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 elimination product which results when the alkyl bromide below is heated in ethanol.

Accepted Answer

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

Question 3

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

Accepted Answer

Primary halides cannot undergo

Question 4

Which of the compounds shown below is/are the product(s)of this reaction?

Accepted Answer

A) I only 
B) II only 
C) I and II are of equal yield. 
D) I is major, II is minor. 
E) I is minor, II is major. 
A) I only 
B) II only 
C) I and II are of equal yield. 
D) I is major, II is minor. 
E) I is minor, II is major.

Question 5

When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3, the more highly substituted alkene product predominates. When KOC(CH3)3 is used instead, the less highly substituted alkene product predominates. Offer an explanation.

Accepted Answer

The unhindered ethoxide produces the mor

Question 6

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 7

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?

Accepted Answer

A) 1-chloropentane 
B) 2-chloropentane 
C) 3-chloropentane 
D) 1-chloro-2-methylbutane 
E) 1-chloro-3-methylbutane 
A) 1-chloropentane 
B) 2-chloropentane 
C) 3-chloropentane 
D) 1-chloro-2-methylbutane 
E) 1-chloro-3-methylbutane

Question 8

Give the mechanism of the reaction shown below.

Accepted Answer

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

Question 9

Which of the following correctly reflects relative stabilities of carbocations?

Accepted Answer

A) 3° allylic > 2° > 1° benzylic 
B) methyl > 2° benzylic > 3° 
C) 3° benzylic > vinyl > 1° 
D) 2° allylic > 2° > vinyl 
E) 1° benzylic > 3° > 3° allylic 
A) 3° allylic > 2° > 1° benzylic 
B) methyl > 2° benzylic > 3° 
C) 3° benzylic > vinyl > 1° 
D) 2° allylic > 2° > vinyl 
E) 1° benzylic > 3° > 3° allylic

Question 10

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 11

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 12

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...

Question 13

Give the mechanism of the reaction shown below.

Accepted Answer

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

Question 14

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)

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 elimination product which results when the alkyl bromide below is heated in ethanol.

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

Which of the compounds shown below is/are the product(s)of this reaction?

When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3, the more highly substituted alkene product predominates. When KOC(CH3)3 is used instead, the less highly substituted alkene product predominates. Offer an explanation.

What mechanism predominates in the reaction below?

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?

Give the mechanism of the reaction shown below.

Which of the following correctly reflects relative stabilities of carbocations?

What is the major organic product of the following reaction?

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

Give the mechanism of the reaction shown below.

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

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

When 1-iodo-1-methylcyclohexane is treated with NaOCH₂CH₃, the more highly substituted alkene product predominates. When KOC(CH₃)₃ is used instead, the less highly substituted alkene product predominates. Offer an explanation.