Question 1

Which of the following reactions would not result in the formation of a racemic mixture of products?

Accepted Answer

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

Question 2

Which of the following would not yield the alcohol shown below?

Accepted Answer

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

Question 3

With respect to direct and conjugate addition,which of the following statements is false?

Accepted Answer

A) Reversible addition of a nucleophile generally favors conjugate addition. 
B) Very strong nucleophiles often yield the kinetic product. 
C) The reaction pathway with the lowest activation energy leads to the thermodynamic product. 
D) Irreversible addition of a nucleophile favors the product that is formed most rapidly. 
E) The conjugate addition product is more stable. 
A) Reversible addition of a nucleophile generally favors conjugate addition. 
B) Very strong nucleophiles often yield the kinetic product. 
C) The reaction pathway with the lowest activation energy leads to the thermodynamic product. 
D) Irreversible addition of a nucleophile favors the product that is formed most rapidly. 
E) The conjugate addition product is more stable. C

Question 4

Which nucleophile would you expect to add reversibly to an α,β-unsaturated carbonyl?

Accepted Answer

A) NaBH4 
B) CH3Li 
C) CH3(CH2)3MgBr 
D) NaCN 
E) LiAlH4 
A) NaBH4 
B) CH3Li 
C) CH3(CH2)3MgBr 
D) NaCN 
E) LiAlH4

Question 5

Draw the product of the reaction below.

Accepted Answer

The answer of Draw the product of the reaction below....

Question 6

Devise a synthesis of the compound shown below starting with ethanol and using any other reagents necessary.Provide detailed mechanisms of all reactions used.

Accepted Answer

The answer of Devise a synthesis of the compound shown...

Question 7

Give one example of a hypothetical Grignard reagent that contains an incompatible functional group.

Accepted Answer

Students' answers should include a funct

Question 8

Propose a synthesis to carry out the following transformation,using any reagents necessary.Note: This may require more than one step!

Accepted Answer

The answer of Propose a synthesis to carry out the...

Question 9

Circle the two sites in the molecule below that are electron poor and susceptible to nucleophilic attack.

Accepted Answer

The answer of Circle the two sites in the molecule...

Question 10

Fill in the starting material needed to carry out the reaction below.

Accepted Answer

The answer of Fill in the starting material needed to...

Question 11

Which of the following compounds could be synthesized via more than one possible route using a Gilman reagent?

Accepted Answer

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

Question 12

Which of the following proposed syntheses could be used to produce the molecule shown below as the major product?

Accepted Answer

A)    
B)    
C)    
D)    
E) All of the above would be successful. 
A)    
B)    
C)    
D)    
E) All of the above would be successful.

Question 13

Which of the following is the correct order of reactivity for this set of nucleophiles?

Accepted Answer

A) (CH3CH2)2CuLi > CH3CH2MgBr > CH3CH2Li 
B) CH3CH2Li = CH3CH2MgBr > (CH3CH2)2CuLi 
C) (CH3CH2)2CuLi > CH3CH2Li > CH3CH2MgBr 
D) CH3CH2Li > CH3CH2MgBr > (CH3CH2)2CuLi 
E) CH3CH2MgBr > (CH3CH2)2CuLi > CH3CH2Li 
A) (CH3CH2)2CuLi > CH3CH2MgBr > CH3CH2Li 
B) CH3CH2Li = CH3CH2MgBr > (CH3CH2)2CuLi 
C) (CH3CH2)2CuLi > CH3CH2Li > CH3CH2MgBr 
D) CH3CH2Li > CH3CH2MgBr > (CH3CH2)2CuLi 
E) CH3CH2MgBr > (CH3CH2)2CuLi > CH3CH2Li

Question 14

Propose two syntheses of the following compound,each using a different Gilman reagent.

Accepted Answer

The answer of Propose two syntheses of the following compound,each...

Question 15

Which of the following solvents would be the best choice to use for the reduction of a ketone using LiAlH4?

