Question 1

The reaction of 1-butene with HBr in the presence of peroxides yields 1-bromobutane.The mechanism for the reaction involves:

Accepted Answer

A) attack on the alkene by a Br+ ion. 
B) attack on the alkene by a H+ ion. 
C) attack on the alkene by a bromine atom,Br·. 
D) attack on the alkene by a hydrogen atom,H·. 
E) isomerization of the 2-bromobutane produced initially. 
A) attack on the alkene by a Br+ ion. 
B) attack on the alkene by a H+ ion. 
C) attack on the alkene by a bromine atom,Br·. 
D) attack on the alkene by a hydrogen atom,H·. 
E) isomerization of the 2-bromobutane produced initially.

Question 2

The terms "chain reaction" refer to a process where a long sequence of various intermediates are generated to arrive at the formation of a single product.

Accepted Answer

A) True 
 B)False

Question 3

What is the total number of trichloropropanes which can be produced by free radical chlorination of propane? Include all stereoisomers.

Accepted Answer

A) 4 
B) 5 
C) 6 
D) 7 
E) 8 
A) 4 
B) 5 
C) 6 
D) 7 
E) 8

Question 4

Which of the following would be the major product in the following reaction sequence?

Accepted Answer

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

Question 5

Which of these molecules is not expected to arise as a product of the high temperature chlorination of methane?

Accepted Answer

A) CCl4 
B) HCCl3 
C) CH2Cl2 
D) CH3CH3 
E) CH2=CH2 
A) CCl4 
B) HCCl3 
C) CH2Cl2 
D) CH3CH3 
E) CH2=CH2

Question 6

In the presence of light at 25 °C,isobutane (1 mol)and bromine (1 mol)yield which monobromo product(s)?

Accepted Answer

A) 2-Methyl-1-bromopropane (almost exclusively) 
B) 2-Methyl-2-bromopropane (almost exclusively) 
C) A mixture of 50% (
A) and 50% (
B)  
D) A mixture of 90% (
A) and 10% (
B)  
E) Butyl bromide 
A) 2-Methyl-1-bromopropane (almost exclusively) 
B) 2-Methyl-2-bromopropane (almost exclusively) 
C) A mixture of 50% (
A) and 50% (
B)  
D) A mixture of 90% (
A) and 10% (
B)  
E) Butyl bromide

Question 7

What product would result from 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 8

If chlorocyclopentane were chlorinated to form all possible dichloro compounds and the product mixture subjected to precise fractional distillation,how many fractions would be obtained (ideally)?

Accepted Answer

A) 3 
B) 4 
C) 5 
D) 7 
E) 9 
A) 3 
B) 4 
C) 5 
D) 7 
E) 9

Question 9

Which statement best describes the reaction of bromine with isobutane?

Accepted Answer

A) Bromine radical selectively abstracts the tertiary hydrogen. 
B) The transition state of the rate determining step is product-like. 
C) The major product formed from this reaction is 1-bromo-2-methylpropane. 
D) Bromine radical selectively abstracts the tertiary hydrogen and the transition state of the rate determining step is product-like. 
E) Bromine radical selectively abstracts the tertiary hydrogen,the transition state of the rate determining step is product-like,and the major product formed from this reaction is 1-bromo-2-methylpropane. 
A) Bromine radical selectively abstracts the tertiary hydrogen. 
B) The transition state of the rate determining step is product-like. 
C) The major product formed from this reaction is 1-bromo-2-methylpropane. 
D) Bromine radical selectively abstracts the tertiary hydrogen and the transition state of the rate determining step is product-like. 
E) Bromine radical selectively abstracts the tertiary hydrogen,the transition state of the rate determining step is product-like,and the major product formed from this reaction is 1-bromo-2-methylpropane.

Question 10

In a chain-terminating step,radicals are ___.

Accepted Answer

The answer of In a chain-terminating step,radicals are ___....

Question 11

What is the product for the following three-step reaction sequence?

Accepted Answer

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

Question 12

Draw bond-line formulas of all monochloro derivatives that might be formed when 3-ethylhexane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Accepted Answer

Question 13

Mono-bromination of the following alkane,   ,(using Br2 with light)would give?

Accepted Answer

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

Question 14

The mechanism for a free-radical reaction consists of three types of steps.These are: ___.

Accepted Answer

initiation,propagati

Question 15

Radical chlorinations are for the most part not synthetically practical due to high reactivity of the chlorine radical.

Accepted Answer

A) True 
 B)False

Question 16

What feature would you expect to see in the 1H NMR spectrum of B after subjecting A to the following reaction?

Accepted Answer

A) There would be only 4 aromatic protons at low field. 
B) The signal for the protons on the benzylic carbon would be a doublet. 
C) The signal for the methyl protons would be a triplet. 
D) The signal for the methyl protons would be a doublet. 
E) The signal for the methyl protons would integrate for only 2 hydrogens. 
A) There would be only 4 aromatic protons at low field. 
B) The signal for the protons on the benzylic carbon would be a doublet. 
C) The signal for the methyl protons would be a triplet. 
D) The signal for the methyl protons would be a doublet. 
E) The signal for the methyl protons would integrate for only 2 hydrogens.

Question 17

What would be the major product of the following reaction sequence?

Accepted Answer

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

Question 18

What is the final product,C,obtained via the following reaction sequence?

Accepted Answer

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

Question 19

Draw bond-line formulas of all monochloro derivatives that might be formed when 1,1-dimethylcyclobutane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Accepted Answer

Question 20

Mono-bromination of the following alkane,   ,(using Br2 with light)would give?

Accepted Answer

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

Exam 10: Radical Reactions

The reaction of 1-butene with HBr in the presence of peroxides yields 1-bromobutane.The mechanism for the reaction involves:

The terms "chain reaction" refer to a process where a long sequence of various intermediates are generated to arrive at the formation of a single product.

What is the total number of trichloropropanes which can be produced by free radical chlorination of propane? Include all stereoisomers.

Which of the following would be the major product in the following reaction sequence?

Which of these molecules is not expected to arise as a product of the high temperature chlorination of methane?

In the presence of light at 25 °C,isobutane (1 mol)and bromine (1 mol)yield which monobromo product(s)?

What product would result from the following reaction?

If chlorocyclopentane were chlorinated to form all possible dichloro compounds and the product mixture subjected to precise fractional distillation,how many fractions would be obtained (ideally)?

Which statement best describes the reaction of bromine with isobutane?

In a chain-terminating step,radicals are ___.

What is the product for the following three-step reaction sequence?

Draw bond-line formulas of all monochloro derivatives that might be formed when 3-ethylhexane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Mono-bromination of the following alkane, ,(using Br2 with light)would give?

The mechanism for a free-radical reaction consists of three types of steps.These are: ___.

Radical chlorinations are for the most part not synthetically practical due to high reactivity of the chlorine radical.

What feature would you expect to see in the 1H NMR spectrum of B after subjecting A to the following reaction?

What would be the major product of the following reaction sequence?

What is the final product,C,obtained via the following reaction sequence?

Draw bond-line formulas of all monochloro derivatives that might be formed when 1,1-dimethylcyclobutane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Mono-bromination of the following alkane, ,(using Br2 with light)would give?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Draw bond-line formulas of all monochloro derivatives that might be formed when 3-ethylhexane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Mono-bromination of the following alkane, ,(using Br₂ with light)would give?

What feature would you expect to see in the ¹H NMR spectrum of B after subjecting A to the following reaction?

Draw bond-line formulas of all monochloro derivatives that might be formed when 1,1-dimethylcyclobutane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Mono-bromination of the following alkane, ,(using Br₂ with light)would give?