Question 1

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 2

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

Accepted Answer

1. Br₂, hυ

Question 3

Give the structure of the free radical intermediate for each product in a previous problem.

Accepted Answer

The answer of Give the structure of the free radical...

Question 4

Calculate the theoretical percent yields of the four monochlorinated products that result when 2-methylbutane is subjected to free radical chlorination. Assume that the relative ease of hydrogen abstraction in the chlorination process is 5 for 3°; 3.8 for 2°; and 1 for 1° hydrogens.

Accepted Answer

2-chloro-2-methylbutane
1 x 5 = 5; %yiel

Question 5

Give the steps and intermediates needed for the following reaction.

Accepted Answer

The answer of Give the steps and intermediates needed for...

Question 6

Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.

Accepted Answer

The reaction proceeds via the addition o

Question 7

Identify the hydrogen that will react the fastest in a radical halogenation reaction.

Accepted Answer

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

Question 8

Devise methods by which the following molecule could be synthesized from cyclohexane.

Accepted Answer

Cl₂, hυ; Na

Question 9

Provide the structure of semiquinone radical.

Accepted Answer

The answer of Provide the structure of semiquinone radical....

Question 10

Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-1-heptene.

Accepted Answer

1. Br₂, hυ

Question 11

Which of the following most nearly describes the geometry of the methyl radical?

Accepted Answer

A) trigonal pyramid, bond angle 109.5° 
B) trigonal pyramid, bond angle 120° 
C) trigonal planar, bond angle 109.5° 
D) trigonal planar, bond angle 120° 
A) trigonal pyramid, bond angle 109.5° 
B) trigonal pyramid, bond angle 120° 
C) trigonal planar, bond angle 109.5° 
D) trigonal planar, bond angle 120°

Question 12

Which of the following compounds is more stable? Explain.

Accepted Answer

(a)is more stable than (b). Al

Question 13

Provide the major organic product of the reaction below.

Accepted Answer

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

Question 14

Which of the following is the best synthesis of 1, 1-dibromopropane?

Accepted Answer

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

Question 15

In the free radical chlorination of ethane, the step in which the Cl radical abstracts a H atom from ethane is ________ and the transition state most closely resembles ________.

Accepted Answer

A) exothermic, the reactants 
B) endothermic, the reactants 
C) exothermic, the products 
D) endothermic, the products 
E) endothermic, a carbocation 
A) exothermic, the reactants 
B) endothermic, the reactants 
C) exothermic, the products 
D) endothermic, the products 
E) endothermic, a carbocation

Question 16

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 17

Use the Hammond Postulate to explain why free radical brominations are more selective than free radical chlorinations.

Accepted Answer

The first propagation step in free radic

Question 18

Which of the halogens below undergoes free radical halogenation with ethane most rapidly?

Accepted Answer

A) fluorine 
B) chlorine 
C) iodine 
D) bromine 
E) pyridine 
A) fluorine 
B) chlorine 
C) iodine 
D) bromine 
E) pyridine

Question 19

What sequence of reagents can be used to accomplish the conversion shown below?

Accepted Answer

1. Br₂, hν

Question 20

Write the structures of all of the monobromination products of 1,1,3,3-tetramethylcyclobutane.

Accepted Answer

The answer of Write the structures of all of the...

Exam 13: Reactions of Alkanes, Radicals

What is the major product of the following reaction?

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

Give the structure of the free radical intermediate for each product in a previous problem.

Calculate the theoretical percent yields of the four monochlorinated products that result when 2-methylbutane is subjected to free radical chlorination. Assume that the relative ease of hydrogen abstraction in the chlorination process is 5 for 3°; 3.8 for 2°; and 1 for 1° hydrogens.

Give the steps and intermediates needed for the following reaction.

Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.

Identify the hydrogen that will react the fastest in a radical halogenation reaction.

Devise methods by which the following molecule could be synthesized from cyclohexane.

Provide the structure of semiquinone radical.

Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-1-heptene.

Which of the following most nearly describes the geometry of the methyl radical?

Which of the following compounds is more stable? Explain.

Provide the major organic product of the reaction below.

Which of the following is the best synthesis of 1, 1-dibromopropane?

In the free radical chlorination of ethane, the step in which the Cl radical abstracts a H atom from ethane is ________ and the transition state most closely resembles ________.

Provide the major organic product of the reaction shown below.

Use the Hammond Postulate to explain why free radical brominations are more selective than free radical chlorinations.

Which of the halogens below undergoes free radical halogenation with ethane most rapidly?

What sequence of reagents can be used to accomplish the conversion shown below?

Write the structures of all of the monobromination products of 1,1,3,3-tetramethylcyclobutane.

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

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

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

In the free radical chlorination of ethane, the step in which the Cl radical abstracts a H atom from ethane is and the transition state most closely resembles .