Question 1

Briefly explain why when cyclopentene is treated with Br₂ that trans-1,2-dibromocyclopentane is the major product at high temperatures but at low temperatures,racemic 3-bromocyclopentene is the major product.

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Question 2

Draw bond-line formulas of all dichloro derivatives that might be formed when 1-chloro-2,2,3,3-tetramethylpentane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

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Question 3

Deduce the structure of a substance,C₈H₁₈,which gives only a single monochloro derivative upon reaction with Cl₂ under UV irradiation.

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Question 4

Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.

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Question 5

A covalent bond breaking so that each of the resulting intermediates bears a single unpaired electron is an example of ___ bond cleavage.

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Question 6

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.

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Question 7

Provide a reasonable mechanistic explanation for the formation of small amounts of 3,3,4,4-tetramethylhexane during the free-radical bromination of 2-methylbutane.

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Question 8

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

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Question 9

In a chain-propagating step,one radical ___.

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Question 10

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,2,4-trimethylpentane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

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Question 11

Briefly,but clearly,explain the following observation: When 2-methylbutane reacts with Cl₂/h$v$,the monochlorinated products consist of four constitutional isomers in significant yields.However,when the same alkane is allowed to react with Br₂/ h$v$,there is only one major monobromination product.

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When 2-methylbutane reacts...

Question 12

Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.

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Question 13

While the electrophilic addition of HBr to an alkene is ionic and follows Markovnikov's rule,if the reaction is done in the presence of peroxides it becomes a ___ reaction and is ___ in regiochemistry.

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Question 14

The reason why ___ and ___ radicals are more stable than alkyl radicals is due to electron delocalization through resonance.

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Question 15

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,3-dimethylbutane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

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Question 16

In a chain-initiating step,radicals are ___.

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Question 17

Although alkyl radicals are uncharged,the carbon bearing the odd electron is electron ___,and alkyl groups provide a ___ effect.

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Question 18

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.

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Question 19

In a chain-terminating step,radicals are ___.

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Question 20

Determine the identification of compounds W,X,Y and Z using the structural information shown below.

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Quiz 10: Radical Reactions

Briefly explain why when cyclopentene is treated with Br₂ that trans-1,2-dibromocyclopentane is the major product at high temperatures but at low temperatures,racemic 3-bromocyclopentene is the major product.

Draw bond-line formulas of all dichloro derivatives that might be formed when 1-chloro-2,2,3,3-tetramethylpentane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Deduce the structure of a substance,C₈H₁₈,which gives only a single monochloro derivative upon reaction with Cl₂ under UV irradiation.

Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.

A covalent bond breaking so that each of the resulting intermediates bears a single unpaired electron is an example of ___ bond cleavage.

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.

Provide a reasonable mechanistic explanation for the formation of small amounts of 3,3,4,4-tetramethylhexane during the free-radical bromination of 2-methylbutane.

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

In a chain-propagating step,one radical ___.

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,2,4-trimethylpentane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.

While the electrophilic addition of HBr to an alkene is ionic and follows Markovnikov's rule,if the reaction is done in the presence of peroxides it becomes a _ reaction and is _ in regiochemistry.

The reason why _ and _ radicals are more stable than alkyl radicals is due to electron delocalization through resonance.

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,3-dimethylbutane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

In a chain-initiating step,radicals are ___.

Although alkyl radicals are uncharged,the carbon bearing the odd electron is electron _,and alkyl groups provide a _ effect.

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.

In a chain-terminating step,radicals are ___.

Determine the identification of compounds W,X,Y and Z using the structural information shown below.

Quiz 10: Radical Reactions

Briefly explain why when cyclopentene is treated with Br2 that trans-1,2-dibromocyclopentane is the major product at high temperatures but at low temperatures,racemic 3-bromocyclopentene is the major product.

Draw bond-line formulas of all dichloro derivatives that might be formed when 1-chloro-2,2,3,3-tetramethylpentane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Deduce the structure of a substance,C8H18,which gives only a single monochloro derivative upon reaction with Cl2 under UV irradiation.

Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.

A covalent bond breaking so that each of the resulting intermediates bears a single unpaired electron is an example of ___ bond cleavage.

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.

Provide a reasonable mechanistic explanation for the formation of small amounts of 3,3,4,4-tetramethylhexane during the free-radical bromination of 2-methylbutane.

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

In a chain-propagating step,one radical ___.

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,2,4-trimethylpentane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.

While the electrophilic addition of HBr to an alkene is ionic and follows Markovnikov's rule,if the reaction is done in the presence of peroxides it becomes a ___ reaction and is ___ in regiochemistry.

The reason why ___ and ___ radicals are more stable than alkyl radicals is due to electron delocalization through resonance.

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,3-dimethylbutane is allowed to react with Cl2 under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

In a chain-initiating step,radicals are ___.

Although alkyl radicals are uncharged,the carbon bearing the odd electron is electron ___,and alkyl groups provide a ___ effect.

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.

In a chain-terminating step,radicals are ___.

Determine the identification of compounds W,X,Y and Z using the structural information shown below.

Briefly explain why when cyclopentene is treated with Br₂ that trans-1,2-dibromocyclopentane is the major product at high temperatures but at low temperatures,racemic 3-bromocyclopentene is the major product.

Draw bond-line formulas of all dichloro derivatives that might be formed when 1-chloro-2,2,3,3-tetramethylpentane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Deduce the structure of a substance,C₈H₁₈,which gives only a single monochloro derivative upon reaction with Cl₂ under UV irradiation.

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.

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,2,4-trimethylpentane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

While the electrophilic addition of HBr to an alkene is ionic and follows Markovnikov's rule,if the reaction is done in the presence of peroxides it becomes a _ reaction and is _ in regiochemistry.

The reason why _ and _ radicals are more stable than alkyl radicals is due to electron delocalization through resonance.

Draw bond-line formulas of all monochloro derivatives that might be formed when 2,3-dimethylbutane is allowed to react with Cl₂ under UV irradiation.For each structure,indicate,with an asterisk,any stereocenters that might be present.

Although alkyl radicals are uncharged,the carbon bearing the odd electron is electron _,and alkyl groups provide a _ effect.

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.