Question 1

Calculate the percentage of 1-chloro-3-methylbutane 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 2

When butane undergoes free radical bromination, the product mixture contains 98% 2-bromobutane and 2% 1-bromobutane. How many times more susceptible to hydrogen atom abstraction is a secondary hydrogen in butane than is a primary hydrogen?

Accepted Answer

A) 100 
B) 73.5 
C) 50 
D) 8)7 
E) 1)5 
A) 100 
B) 73.5 
C) 50 
D) 8)7 
E) 1)5

Question 3

List the following radicals in order of increasing stability (ie, from least stable to most stable).
(CH3)3C ∙, CH2
    CHCH2 ∙, CH3CH2 ∙, CH3 ∙, (CH3)2CH ∙

Accepted Answer

CH₃ ∙ < CH₃CH₂∙ < (CH₃)₂C

Question 4

Give the best product(s)for the reaction.

Accepted Answer

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

Question 5

Which of the following is the best description of propane, CH3CH2CH3, at room temperature?

Accepted Answer

A) liquid, soluble in H2O 
B) gas, soluble in gasoline 
C) liquid, soluble in gasoline 
D) gas, soluble in water 
E) solid, soluble in gasoline 
A) liquid, soluble in H2O 
B) gas, soluble in gasoline 
C) liquid, soluble in gasoline 
D) gas, soluble in water 
E) solid, soluble in gasoline

Question 6

A hydrocarbon with molecular formula C5H12 is subjected to free radical chlorination conditions and only one monochlorinated product resulted. Provide the structure of this product.

Accepted Answer

Question 7

Provide the major organic product of the following reactions.

Accepted Answer

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

Question 8

Calculate the percentage of 3-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 9

During the free radical chlorination of methane, which of the following reactions has the lowest collision frequency?

Accepted Answer

A) Cl ∙ + ∙ CH3 → CH3Cl 
B) Cl ∙ + Cl2 → Cl2 + Cl ∙ 
C) ∙ CH3 + CH4 → CH4 + ∙ CH3 
D) ∙ CH3 + Cl2 → CH3Cl + Cl ∙ 
A) Cl ∙ + ∙ CH3 → CH3Cl 
B) Cl ∙ + Cl2 → Cl2 + Cl ∙ 
C) ∙ CH3 + CH4 → CH4 + ∙ CH3 
D) ∙ CH3 + Cl2 → CH3Cl + Cl ∙

Question 10

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 11

Devise methods by which (CH3)2C   CH2 could be synthesized from 2-methylpropane.

Accepted Answer

Br₂, hυ; Na

Question 12

Give the best product for the reaction.

Accepted Answer

A)    
B)    
C)    
D) BrCH2CH2CH3 
E) BrCH2CH2CH2Br 
A)    
B)    
C)    
D) BrCH2CH2CH3 
E) BrCH2CH2CH2Br

Question 13

What role do vitamins C and E play in biological radical reactions?

Accepted Answer

Unwanted radicals in biological systems

Question 14

If cyclohexane reacts with excess Cl2 at high temperature, how many distinct dichlorocyclohexane products are possible? Include all stereoisomers.

Accepted Answer

A) 5 
B) 6 
C) 7 
D) 8 
E) 9 
A) 5 
B) 6 
C) 7 
D) 8 
E) 9

Question 15

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

Accepted Answer

1. HBr, pe

Question 16

Which of the following is the rate-determining step for the monobromination of cyclohexane?

Accepted Answer

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

Question 17

A sample of (R)-2-chlorobutane,   reacts with Br2 in the presence of light, and all the products having the formula C4H8BrCl were isolated. Two possible isomers are shown below:   Of these:

Accepted Answer

A) only I was formed. 
B) both I and II were formed in equal amounts. 
C) both I and II were formed in unequal amounts. 
D) only II was formed. 
E) neither I nor II was formed. 
A) only I was formed. 
B) both I and II were formed in equal amounts. 
C) both I and II were formed in unequal amounts. 
D) only II was formed. 
E) neither I nor II was formed.

