Question 1

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 2

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 3

How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 5 
A) 1 
B) 2 
C) 3 
D) 4 
E) 5

Question 4

Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

Accepted Answer

A) SN2 and SN1 
B) E1 and E2 
C) SN2 and E2 
D) E1 and SN1 
E) E2 and SN1 
A) SN2 and SN1 
B) E1 and E2 
C) SN2 and E2 
D) E1 and SN1 
E) E2 and SN1

Question 5

Can primary alkyl halides react by SN2, SN1, E2, and E1 mechanisms? Are any of these mechanisms prohibited? What conditions favor a particular mechanism?

Accepted Answer

Only S_N2 and E2 pathways are available to

Question 6

Give the major product for the following E1 reaction.

Accepted Answer

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

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

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 9

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 10

Give the major product for the following E2 reaction.

Accepted Answer

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

Question 11

Give the mechanism of the reaction shown below.

Accepted Answer

The answer of Give the mechanism of the reaction shown...

Question 12

Starting with 2-butene, which of the following is the best method for preparing 2-butyne?

Accepted Answer

A) HBr; H2/Ni; Zn/H+ 
B) HBr; Zn/H+; H2/Ni 
C) Br2/CCl4; Zn/H+; H2/Ni 
D) Br2/CCl4; 2NaNH2 
E) HBr; NaNH2 
A) HBr; H2/Ni; Zn/H+ 
B) HBr; Zn/H+; H2/Ni 
C) Br2/CCl4; Zn/H+; H2/Ni 
D) Br2/CCl4; 2NaNH2 
E) HBr; NaNH2

Question 13

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

Accepted Answer

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

Question 14

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 15

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 16

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 17

Give the product from the reaction of 1-pentene with the following reagents.
1. Cl2
2. -OH
3. NaNH2
4. CH3CH2Br

Accepted Answer

Question 18

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 19

Draw the alkene product which results when 1-bromopentane is heated in acetone containing NaOH. Give a detailed, step-by-step mechanism for the production of this compound.

Accepted Answer

The answer of Draw the alkene product which results when...

Question 20

Give the major product for the following E2 reaction.

Accepted Answer

A)    
B)    
C)    
D)    
E) no reaction 
A)    
B)    
C)    
D)    
E) no reaction

Exam 10: Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Provide the major organic product of the following reaction.

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

How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?

Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

Can primary alkyl halides react by SN2, SN1, E2, and E1 mechanisms? Are any of these mechanisms prohibited? What conditions favor a particular mechanism?

Give the major product for the following E1 reaction.

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

What mechanism predominates in the reaction below?

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

Give the major product for the following E2 reaction.

Give the mechanism of the reaction shown below.

Starting with 2-butene, which of the following is the best method for preparing 2-butyne?

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

Provide the major organic product of the following reaction.

Which alkyl halide reacts the fastest in an E2 reaction?

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

Give the product from the reaction of 1-pentene with the following reagents. 1. Cl2 2. -OH 3. NaNH2 4. CH3CH2Br

What is the major organic product of the following reaction?

Draw the alkene product which results when 1-bromopentane is heated in acetone containing NaOH. Give a detailed, step-by-step mechanism for the production of this compound.

Give the major product for the following E2 reaction.

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

Substitution Reactions of Alkyl Halides

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

Can primary alkyl halides react by S_N2, S_N1, E2, and E1 mechanisms? Are any of these mechanisms prohibited? What conditions favor a particular mechanism?

Give the product from the reaction of 1-pentene with the following reagents. 1. Cl₂ 2. ^-OH 3. NaNH₂ 4. CH₃CH₂Br