Question 1

Identify the alkyl halide that reacts the fastest in an SN2 reaction.

Accepted Answer

A) 1-chloropropane 
B) 1-bromopropane 
C) 1-fluoropropane 
D) 1-iodopropane 
A) 1-chloropropane 
B) 1-bromopropane 
C) 1-fluoropropane 
D) 1-iodopropane

Question 2

Give the best answer for the reaction.

Accepted Answer

A) CH3CH2OCH3 
B) CH3CH2OCH2CH3 
C) CH3CH2OCH2CH2CH3 
D) CH3CH2CH2OCH2CH2CH3 
E) CH3CH2CH2OCH2CH2CH2CH3  
A) CH3CH2OCH3 
B) CH3CH2OCH2CH3 
C) CH3CH2OCH2CH2CH3 
D) CH3CH2CH2OCH2CH2CH3 
E) CH3CH2CH2OCH2CH2CH2CH3

Question 3

When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol,one of the products which results is shown below.Provide a detailed,stepwise mechanism for the production of this compound,and give the name of the mechanism by which it is produced.

Accepted Answer

The answer of When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol,one of...

Question 4

What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is treated with sodium methoxide in methanol?

Accepted Answer

The answer of What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is...

Question 5

Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?

Accepted Answer

Primary halides cannot undergo

Question 6

Give the mechanism including the transition state.

Accepted Answer

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

Question 7

Which of the following carbocations is the least stable?

Accepted Answer

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

Question 8

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 9

Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

Accepted Answer

A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. 
B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. 
C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density. 
D) tert-Butoxide is more nucleophilic because it is more basic. 
E) none of the above 
A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. 
B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. 
C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density. 
D) tert-Butoxide is more nucleophilic because it is more basic. 
E) none of the above

Question 10

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 11

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 12

Which of the following can't undergo nucleophilic substitution reactions?

Accepted Answer

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

Question 13

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Accepted Answer

No.All primary iodides are not

Question 14

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

Accepted Answer

The answer of How would you obtain the following product...

Question 15

What is/are the product(s)of the following reaction?

Accepted Answer

A)    
B) CH2     CH2 
C)    
D) A and B 
E) A and C 
A)    
B) CH2     CH2 
C)    
D) A and B 
E) A and C

Question 16

What mechanism predominates in the reaction below?

Accepted Answer

A) SN2 
B) SN1 without rearrangement 
C) SN1 with rearrangement 
D) E2 
E) E1 
A) SN2 
B) SN1 without rearrangement 
C) SN1 with rearrangement 
D) E2 
E) E1

Question 17

Give the major product for the following E1 reaction.

Accepted Answer

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

Question 18

Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane?

Accepted Answer

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

Question 19

What is the major product of the following reaction?

Accepted Answer

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

Question 20

Assuming no other changes,what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?

Accepted Answer

A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved 
A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

Identify the alkyl halide that reacts the fastest in an SN2 reaction.

Give the best answer for the reaction.

When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol,one of the products which results is shown below.Provide a detailed,stepwise mechanism for the production of this compound,and give the name of the mechanism by which it is produced.

What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is treated with sodium methoxide in methanol?

Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?

Give the mechanism including the transition state.

Which of the following carbocations is the least stable?

Which of the following solvents is aprotic?

Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

Provide the major organic product of the following reaction.

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

Which of the following can't undergo nucleophilic substitution reactions?

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

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

What is/are the product(s)of the following reaction?

What mechanism predominates in the reaction below?

Give the major product for the following E1 reaction.

Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane?

What is the major product of the following reaction?

Assuming no other changes,what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?

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

Identify the alkyl halide that reacts the fastest in an S_N2 reaction.

Do all primary alkyl iodides undergo S_N2 reactions with sodium cyanide in DMSO at identical rates? Explain.