Question 18

What C5H12 isomer will give only a single monochlorination product?

Accepted Answer

(CH₃)₄C or n

Question 19

Consider the bond dissociation energies listed below in kcal/mol. CH3-Br 70
CH3CH2-Br 68
(CH3)2CH-Br 68
(CH3)3C-Br 65
These data show that the carbon-bromine bond is weakest when bromine is bound to a ________.

Accepted Answer

A) methyl carbon 
B) primary carbon 
C) secondary carbon 
D) tertiary carbon 
E) quaternary carbon 
A) methyl carbon 
B) primary carbon 
C) secondary carbon 
D) tertiary carbon 
E) quaternary carbon

Question 20

Which H in the molecule below is removed to generate the most stable carbon radical? Show the structure of this radical.

Accepted Answer

The answer of Which H in the molecule below is...

Exam 13: Reactions of Alkanes, Radicals

Calculate the percentage of 1-chloro-3-methylbutane in the following reaction.

When butane undergoes free radical bromination, the product mixture contains 98% 2-bromobutane and 2% 1-bromobutane. How many times more susceptible to hydrogen atom abstraction is a secondary hydrogen in butane than is a primary hydrogen?

List the following radicals in order of increasing stability (ie, from least stable to most stable). (CH3)3C ∙, CH2 CHCH2 ∙, CH3CH2 ∙, CH3 ∙, (CH3)2CH ∙

Give the best product(s)for the reaction.

Which of the following is the best description of propane, CH3CH2CH3, at room temperature?

A hydrocarbon with molecular formula C5H12 is subjected to free radical chlorination conditions and only one monochlorinated product resulted. Provide the structure of this product.

Provide the major organic product of the following reactions.

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

During the free radical chlorination of methane, which of the following reactions has the lowest collision frequency?

What is the major product of the following reaction?

Devise methods by which (CH3)2C CH2 could be synthesized from 2-methylpropane.

Give the best product for the reaction.

What role do vitamins C and E play in biological radical reactions?

If cyclohexane reacts with excess Cl2 at high temperature, how many distinct dichlorocyclohexane products are possible? Include all stereoisomers.

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

Which of the following is the rate-determining step for the monobromination of cyclohexane?

A sample of (R)-2-chlorobutane, reacts with Br2 in the presence of light, and all the products having the formula C4H8BrCl were isolated. Two possible isomers are shown below: Of these:

What C5H12 isomer will give only a single monochlorination product?

Consider the bond dissociation energies listed below in kcal/mol. CH3-Br 70 CH3CH2-Br 68 (CH3)2CH-Br 68 (CH3)3C-Br 65 These data show that the carbon-bromine bond is weakest when bromine is bound to a ________.

Which H in the molecule below is removed to generate the most stable carbon radical? Show the structure of this radical.

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

List the following radicals in order of increasing stability (ie, from least stable to most stable). (CH₃)₃C ∙, CH₂ CHCH₂ ∙, CH₃CH₂ ∙, CH₃ ∙, (CH₃)₂CH ∙

Which of the following is the best description of propane, CH₃CH₂CH₃, at room temperature?

A hydrocarbon with molecular formula C₅H₁₂ is subjected to free radical chlorination conditions and only one monochlorinated product resulted. Provide the structure of this product.

Devise methods by which (CH₃)₂C CH₂ could be synthesized from 2-methylpropane.

If cyclohexane reacts with excess Cl₂ at high temperature, how many distinct dichlorocyclohexane products are possible? Include all stereoisomers.

A sample of (R)-2-chlorobutane, reacts with Br₂ in the presence of light, and all the products having the formula C₄H₈BrCl were isolated. Two possible isomers are shown below: Of these:

What C₅H₁₂ isomer will give only a single monochlorination product?

Consider the bond dissociation energies listed below in kcal/mol. CH₃-Br 70 CH₃CH₂-Br 68 (CH₃)₂CH-Br 68 (CH₃)₃C-Br 65 These data show that the carbon-bromine bond is weakest when bromine is bound to a ________.