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CHM 234| Aromatic compound (cont.) and Aromatic Reactions

by: Alvin Notetaker

CHM 234| Aromatic compound (cont.) and Aromatic Reactions CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Aromatic compound cont and Aromatic Reactions
Alvin Notetaker
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Topic: Aromatic (cont.) Chapter 19 : Aromatic Reactions
General Organic Chemistry II
Class Notes
Organic Chemistry
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This 10 page Class Notes was uploaded by Alvin Notetaker on Sunday March 27, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 9 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.

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Date Created: 03/27/16
Aromatic compounds (cont.)    Antiaromatic  Similar to to aromatics’ criteria, but it needs even number of pi electrons pair.    Aromatic compound other than Benzene  Nonaromatic Compounds  A compound that lacks a continuous systems of p orbitals.  Example​ :                                                      Annulenes­ ​ ring system that are fully conjugated.    [10] Annulenes   Nonaromatic      Aromatic  Antiaromatic  4n+2  4n    Example:           Aromatic                                                          Antiaromatic         Antiaromatic       Nonaromatic    Example:                                               Nonaromatic                Aromatic                  Antiaromatic    Aromatic ion  Some ring carry formal charge        Aromatic Heterocycles  Heteroatoms are other atoms that are within the ring other than C or H.        Polycyclic Aromatic Compounds  More than one ring system together.      Reactions of Benzylic Position  A carbon that is attached to a benzene ring is benzylic                Oxidation      The benzylic position needs at least one proton.      Free Radical Bromination      Substitution Reactions of Benzylic Halides        Elimination Reactions      Reduction of Aromatic Moiety  Hydrogenation  Benzene can be reduced only in a forceful manner. (At 100 atm and 150 °C)      Chapter 19 Aromatic Substitution Reactions    Introduction  Halogenation with benzene doesn’t work.  To make a substitution, a lewis acid must be introduce.    Halogenation  This reaction uses mostly bromine and chlorine.  This reaction requires a lewis acid catalyst.   Lewis acid compound use: FeCl​ 3​and AlCl​ 3    Mechanism:      With iodine, CuCl​  is needed for this type of reaction.  2​   Sulfonation    Fuming H​ 2​​ 4​consist of sulfuric acid and SO3​gas.  Mechanism:      Depending on the concentration of the sulfuric acid:  Concentrated = forward reaction  Diluted = reverse reaction     Nitration  A mixture of sulfuric acid and nitric acid      Mechanism:      Reduction a Nitro Substituent  Reagent​ :  H , Pt  2 Fe, HCl  Sn, HCl    Nitro group to an amine group    Friedel­Crafts Alkylation    Mechanism:      As for primary halide, they cannot convert into a carbocation since primary halide are very high  in energy. So, they undergo h ​ydride shift​.    Friedel­Crafts Alkylation Limitation  1. Halide must be attached to a sp​ 3 hybridized carbon.  2. Polyalkylation can occur.  ● More than one substituents can form on the benzene  3. Some substituted aromatic rings are too deactivated to react.  ● Substituents that withdraws electrons. This is called deactivation.    Friedel­Crafts Acylation  Forms carbon­carbon bond    Mechanism:    ● Acylium ion, R­C​ +=O, is stabilized by resonance.      Clemmensen Reaction      Activating Group  Substituents that are good electron donating group like nitration reaction.    Deactivation Group  Substituents that are good electron withdrawing group like nitration reaction.  Nitro group is a good withdrawing group.    The ortho and para formation created a two positive partial charge next to each other which will  create an unstable bonding. So, only meta is the most stable of the three formation.    So, for major products:  Donating group = ortho and para products  Withdrawing group = meta products 


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