Question 1

Which of the following SN2 reactions is the slowest?

Accepted Answer

A) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
B) CH3CH2CH2Cl + HO- → CH3CH2CH2OH + Cl- 
C) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
D) CH3CH2CH3F + HO- → CH3CH2CH2OH + F- 
E)    
A) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
B) CH3CH2CH2Cl + HO- → CH3CH2CH2OH + Cl- 
C) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
D) CH3CH2CH3F + HO- → CH3CH2CH2OH + F- 
E)

Question 2

Which of the following statements concerning SN2 reactions of alkyl halides is not correct?

Accepted Answer

A) The rate of reaction depends on the concentration of the nucleophile. 
B) The rate of reaction depends on the concentration of the alkyl halide. 
C) The rate of reaction of a particular alkyl bromide depends on the steric accessibility of the carbon of the C-Br bond. 
D) All alkyl iodides react more rapidly than all alkyl chlorides. 
E) The rate of reaction depends on the relative nucleophilicity of the nucleophile. 
A) The rate of reaction depends on the concentration of the nucleophile. 
B) The rate of reaction depends on the concentration of the alkyl halide. 
C) The rate of reaction of a particular alkyl bromide depends on the steric accessibility of the carbon of the C-Br bond. 
D) All alkyl iodides react more rapidly than all alkyl chlorides. 
E) The rate of reaction depends on the relative nucleophilicity of the nucleophile.

Question 3

Provide the structure of the major organic product of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 4

SN1 reactions usually proceed with

Accepted Answer

A) equal amounts of inversion and retention at the center undergoing substitution. 
B) slightly more inversion than retention at the center undergoing substitution. 
C) slightly more retention than inversion at the center undergoing substitution. 
D) complete inversion at the center undergoing substitution. 
E) complete retention at the center undergoing substitution. 
A) equal amounts of inversion and retention at the center undergoing substitution. 
B) slightly more inversion than retention at the center undergoing substitution. 
C) slightly more retention than inversion at the center undergoing substitution. 
D) complete inversion at the center undergoing substitution. 
E) complete retention at the center undergoing substitution.

Question 5

Which of the following is not a nucleophile?

Accepted Answer

A) CH3NH2 
B) PH3 
C) (+CH3) 
D)    
E)    
A) CH3NH2 
B) PH3 
C) (+CH3) 
D)    
E)

Question 6

Provide the major organic product(s)of the reaction shown.

Accepted Answer

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

Question 7

What is the major organic product of the following reaction?

Accepted Answer

A) 2,3-dimethyl-1-hexene 
B) 2,3-dimethyl-2-hexene 
C) 2-isopropyl-1-pentene 
D) (Z)-2,3-dimethyl-3-hexene 
E) (
E) -2,3-dimethyl-3-hexene 
A) 2,3-dimethyl-1-hexene 
B) 2,3-dimethyl-2-hexene 
C) 2-isopropyl-1-pentene 
D) (Z)-2,3-dimethyl-3-hexene 
E) (
E) -2,3-dimethyl-3-hexene

Question 8

Show the best way to prepare CH3OCH(CH3)2 by an SN2 reaction.

Accepted Answer

Question 9

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 10

What is the major product of the following reaction?

Accepted Answer

A) CH2   CHCH2CH   CH2 
B)    
C) CH2   CHCH   CHCH3 
D)    
E) CH2   CHCH2CH2CH2OH 
A) CH2   CHCH2CH   CH2 
B)    
C) CH2   CHCH   CHCH3 
D)    
E) CH2   CHCH2CH2CH2OH

Question 11

Provide the structure of the major organic product(s)of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 12

Which of the following iodides undergoes SN1 solvolysis in water the fastest?

Accepted Answer

A) 1-iodo-3-methylpentane 
B) 2-iodopentane 
C) 2-iodo-2-methylpentane 
D) 3-iodopentane 
E) 1-iodo-2,2-dimethylpentane 
A) 1-iodo-3-methylpentane 
B) 2-iodopentane 
C) 2-iodo-2-methylpentane 
D) 3-iodopentane 
E) 1-iodo-2,2-dimethylpentane

Question 13

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 14

When 2-bromo-3-methyl-1-phenylbutane is treated with sodium methoxide,why is the major product 3-methyl-1-phenyl-1-butene?

Accepted Answer

A) SN2 predominates over E2. 
B) E1 predominates over E2. 
C) The bulkiness of the methoxide results in the less substituted alkene. 
D) The newly formed double bond in this compound is conjugated with the phenyl ring. 
E) The less substituted alkene is always more stable than the more substituted alkene. 
A) SN2 predominates over E2. 
B) E1 predominates over E2. 
C) The bulkiness of the methoxide results in the less substituted alkene. 
D) The newly formed double bond in this compound is conjugated with the phenyl ring. 
E) The less substituted alkene is always more stable than the more substituted alkene.

