Question 1

Which of the following SN2 reactions is the slowest?

Accepted Answer

A) CH3CH2CHBrCH3 + OH- → CH3CH2CHOHCH3 + Br- 
B) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr 
C) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br- 
D) CH3CH2CH2CH2Br + H2O → CH3CH2CH2CH2OH + HBr 
A) CH3CH2CHBrCH3 + OH- → CH3CH2CHOHCH3 + Br- 
B) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr 
C) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br- 
D) CH3CH2CH2CH2Br + H2O → CH3CH2CH2CH2OH + HBr

Question 2

What is the leaving group in the reaction shown below?

Accepted Answer

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

Question 3

Which of the following alkyl halides gives the fastest SN1 reaction?

Accepted Answer

A) CH3CH2CH2Br 
B)    
C)    
D) CH3CH2CH2I 
E) CH3CH2CH2Cl 
A) CH3CH2CH2Br 
B)    
C)    
D) CH3CH2CH2I 
E) CH3CH2CH2Cl

Question 4

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 5

Which alkyl halide reacts the fastest in an E2 reaction?

Accepted Answer

A) 2-chloro-2-methylbutane 
B) 1-chlorobutane 
C) 1-chloro-2-methylbutane 
D) 2-chlorobutane 
E) chloromethane 
A) 2-chloro-2-methylbutane 
B) 1-chlorobutane 
C) 1-chloro-2-methylbutane 
D) 2-chlorobutane 
E) chloromethane

Question 6

What would be the product of this reaction? Also,provide the name of the mechanism (SN2,SN1,E2 or E1).

Accepted Answer

No reaction.It should undergo

Question 7

Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

Accepted Answer

A) (R)-2-bromo-3-ethylpentane 
B) (S)-2-bromo-3-ethylpentane 
C) (R)-3-bromo-2-methylpentane 
D) (S)-3-bromo-2-methylpentane 
E) 3-bromo-3-ethylpentane 
A) (R)-2-bromo-3-ethylpentane 
B) (S)-2-bromo-3-ethylpentane 
C) (R)-3-bromo-2-methylpentane 
D) (S)-3-bromo-2-methylpentane 
E) 3-bromo-3-ethylpentane

Question 8

Identify the halide(s)that react in a SN1 reaction.You may choose more than one answer.

Accepted Answer

A) benzyl bromide 
B) bromobenzene 
C) 1-bromo-1-butene 
D) 1-bromo-2-butene 
E) 2-bromo-2-phenylpropane 
A) benzyl bromide 
B) bromobenzene 
C) 1-bromo-1-butene 
D) 1-bromo-2-butene 
E) 2-bromo-2-phenylpropane

Question 9

Which of the following is the best nucleophile in water?

Accepted Answer

A) I- 
B) CH3SCH3 
C) CH3OCH3 
D) Cl- 
A) I- 
B) CH3SCH3 
C) CH3OCH3 
D) Cl-

Question 10

Which halide reacts most rapidly via an SN2 mechanism?

Accepted Answer

A) (CH3)CCH2CH2F 
B) (CH3)CCH2CH2Cl 
C) (CH3)CCH2CH2Br 
D) (CH3)CCH2CH2I 
E) All primary halides react at the same rate in SN2. 
A) (CH3)CCH2CH2F 
B) (CH3)CCH2CH2Cl 
C) (CH3)CCH2CH2Br 
D) (CH3)CCH2CH2I 
E) All primary halides react at the same rate in SN2.

Question 11

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

Accepted Answer

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

Question 12

Which of the following is not true for a SN1 mechanism?

Accepted Answer

A) The rate is dependent on the nucleophile. 
B) The rate is fastest in highly polar solvents. 
C) proceeds with a carbocation intermediate 
D) is a two step reaction 
E) Methyl iodide will not undergo this reaction. 
A) The rate is dependent on the nucleophile. 
B) The rate is fastest in highly polar solvents. 
C) proceeds with a carbocation intermediate 
D) is a two step reaction 
E) Methyl iodide will not undergo this reaction.

Question 13

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

Accepted Answer

CH₃Br < CH₃C

Question 14

Identify the alkyl halide that reacts the fastest in a E1 reaction.

Accepted Answer

A)    
B) CH2     CHCl 
C)    
D)    
E) CH3CH2CH2Cl 
A)    
B) CH2     CHCl 
C)    
D)    
E) CH3CH2CH2Cl

Question 15

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 16

How would you obtain the following products from 1-bromo-1-methylcyclohexane?

Accepted Answer

1.(CH₃)₃COK

Question 17

What is the major product of the following reaction?

Accepted Answer

A) CH2     CHCH2CH3 
B) CH3CH   CHCH3 
C)    
D) CH3CH2CH2CH2OCH2CH3 
E)    
A) CH2     CHCH2CH3 
B) CH3CH   CHCH3 
C)    
D) CH3CH2CH2CH2OCH2CH3 
E)

Question 18

Which of the following compounds undergoes E2 reactions with the fastest rate?

Accepted Answer

A)    
B) CH3CH2CH2Cl 
C) CH3CH2CH2I 
D)    
E) CH3CH2CH2Br 
A)    
B) CH3CH2CH2Cl 
C) CH3CH2CH2I 
D)    
E) CH3CH2CH2Br

Question 19

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

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

Question 20

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Accepted Answer

The answer of Draw all likely alkene products in the...

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

Which of the following SN2 reactions is the slowest?

What is the leaving group in the reaction shown below?

Which of the following alkyl halides gives the fastest SN1 reaction?

Provide the major organic product of the following reaction.

Which alkyl halide reacts the fastest in an E2 reaction?

What would be the product of this reaction? Also,provide the name of the mechanism (SN2,SN1,E2 or E1).

Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

Identify the halide(s)that react in a SN1 reaction.You may choose more than one answer.

Which of the following is the best nucleophile in water?

Which halide reacts most rapidly via an SN2 mechanism?

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

Which of the following is not true for a SN1 mechanism?

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

Identify the alkyl halide that reacts the fastest in a E1 reaction.

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

How would you obtain the following products from 1-bromo-1-methylcyclohexane?

What is the major product of the following reaction?

Which of the following compounds undergoes E2 reactions with the fastest rate?

Provide the structure of the major organic product which results in the following reaction.

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

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 alkyl halides gives the fastest S_N1 reaction?

What would be the product of this reaction? Also,provide the name of the mechanism (S_N2,S_N1,E2 or E1).

Identify the halide(s)that react in a S_N1 reaction.You may choose more than one answer.

Which halide reacts most rapidly via an S_N2 mechanism?

Which of the following is not true for a S_N1 mechanism?

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