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Chem: Organic Chemistry And Analysis > 25.2 electrophilic substitution reactions of benzene > Flashcards

25.2 electrophilic substitution reactions of benzene Flashcards

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1
Q

what type of mechanism does benzene undergo?

A

electrophilic substitution

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2
Q

conditions and reagents for the nitration of benzene

A
  • sulfuric acid catalyst
  • heated to 50c
  • nitric acid
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3
Q

what would happen if the nitration of benzene was taken place at above 50c?

A

further substitution reactions occurs

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4
Q

how is the electrophile NO2+ formed?

A

HNO3 + H2SO4 -> NO2+ + HSO4- + H2O

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5
Q

how is the sulfuric acid regenerated?

A

H+ + HSO4- -> H2SO4

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6
Q

draw the electrophilic substitution reaction of the nitration of benzene

A

page 438

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7
Q

name the 4 common halogen carriers

A
  • FeCl3
  • AlCl3
  • AlBr3
  • FeBr3
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8
Q

how is the electrophile Br+ formed?

A

Br2 + FeBr3 -> FeBr4- + Br+

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9
Q

how is the halogen carrier regenerated in the bromination of benzene reaction?

A

H+ + FeBr4- -> FeBr3 + HBr

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10
Q

draw the electrophilic substitution reaction of the bromination of benzene

A

page 439

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11
Q

what is an electrophile?

A

electron pair acceptor

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12
Q

what are the conditions and reagents for the bromination of benzene?

A
  • AlBr3/ FeBr3
  • Br2
  • room temperature
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13
Q

what are the conditions and reagents for the chlorination of benzene?

A
  • AlCl3/ FeCl3
  • Cl2
  • room temperature
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14
Q

how is the electrophile Cl+ formed?

A

Cl2 + FeCl3 -> FeCl4- + Br+

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15
Q

how is the halogen carrier regenerated in the chlorination of benzene reaction?

A

H+ + FeCl4- -> FeCl3 + HCl

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16
Q

draw the electrophilic substitution reaction of the chlorination of benzene

A

page 439

17
Q

what is the alkylation of benzene?

A

substitution of a hydrogen atom in the benzene ring by an alkyl group

18
Q

what is alkylation and acylation of benzene also called?

A

Friedel- Crafts reactions

19
Q

what is the acylation of benzene?

A

substitution of a hydrogen atom in the benzene ring by a ketone

20
Q

what are the conditions and reagents for the alkylation of benzene?

A
  • haloalkane

- halogen carrier

21
Q

what are the conditions and reagents for the acylation of benzene?

A
  • acyl chloride

- halogen carrier

22
Q

explain the relative resistance to bromination of benzene compared to alkenes

A
  • In benzene, pi-bond(s) are delocalised 
  • In alkenes, pi-bond is localised between two carbons
  • benzene has a lower electron density
  • alkene/C=C has a higher electron density 
  • benzene polarises bromine less
23
Q

draw the electrophilic substitution reaction of the alkylation of benzene

A

page 440

24
Q

draw the electrophilic substitution reaction of the acylation of benzene

A

page 440

Chem: Organic Chemistry And Analysis (21 decks)

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