Question 1

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 2

List the following compounds in order of increasing reactivity in an SN1 reaction.
CH3Br, CH3CH2CH2I, (CH3)3CI, CH3CHBrCH3, CH3CHICH3

Accepted Answer

CH₃Br < CH₃C

Question 3

Rank the species below in order of leaving group capabilities in SN2 reactions (worst leaving group to best):
CH3O-, H2O, C6H5SO3-, H2N-.

Accepted Answer

H₂N^- < CH₃O^- <

Question 4

Give the mechanism including the transition state.

Accepted Answer

The answer of Give the mechanism including the transition state....

Question 5

Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

Accepted Answer

A) reaction products when CH3I is used as the substrate 
B) reaction products when (CH3)3CCH2I is used as substrate 
C) the stereochemistry of nucleophilic substitutions 
D) the effect of nucleophile concentration on rate 
A) reaction products when CH3I is used as the substrate 
B) reaction products when (CH3)3CCH2I is used as substrate 
C) the stereochemistry of nucleophilic substitutions 
D) the effect of nucleophile concentration on rate

Question 6

Which of the following alkyl bromides is likely to undergo rearrangement by a 1, 2-methyl shift?

Accepted Answer

A) benzyl bromide 
B) 2-bromo-3-ethylpentane 
C) 3-bromo-3-methylpentane 
D) 2-bromo-3, 3-dimethylpentane 
E) 3-bromo-2, 3-dimethylpentane 
A) benzyl bromide 
B) 2-bromo-3-ethylpentane 
C) 3-bromo-3-methylpentane 
D) 2-bromo-3, 3-dimethylpentane 
E) 3-bromo-2, 3-dimethylpentane

Question 7

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 8

Which of the following species is the least nucleophilic?

Accepted Answer

A) (CH3)3CO- 
B) H2O 
C) (CH3)3N 
D) BF3 
E) CN- 
A) (CH3)3CO- 
B) H2O 
C) (CH3)3N 
D) BF3 
E) CN-

Question 9

Which of the following statements is generally true for SN1 reactions?

Accepted Answer

A) Complete inversion of configuration occurs. 
B) These reactions are favored by nonpolar solvents. 
C) These reactions are favored by polar solvents. 
D) Reaction rates depend only on the concentration of the nucleophile. 
E) The mechanism is a one-step back attack. 
A) Complete inversion of configuration occurs. 
B) These reactions are favored by nonpolar solvents. 
C) These reactions are favored by polar solvents. 
D) Reaction rates depend only on the concentration of the nucleophile. 
E) The mechanism is a one-step back attack.

Question 10

Provide a detailed, stepwise mechanism for the reaction below.
(CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

Accepted Answer

Question 11

Identify the strongest nucleophile in an SN2 reaction.

Accepted Answer

A) isopropoxide ion 
B) tert-butoxide ion 
C) ethoxide ion 
D) tert-pentoxide ion 
A) isopropoxide ion 
B) tert-butoxide ion 
C) ethoxide ion 
D) tert-pentoxide ion

Question 12

A student attempted to prepare 1-chlorobutane by treating 1-butanol with NaCl in acetone. Was the student successful? Explain.

Accepted Answer

The student was unsuccessful. The reacti

Question 13

Which of the following solvents is aprotic?

Accepted Answer

A) CH3CH2OH 
B) CH3CH2CH2NH2 
C) CH3CH2OCH2CH3 
D) CH3CH2NHCH3 
E)    
A) CH3CH2OH 
B) CH3CH2CH2NH2 
C) CH3CH2OCH2CH3 
D) CH3CH2NHCH3 
E)

Question 14

Give the mechanism including the transition state.

Accepted Answer

The answer of Give the mechanism including the transition state....

Question 15

Identify the mechanism. .

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) none of the above 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) none of the above

Question 16

Which of the following is the rate law for SN1 mechanisms?

Accepted Answer

A) Rate = k[Alkyl Halide] [Nucleophile] 
B) Rate = k[Nucleophile] 
C) Rate = k[Alkyl Halide] 
D) Rate = k[Alkyl Halide] [Nucleophile] + k2[Alkyl Halide] 
E) Rate = k1[Alkyl Halide] + k2[Nucleophile] 
A) Rate = k[Alkyl Halide] [Nucleophile] 
B) Rate = k[Nucleophile] 
C) Rate = k[Alkyl Halide] 
D) Rate = k[Alkyl Halide] [Nucleophile] + k2[Alkyl Halide] 
E) Rate = k1[Alkyl Halide] + k2[Nucleophile]

Question 17

Which of the following factors has no effect on the rate of SN1 reactions?

