benzene

• What is the molecular formula for benzene?

  C6H6
• This xylene is in the ortho position

  
• This xylene is in the meta position

  
• This xylene is in the para position

  
• The molecular formula of phenyl is C6H5

  
• Benzyl's molecular formula is CH2-C6H5

  
• What is this monosubstituted benzene?

  A) chloro-benzene

  
• What is the name of this mono substituted benzene?

  A) toluene

  
• What is the name of this monosubstituted benzene?

  A) phenol

  
• What is the name of this monosubstituted benzene?

  A) aniline

  
• What is the name of this monosubstituted benzene?

  A) nitrobenzene

  
• What is the name of this monosubstituted benzene?

  A) benzaldehyde

  
• What is the name of this mono substituted benzene?

  A) benzoic acid

  
• What is the name of this monosubstituted benzene?

  A) acetophenone

  
• What is the name of this mono substituted benzene?

  A) anisole

  
• Name the types of substitution reactions can occur on an aromatic ring.

  A) acylation

  B) alkylation

  C) hydroxylation

  D) sulfonation

  E) nitration

  F) halogenation

  
• For benzene to undergo bromination, Br2 can be catalyzed by FeBr3 to become FeBr4-Br+ which reacts like Br+
• Bromination yields a nonaromantic carbocation intermediate that is doubly allylic and has three resonance forms.

  
• The reaction of an electrophile with a benzene ring is endergonic, requiring substantial activation energy and is usually slow.
• Benzene reactions are slower than alkene reactions due to the stability of benzene

  
• Label this reaction mechanism of the electrophilic bromination of benzene:

  A) slow

  B) fast

  C) HBr

  D) FeBr3

  
• Halogens that can be introduced into aromatic rings include bromine, chlorine, and iodine.
• Fluorine is too reactive to produce fluorobenzene and gives poly-fluorinated products. Fluorobenzene can be made through the schiemann reaction.
• Iodine is unreactive and requires an oxidizing agent to make iodobenzene.
• What type of reaction is this?

  Nitration

  
• What type of reaction is this?


  sulfonation

  
• Friedal-Crafts acylation is used to selectively introduce alkyl substituents and to annelate rings.
• Fill in the blanks of this halogenation reaction:

  A) chlorobenzene

  B) 2

  C) 3

  
• Nitration requires the nitronium ion for the process to start
• Sulfonation requires the formation of a SO3 electrophile to use as an electrophile in the reaction

  
• Formation of the NO2+ electrophile used for nitration


  reaction mechanism:

  
• Fill in the blanks for this reaction mechanism

  A) sulfur trioxide

  B) benzesulfonic acid

  C) base

  D) sulfonation

  
• In a Friedel Crafts reaction, the reaction is carried out by treating an aromatic compound with an alkyl chloride, RCl, using AlCl3 as a catalyst, to generate a carbocation electrophile, R+. Loss of H+ then completes the reaction to add the alkyl to the benzene.

  
• Limitations of the Friedel-Crafts alkylations

  • the carbocation electrophile rearranges under the reaction conditions and the most stable carbocation forms the major the major product
  • the initially formed alkylbenzene is more reactive and polyalkylations are common
  • benzene derivatives with electron withdrawing groups and amino-substituents are nonreactive or give poor yields
• Fill out this chart of EAS reactions

  A) halogenation

  B) nitration

  C) sulfonation

  D) friedel-crafts acylation

  E) friedel-crafts acylation

  
• Activating substituents are ortho and paradirecting
• deactivating groups direct to the meta position
• halogens are deactivating ortho-paradirectors