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Organic Chemistry > Radical Reaction > Flashcards

Radical Reaction Flashcards

1
Q

Homolytic Bond Cleavage

A

Breaks a bond to form two radicals

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2
Q

What is the most stable radical?

A

Tertiary radical where methyl radical is the least stable

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3
Q

What is the common pattern for resonance of radicals?

A

An unpaired electron near a double bond

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4
Q

______________ radicals are more stable than tertiary radicals

A

Resonance Stablized

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5
Q

Radicals dont undergo ______________

A

Radical rearrangment

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6
Q

What are the different tpyes of arrow pushing for radicals?

A
  1. Homolytic Cleavage
  2. Addition to a double bond
  3. Hydrogen Abstraction
  4. Halogen Abstration
  5. Elimination
  6. Coupling
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7
Q

Homolytic Cleavage

A

Requires a large input of energy where the energy can either be heat or light (hv)

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8
Q

Addition to a double bond

A

A radical adds to a double bond thereby destroying the double & forming a single bond

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9
Q

Hydrogen addition

A

A radical can abstract a hydrogen atom from a compound generating a new radical

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10
Q

Halogen Abstraction

A

A radical can abstract a halogen atom generating a rew radical (similar to hydrogen abstraction)

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11
Q

Elimination

A

The position bearing the unparied electron is called the alpha position where in elimination the double bond forms between an alpha & beta position which results in a single bond at the beta position cleaved causing the compound to fragment into two pieces

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12
Q

Coupling

A

Two radicals join together & form a bond

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13
Q

Usually there are ___ or ___ arrows in a radical mechanism, where the number of arrows correspond to the number of electrons moving

A

2 or 3

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14
Q

What are the 3 phases in a radical reaction ?

A
  1. Initiation
  2. Termination
  3. Propagation
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15
Q

Initiation

A

When radicals are created

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16
Q

Terminiation

A

When two radicals cancel out each other by forming a bond

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17
Q

Propagation

A

The sum of the propagation step is the overall net reaction

18
Q

What is the mechanism for radical chlorination ?

A
  1. Homolytic cleavage (Inititation)
  2. Hydrogen abstraction (Propagation)
  3. Halogen abstraction (Propagation)
  4. Coupling (Termination)
19
Q

Radical initators

A

A compound with a weak bond that undergoes homolytic bond cleavage with ease

20
Q

___________ is often used as radical initators because the oxygen - oxygen bond is weak

A

Acyl Peroxides

21
Q

Radical Inhibitors

A

A compound that prevents a chain reaction from either getting started or continuing

22
Q

_____ & ____ are radical inhibitor

A

O2 & Hydroquinone

23
Q

Radical halogenation of ____ & ______ are only favorable

A

Br2 & Cl2 (Br2 is slower than Cl2 but Br2 is more selective than Cl2)

24
Q

Halogentation occurs at ____________ when using Br2 but doesn’t matter when using Cl2

A

More substitited Position

25
Q

When a reagent such as Br2 are least reactive they are usually the __________

A

Most selective

26
Q

What is the sterochemistry with halogenation of radicals?

A

The sterochemistry is unknown where there is a racemic mixture

27
Q

Allylic Bromination

A

When the Br is added to the allylic position

28
Q

To avoid competition between allylic bromination & ionic addition of Br2 on a double bond _________________ is used as a reagent istead of Br2

A

N-Bromosuccinimide (NBS)

29
Q

Hydrofluorocarbons (HFCs)

A

Are compounds that contain only carbon , flourine, & hydrogen

30
Q

What is the mechanism for Autooxidation?

A
  1. Hydrogen abstraction (Initiation)
  2. Coupling (Propagation)
  3. Hydrogen abstraction (Propagation)
  4. Coupling (Termination)
31
Q

Antioxidants

A

One molecule of a radical scavenger (inhibitor) can prevent the autooxidation of thousands of oil molecules

32
Q

What are the common types of Antioxidants?

33
Q

What is the mechanism for Anti-Markovnikov addition of HX? (Radical addition of HBr to alkenes)

A
  1. Homolytic cleavage (Initiation)
  2. Hydrogen abstraction (Initiation)
  3. Addition (Propagation)
  4. Hydrogen abstraction (Propagation)
  5. Coupling (Termination)
34
Q

An ______________ results in a markovnikov addition

A

Ionic mechanism

35
Q

A ____________ results in an anti-markonvikov addition

36
Q

_________________ can only be accomplished with HBr

A

Anti-markovnikov addition

37
Q

What is the stereochemsitry for radical addition of HBr?

A

Unknown has a racemic mixture

38
Q

What is the mechanism for radical polymerzation?

A
  1. Homolytic cleavage (Initiation)
  2. Addition (Initation)
  3. Addition (Propagation)
  4. Coupling (Termination)
  5. Coupling (Termination)
39
Q

Cracking

A

Converts large alkanes to smaller alkanes

40
Q

Hydrocracking

A

Cracking with H2 to produce alkanes

41
Q

______________ is usually used to add a functional group to an alkane

A

Bromination

Organic Chemistry (47 decks)

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