Question 15

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 16

What is the most reactive alkyl halide for elimination reactions?

Accepted Answer

A) 1-chlorobutane 
B) 1-fluorobutane 
C) 1-iodobutane 
D) 1-bromobutane 
A) 1-chlorobutane 
B) 1-fluorobutane 
C) 1-iodobutane 
D) 1-bromobutane

Question 17

Which of the following is least likely to be found in the product mixture which results when 2-iodopentane reacts with sodium ethoxide in ethanol?

Accepted Answer

A) 1-ethoxypentane 
B) 2-ethoxypentane 
C) (Z)-2-pentene 
D) (
E) -2-pentene 
E) 1-pentene 
A) 1-ethoxypentane 
B) 2-ethoxypentane 
C) (Z)-2-pentene 
D) (
E) -2-pentene 
E) 1-pentene

Question 18

Identify the alkyl halide that reacts the fastest in an SN1 reaction.

Accepted Answer

A) 2-chloro-2-methylpropane 
B) 2-chlorobutane 
C) 1-chlorobutane 
D) chloromethane 
A) 2-chloro-2-methylpropane 
B) 2-chlorobutane 
C) 1-chlorobutane 
D) chloromethane

Question 19

What product results from the SN2 reaction between (R)-2-chloropentane and hydroxide?

Accepted Answer

A) (R)-2-pentanol 
B) (S)-2-pentanol 
C) racemic pentanol 
D) 1-pentanol 
E) 3-pentanol 
A) (R)-2-pentanol 
B) (S)-2-pentanol 
C) racemic pentanol 
D) 1-pentanol 
E) 3-pentanol

Question 20

Which of the following SN2 reactions is the fastest?

Accepted Answer

A)    
B) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
C)    
D) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
E) CH3CH2CH2I + H2O → CH3CH2CH2OH + HI 
A)    
B) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
C)    
D) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
E) CH3CH2CH2I + H2O → CH3CH2CH2OH + HI

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

Which of the following SN2 reactions is the slowest?

Which of the following statements concerning SN2 reactions of alkyl halides is not correct?

Provide the structure of the major organic product of the following reaction.

SN1 reactions usually proceed with

Which of the following is not a nucleophile?

Provide the major organic product(s)of the reaction shown.

What is the major organic product of the following reaction?

Show the best way to prepare CH3OCH(CH3)2 by an SN2 reaction.

Provide the major organic product of the following reaction.

What is the major product of the following reaction?

Provide the structure of the major organic product(s)of the following reaction.

Which of the following iodides undergoes SN1 solvolysis in water the fastest?

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

When 2-bromo-3-methyl-1-phenylbutane is treated with sodium methoxide,why is the major product 3-methyl-1-phenyl-1-butene?

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

What is the most reactive alkyl halide for elimination reactions?

Which of the following is least likely to be found in the product mixture which results when 2-iodopentane reacts with sodium ethoxide in ethanol?

Identify the alkyl halide that reacts the fastest in an SN1 reaction.

What product results from the SN2 reaction between (R)-2-chloropentane and hydroxide?

Which of the following SN2 reactions is the fastest?

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds: Nomenclature, physical Properties, and Structure

Isomers: the Arrangement of Atoms in Space

Alkenes: Structure,nomenclature,and an Introduction to Reactivity - Thermodynamics and Kinetics

The Reactions of Alkenes - the Stereochemistry of Addition Reactions

The Reactions of Alkynes - Introduction to Multistep Synthesis

Delocalized Electrons: Their Effect on Stability, pka, and the Products of a Reaction - Aromaticity and Electronic Effects: an Introduction to the Reactions of Benzene

Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Organometallic Compounds

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 Α-Carbon

Reactions of Benzene and Substituted Benzenes

More About Amines - Reactions of Heterocylic Compounds

The Organic Chemistry of Carbohydrates

Amino Acids,peptides,and Proteins

Catalysis in Organic Reactions and in Enzymatic Reactions

The Organic Chemistry of the Coenzymes, compounds Derived From Vitamins

The Organic Chemistry of the Metabolic Pathways

The Organic Chemistry of Lipids

The Chemistry of the Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Which of the following S_N2 reactions is the slowest?

Which of the following statements concerning S_N2 reactions of alkyl halides is not correct?

S_N1 reactions usually proceed with

Show the best way to prepare CH₃OCH(CH₃)₂ by an S_N2 reaction.

Which of the following iodides undergoes S_N1 solvolysis in water the fastest?

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

Identify the alkyl halide that reacts the fastest in an S_N1 reaction.

What product results from the S_N2 reaction between (R)-2-chloropentane and hydroxide?

Which of the following S_N2 reactions is the fastest?