Electrophilic Aromatic SubstitutionI.Lewis Acid catalystElectrophilic addition of Cl2 or Br2 to an aromatic ring requires the presence of aLewis acid catalyst such as FeCla, FeBr3, AICI3, or AIBR3.a) Why are these compounds considered Lewis acids?b) Why is a Lewis acid catalyst necessary for Cl2 or Br2 to react with an aromaticring?c) Draw the side product which will be formed if you attempt to synthesizechlorobenzene using FeBr3 and Cl2.II. MechanismConsider the mechanism shown below for chlorination of a monosubstituted aromatic ring.CICI-Fe-CÇI FeCl,Fe-CICIFeClaCIÇI FeCla+ HCI + FeCl3a) In this reaction is the aromatic ring behaving as an electrophile or a nucleophile?b) Why is FeCla considered a catalyst in the reaction shown?c) Which would you expect to be faster, an electrophilc aromatic substitution inwhich the Z group is an electron donating group or an electron withdrawing group?Explain your answer.Below is a chart showing common electron donating and withdrawing groups.Electron-Withdrawing Groups (EWG)రంరంరంOHCNO=S=0НОROvery strong EWGElectron-Donating Groups (EDG)RR NHROROHNH2NR2weak EDGvery strong EDG

Only the first question and its first three subparts can be answered as per the rules.

I. Lewis Acid catalyst Electrophilic addition of Cl2 or Br2 to an aromatic ring requires the presence of a Lewis acid catalyst such as FeCl3, FeBr3, AICI3, or AIBR3. a) Why are these compounds considered Lewis acids? b) Why is a Lewis acid catalyst necessary for Cl2 or Br2 to react with an aromatic ring? c) Draw the side product which will be formed if you attempt to synthesize chlorobenzene using FeBr3 and Cl2.

I. Lewis Acid catalyst Electrophilic addition of Cl2 or Br2 to an aromatic ring requires the presence of a Lewis acid catalyst such as FeCl3, FeBr3, AICI3, or AIBR3. a) Why are these compounds considered Lewis acids? b) Why is a Lewis acid catalyst necessary for Cl2 or Br2 to react with an aromatic ring? c) Draw the side product which will be formed if you attempt to synthesize chlorobenzene using FeBr3 and Cl2.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 21E

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