Accepted Answer

A) Isopropanol 
B) Water 
C) Acetic acid 
D) Diethyl ether 
E) Ethanol 
A) Isopropanol 
B) Water 
C) Acetic acid 
D) Diethyl ether 
E) Ethanol

Question 16

From the two routes shown below,choose the one that would be best for carrying out the reduction.Explain your choice.

Accepted Answer

The first route would accomplish the des

Question 17

Which of the following correctly explains why LiAlH4 is a stronger reducing agent than NaBH4?

Accepted Answer

A) LiAlH4 has less steric hindrance than NaBH4. 
B) The electronegativity of Al is lower than that of B. 
C) The electronegativity of Li is higher than that of Na. 
D) Hydrogen has a greater partial positive charge in LiAlH4 than in NaBH4. 
E) The electronegativity difference between Li and H is greater than the difference between Na and H. 
A) LiAlH4 has less steric hindrance than NaBH4. 
B) The electronegativity of Al is lower than that of B. 
C) The electronegativity of Li is higher than that of Na. 
D) Hydrogen has a greater partial positive charge in LiAlH4 than in NaBH4. 
E) The electronegativity difference between Li and H is greater than the difference between Na and H.

Question 18

Which is more thermodynamically stable,the product of a conjugate addition or that of a direct addition? Give two specific reasons to support your answer.

Accepted Answer

The product of a conjugate addition is m

Question 19

Determine which of the following molecules is most susceptible to nucleophilic attack,and explain why.

Accepted Answer

@#IMG-DLM& is most susceptible to nucleo

Question 20

What is the major driving force for the mechanistic step shown below?

Accepted Answer

A) Stability of C   C bond 
B) Completing the octet around P 
C) Electron rich to electron poor 
D) Formation of strong P+F1F1F1S1F1F1F10OF1F1F1S1F1F1F10 bond 
E) Release of ring strain 
A) Stability of C   C bond 
B) Completing the octet around P 
C) Electron rich to electron poor 
D) Formation of strong P+F1F1F1S1F1F1F10OF1F1F1S1F1F1F10 bond 
E) Release of ring strain

Exam 19: Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

Which of the following reactions would not result in the formation of a racemic mixture of products?

Which of the following would not yield the alcohol shown below?

With respect to direct and conjugate addition,which of the following statements is false?

Which nucleophile would you expect to add reversibly to an α,β-unsaturated carbonyl?

Draw the product of the reaction below.

Devise a synthesis of the compound shown below starting with ethanol and using any other reagents necessary.Provide detailed mechanisms of all reactions used.

Give one example of a hypothetical Grignard reagent that contains an incompatible functional group.

Propose a synthesis to carry out the following transformation,using any reagents necessary.Note: This may require more than one step!

Circle the two sites in the molecule below that are electron poor and susceptible to nucleophilic attack.

Fill in the starting material needed to carry out the reaction below.

Which of the following compounds could be synthesized via more than one possible route using a Gilman reagent?

Which of the following proposed syntheses could be used to produce the molecule shown below as the major product?

Which of the following is the correct order of reactivity for this set of nucleophiles?

Propose two syntheses of the following compound,each using a different Gilman reagent.

Which of the following solvents would be the best choice to use for the reduction of a ketone using LiAlH4?

From the two routes shown below,choose the one that would be best for carrying out the reduction.Explain your choice.

Which of the following correctly explains why LiAlH4 is a stronger reducing agent than NaBH4?

Which is more thermodynamically stable,the product of a conjugate addition or that of a direct addition? Give two specific reasons to support your answer.

Determine which of the following molecules is most susceptible to nucleophilic attack,and explain why.

What is the major driving force for the mechanistic step shown 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 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

Which of the following solvents would be the best choice to use for the reduction of a ketone using LiAlH₄?

Which of the following correctly explains why LiAlH₄ is a stronger reducing agent than NaBH₄?