Accepted Answer

A) the nature of the alkyl halide 
B) the nature of the leaving group 
C) the concentration of the alkyl halide 
D) the concentration of the nucleophile 
E) the value of the rate constant 
A) the nature of the alkyl halide 
B) the nature of the leaving group 
C) the concentration of the alkyl halide 
D) the concentration of the nucleophile 
E) the value of the rate constant

Question 18

Which of the following correctly describes SAM, a biological methylating agent?

Accepted Answer

A) It contains a Cl bonded to a 1° carbon. 
B) It contains a methyl group bonded to a positively charged sulfur atom. 
C) It contains a methyl ether. 
D) it contains a methyl group bonded to an aromatic ring. 
E) It contains a Br bonded to a phosphorus atom. 
A) It contains a Cl bonded to a 1° carbon. 
B) It contains a methyl group bonded to a positively charged sulfur atom. 
C) It contains a methyl ether. 
D) it contains a methyl group bonded to an aromatic ring. 
E) It contains a Br bonded to a phosphorus atom.

Question 19

The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone. Why?

Accepted Answer

A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture. 
B) The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
C) The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
D) The solvent which contains a greater percentage of water is less polar, and this destabilizes the tert-butyl chloride. 
E) none of the above 
A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture. 
B) The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
C) The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. 
D) The solvent which contains a greater percentage of water is less polar, and this destabilizes the tert-butyl chloride. 
E) none of the above

Question 20

Give the name(s)of the product(s)of the SN1 reaction of 3-bromo-2,2-dimethylbutane with water.

Accepted Answer

A) 2,2-dimethyl-1-butanol 
B) 3,3-dimethyl-2-butanol 
C) 3,3-dimethyl-1-butanol 
D) 2,3-dimethyl-2-butanol 
E) 2,3-dimethyl-1-butanol 
A) 2,2-dimethyl-1-butanol 
B) 3,3-dimethyl-2-butanol 
C) 3,3-dimethyl-1-butanol 
D) 2,3-dimethyl-2-butanol 
E) 2,3-dimethyl-1-butanol

Exam 9: Substitution Reactions of Alkyl Halides

Provide the major organic product(s)in the reaction below.

List the following compounds in order of increasing reactivity in an SN1 reaction. CH3Br, CH3CH2CH2I, (CH3)3CI, CH3CHBrCH3, CH3CHICH3

Rank the species below in order of leaving group capabilities in SN2 reactions (worst leaving group to best): CH3O-, H2O, C6H5SO3-, H2N-.

Give the mechanism including the transition state.

Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

Which of the following alkyl bromides is likely to undergo rearrangement by a 1, 2-methyl shift?

Provide the major organic product(s)in the reaction below.

Which of the following species is the least nucleophilic?

Which of the following statements is generally true for SN1 reactions?

Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

Identify the strongest nucleophile in an SN2 reaction.

A student attempted to prepare 1-chlorobutane by treating 1-butanol with NaCl in acetone. Was the student successful? Explain.

Which of the following solvents is aprotic?

Give the mechanism including the transition state.

Identify the mechanism. .

Which of the following is the rate law for SN1 mechanisms?

Which of the following factors has no effect on the rate of SN1 reactions?

Which of the following correctly describes SAM, a biological methylating agent?

The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone. Why?

Give the name(s)of the product(s)of the SN1 reaction of 3-bromo-2,2-dimethylbutane with water.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Alpha Carbon of Carbonyl Compounds

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

List the following compounds in order of increasing reactivity in an S_N1 reaction. CH₃Br, CH₃CH₂CH₂I, (CH₃)₃CI, CH₃CHBrCH₃, CH₃CHICH₃

Rank the species below in order of leaving group capabilities in S_N2 reactions (worst leaving group to best): CH₃O^-, H₂O, C₆H₅SO₃^-, H₂N^-.

Which of the following statements is generally true for S_N1 reactions?

Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CN + I^-

Identify the strongest nucleophile in an S_N2 reaction.

Which of the following is the rate law for S_N1 mechanisms?

Which of the following factors has no effect on the rate of S_N1 reactions?

Give the name(s)of the product(s)of the S_N1 reaction of 3-bromo-2,2-dimethylbutane with water.