Question 1

By what mechanism is the following reaction likely to occur?

Accepted Answer

The answer of By what mechanism is the following reaction...

Question 2

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  H2S in water 
B)  H2S in DMSO 
C)  NaSH in water 
D)  NaSH in DMSO 
A)  H2S in water 
B)  H2S in DMSO 
C)  NaSH in water 
D)  NaSH in DMSO

Question 3

Which of the following is a protic solvent?

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 4

Which of the following compounds will undergo the fastest SN1 reaction? Explain your choice.

Accepted Answer

Compound IV. The car

Question 5

Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

Accepted Answer

The answer of Based upon the following energy diagram, is...

Question 6

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  NaOH in water 
B)  NaOH in ether 
C)  H2O 
D)  CH3OH 
A)  NaOH in water 
B)  NaOH in ether 
C)  H2O 
D)  CH3OH

Question 7

Which of the following is the rate equation for the following reaction?

Accepted Answer

A)  Rate = k[CH3CH2CH2CHBrCH3] 
B)  Rate = k[NaN3] 
C)  Rate = k[CH3CH2CH2CHBrCH3] [NaBr] 
D)  Rate = k[CH3CH2CH2CHBrCH3] [NaN3] 
E)  Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3] 
A)  Rate = k[CH3CH2CH2CHBrCH3] 
B)  Rate = k[NaN3] 
C)  Rate = k[CH3CH2CH2CHBrCH3] [NaBr] 
D)  Rate = k[CH3CH2CH2CHBrCH3] [NaN3] 
E)  Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3]

Question 8

Which of the following alkyl halides is essentially unreactive in an SN2 reaction?

Accepted Answer

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

Question 9

Which pattern of arrow pushing is associated with the first step in any dehydration reaction?

Accepted Answer

The answer of Which pattern of arrow pushing is associated...

Question 10

Predict the product(s) for the following SN1 reaction.

Accepted Answer

A)  Both I & IV 
B)  II 
C)  III 
D)  IV 
E)  Both II & III 
A)  Both I & IV 
B)  II 
C)  III 
D)  IV 
E)  Both II & III

Question 11

Is the geometry of the following alkene -- E, Z, or neither?

Accepted Answer

The answer of Is the geometry of the following alkene...

Question 12

Which of the following is a reasonable definition of a concerted reaction?

Accepted Answer

A)  a reaction in which bond breaking occurs first 
B)  a reaction in which all bond-breaking and bond-forming occurs at the same time 
C)  a reaction in which bond forming occurs first 
D)  a substitution reaction 
A)  a reaction in which bond breaking occurs first 
B)  a reaction in which all bond-breaking and bond-forming occurs at the same time 
C)  a reaction in which bond forming occurs first 
D)  a substitution reaction

Question 13

Draw the major product of the following reaction.

Accepted Answer

The answer of Draw the major product of the following...

Question 14

Which of the following is NOT a nucleophile?

Accepted Answer

A)  OH- 
B)  NH3 
C)  CH3OH 
D)  NH4+ 
E)  All of these 
A)  OH- 
B)  NH3 
C)  CH3OH 
D)  NH4+ 
E)  All of these

Question 15

Is the following more likely a nucleophile or a base?

Accepted Answer

The answer of Is the following more likely a nucleophile...

Question 16

Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.

Accepted Answer

The answer of Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane....

Question 17

Identify the type of elimination in an E2 mechanism.

Accepted Answer

A)  alpha elimination 
B)  beta elimination 
C)  gamma elimination 
D)  delta elimination 
E)  omega elimination 
A)  alpha elimination 
B)  beta elimination 
C)  gamma elimination 
D)  delta elimination 
E)  omega elimination

Question 18

Is the geometry of the following alkene -- E, Z, or neither?

Accepted Answer

The answer of Is the geometry of the following alkene...

Question 19

Which of the following compounds will undergo rearrangement during solvolysis reaction?

Accepted Answer

A)  3-iodo-5-methylheptane 
B)  3-iodo-2-methylheptane 
C)  3-iodo-3-methylheptane 
D)  3-iodoheptane 
E)  cis-1-iodo-3-methylcyclohexane 
A)  3-iodo-5-methylheptane 
B)  3-iodo-2-methylheptane 
C)  3-iodo-3-methylheptane 
D)  3-iodoheptane 
E)  cis-1-iodo-3-methylcyclohexane

Question 20

By what mechanism is the following reaction likely to occur?

Accepted Answer

S_N2 (major)

Exam 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

By what mechanism is the following reaction likely to occur?

Provide the reagents necessary to carry out the following conversion.

Which of the following is a protic solvent?

Which of the following compounds will undergo the fastest SN1 reaction? Explain your choice.

Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

Provide the reagents necessary to carry out the following conversion.

Which of the following is the rate equation for the following reaction?

Which of the following alkyl halides is essentially unreactive in an SN2 reaction?

Which pattern of arrow pushing is associated with the first step in any dehydration reaction?

Predict the product(s) for the following SN1 reaction.

Is the geometry of the following alkene -- E, Z, or neither?

Which of the following is a reasonable definition of a concerted reaction?

Draw the major product of the following reaction.

Which of the following is NOT a nucleophile?

Is the following more likely a nucleophile or a base?

Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.

Identify the type of elimination in an E2 mechanism.

Is the geometry of the following alkene -- E, Z, or neither?

Which of the following compounds will undergo rearrangement during solvolysis reaction?

By what mechanism is the following reaction likely to occur?

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

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

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

Which of the following compounds will undergo the fastest S_N1 reaction? Explain your choice.

Which of the following alkyl halides is essentially unreactive in an S_N2 reaction?

Predict the product(s) for the following S_N1 reaction.