Question 1

Write a detailed, stepwise mechanism for the following reaction.

Accepted Answer

The answer of Write a detailed, stepwise mechanism for the...

Question 2

Would chlorination or bromination of 2,5-dimethylhexane produce a greater yield of 1-halo-2,5-dimethylhexane?

Accepted Answer

The answer of Would chlorination or bromination of 2,5-dimethylhexane produce...

Question 3

What sequence of reagents can be used to convert 3,3-dimethylpentane into 3,3-dimethyl-2-pentanone?

Accepted Answer

1. Br₂, hν

Question 4

Consider the reaction: CH3CH2 ∙ + Br2 → CH3CH2Br + Br ∙. Given that this reaction has an activation energy of +6 kcal/mol and a ΔH° of -22 kcal/mol, sketch a reaction-energy profile for this reaction. Label the axes and show Ea and ΔH° on your drawing.

Accepted Answer

Question 5

Calculate the percentage of 2-chloro-2-methyl butane in the following reaction.

Accepted Answer

A) 11.56% 
B) 27.77% 
C) 23.14% 
D) 35.18% 
E) 13.88% 
A) 11.56% 
B) 27.77% 
C) 23.14% 
D) 35.18% 
E) 13.88%

Question 6

Which of the following is not an intermediate or product in the reaction of

Accepted Answer

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

Question 7

How many distinct dichlorination products can result when isobutane is subjected to free radical chlorination?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 6 
A) 1 
B) 2 
C) 3 
D) 4 
E) 6

Question 8

How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl2?

Accepted Answer

A) 2 
B) 4 
C) 5 
D) 6 
E) 8 
A) 2 
B) 4 
C) 5 
D) 6 
E) 8

Question 9

Given the bond dissociation energies below (in kcal/mol), estimate the ΔH° for the propagation step   CH3CH2CH2-H 98 (CH3)2CH-H 95
Cl-Cl 58
H-Cl 103
CH3CH2CH2-Cl 81
(CH3)2CH-Cl 80

Accepted Answer

A) -22 kcal/mol 
B) +22 kcal/mol 
C) -40 kcal/mol 
D) +45 kcal/mol 
E) -45 kcal/mol 
A) -22 kcal/mol 
B) +22 kcal/mol 
C) -40 kcal/mol 
D) +45 kcal/mol 
E) -45 kcal/mol

Question 10

The following molecule contains how many 1°, 2°, and 3° hydrogens?

Accepted Answer

The answer of The following molecule contains how many 1°,...

Question 11

Identify the most stable radical.

Accepted Answer

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

Question 12

Which of the following is a step in the mechanism of the reaction shown?

Accepted Answer

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

Question 13

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 14

How many monochlorinated products would be obtained from 2-methylbutane? Show the structures and give their IUPAC names.

Accepted Answer

The answer of How many monochlorinated products would be obtained...

Question 15

What reagent can best be used to convert cyclopentene to 3-bromocyclopentene in a single step?

Accepted Answer

A) Br2, hυ 
B) NBS, Δ 
C) HBr 
D) HBr with peroxide 
E) none of the above 
A) Br2, hυ 
B) NBS, Δ 
C) HBr 
D) HBr with peroxide 
E) none of the above

Question 16

Calculate the percentage of 2-chloro-3,4-dimethylheptane formed in the following reaction.

Accepted Answer

A) 6)70 
B) 11.16 
C) 16.96 
D) 22.32 
E) 26.80 
A) 6)70 
B) 11.16 
C) 16.96 
D) 22.32 
E) 26.80

Question 17

Given the bond dissociation energies below (in kcal/mol), calculate the overall ΔH° for the following reaction:
(CH3)3CH + Br2 → (CH3)3CBr + HBr
(CH3)3C-H 91
(CH3)3C-Br 65
Br-Br 46
H-Br 88
CH3-Br 70

Accepted Answer

Question 18

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

Accepted Answer

1. Br₂, hυ

Question 19

How many distinct alkyl chlorides can be obtained from monochlorination of 2,3-dimethylpentane?

Accepted Answer

A) 5 
B) 8 
C) 10 
D) 12 
E) 16 
A) 5 
B) 8 
C) 10 
D) 12 
E) 16

Question 20

Give the best product for the reaction.

Accepted Answer

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

Exam 13: Reactions of Alkanes, Radicals

Write a detailed, stepwise mechanism for the following reaction.

Would chlorination or bromination of 2,5-dimethylhexane produce a greater yield of 1-halo-2,5-dimethylhexane?

What sequence of reagents can be used to convert 3,3-dimethylpentane into 3,3-dimethyl-2-pentanone?

Consider the reaction: CH3CH2 ∙ + Br2 → CH3CH2Br + Br ∙. Given that this reaction has an activation energy of +6 kcal/mol and a ΔH° of -22 kcal/mol, sketch a reaction-energy profile for this reaction. Label the axes and show Ea and ΔH° on your drawing.

Calculate the percentage of 2-chloro-2-methyl butane in the following reaction.

Which of the following is not an intermediate or product in the reaction of

How many distinct dichlorination products can result when isobutane is subjected to free radical chlorination?

How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl2?

Given the bond dissociation energies below (in kcal/mol), estimate the ΔH° for the propagation step CH3CH2CH2-H 98 (CH3)2CH-H 95 Cl-Cl 58 H-Cl 103 CH3CH2CH2-Cl 81 (CH3)2CH-Cl 80

The following molecule contains how many 1°, 2°, and 3° hydrogens?

Identify the most stable radical.

Which of the following is a step in the mechanism of the reaction shown?

Provide the major organic product of the following reaction.

How many monochlorinated products would be obtained from 2-methylbutane? Show the structures and give their IUPAC names.

What reagent can best be used to convert cyclopentene to 3-bromocyclopentene in a single step?

Calculate the percentage of 2-chloro-3,4-dimethylheptane formed in the following reaction.

Given the bond dissociation energies below (in kcal/mol), calculate the overall ΔH° for the following reaction: (CH3)3CH + Br2 → (CH3)3CBr + HBr (CH3)3C-H 91 (CH3)3C-Br 65 Br-Br 46 H-Br 88 CH3-Br 70

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

How many distinct alkyl chlorides can be obtained from monochlorination of 2,3-dimethylpentane?

Give the best product for the 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

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

Consider the reaction: CH₃CH₂∙ + Br₂ → CH₃CH₂Br + Br ∙. Given that this reaction has an activation energy of +6 kcal/mol and a ΔH° of -22 kcal/mol, sketch a reaction-energy profile for this reaction. Label the axes and show E_a and ΔH° on your drawing.

How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl₂?

Given the bond dissociation energies below (in kcal/mol), estimate the ΔH° for the propagation step CH₃CH₂CH₂-H 98 (CH₃)₂CH-H 95 Cl-Cl 58 H-Cl 103 CH₃CH₂CH₂-Cl 81 (CH₃)₂CH-Cl 80

Given the bond dissociation energies below (in kcal/mol), calculate the overall ΔH° for the following reaction: (CH₃)₃CH + Br₂ → (CH₃)₃CBr + HBr (CH₃)₃C-H 91 (CH₃)₃C-Br 65 Br-Br 46 H-Br 88 CH₃-Br 70