state?

What pattern of curved arrow pushing is the second step of this reaction?

Will the following cation undergo rearrangement? SHAPE \* MERGEFORMAT

Identify the sequence of curved arrows (electron movement) in the steps of the following reaction.

Which of the following is hydride?

Draw the most likely structure of the following cation after it has rearranged.

Identify the electrophilic site in the following molecule, CH3CH2NHCH2CH3.

Draw curved arrows for each step of the following reaction.

Using Table 6.1, which of the following is the enthalpy change of the following reaction under standard conditions?

In a heterolytic bond cleavage, ____ are formed.

Identify the electrophilic site in the following molecule.

Which of the following describes the effect of a catalyst on a reaction?

Which of the following would you expect to have the most negative ∆S?

Which of the following energy diagrams is of a reaction with one intermediate?

What pattern of curved arrow pushing is the second step of this reaction?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Identify the nucleophilic atom in the following molecule, Me₃P.

Will the following cation undergo rearrangement? SHAPE \* MERGEFORMAT $Will the following cation undergo rearrangement? SHAPE \* MERGEFORMAT$ $Will the following cation undergo rearrangement? SHAPE \* MERGEFORMAT$

Identify the electrophilic site in the following molecule, CH₃CH₂NHCH₂CH₃.