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Organic Chemistry Chapter 18

by: Megan steltz

Organic Chemistry Chapter 18 Chem 372-0

Marketplace > Eastern Michigan University > Chemistry > Chem 372-0 > Organic Chemistry Chapter 18
Megan steltz
GPA 3.28

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these notes cover chapter 18 which discus the reactions of benzene this is the word file of the pdf uploaded earlier it is the exact same expect that there was some problem with the reaction arr...
Organic Chemistry
Gregg M. Wilmes
Class Notes
Organic Chemistry, Benzene
25 ?




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This 10 page Class Notes was uploaded by Megan steltz on Friday October 7, 2016. The Class Notes belongs to Chem 372-0 at Eastern Michigan University taught by Gregg M. Wilmes in Fall 2016. Since its upload, it has received 5 views. For similar materials see Organic Chemistry in Chemistry at Eastern Michigan University.

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Date Created: 10/07/16
Chapter 18 Electrophlic aromatic substitution  Aromatic compounds are electron rich  o Many electrons in π orbital o π bonds are less stable than σ bonds  o aromaticity is retained in the product  Mechanism of electrophlic aromatic substitution  There are two more possible resonance structures for the above molecule  5 different types of reactions with aromatic compounds  1) Halogenation  2) Nitration  3) Sulfonation  4) Friedelcrafts Alkylation 5) Fridelcrafts Acylation  Review of Lewis Dot/Resonance Structures  H’s attached to carbons are not shown but they are still there  No more than 8e­ on C, N, O  Lone pairs are optional, charges are required  Resonance structures, differ in the location of  o Lone pairs o π bonds  o atoms and σ bonds do not change     Shows movement of e­ always start the arrow at the bond (σ or π) or a lone pair.  End of arrow must point to atom or bond making new π bond Halogenation  Reacts with Cl2 or Br2  Catalyst is FeCl3 or FeBr3  Reaction forms electrophile Nitration and Sulforation  HNO3 reagent  H2SO4 catalyst Sulfonation  Reactions contains SO3 with H2SO4  Always going to be SO3 + H2O = H2SO4 fuming sulfuric acid  Friedel­Crafts Alkylation   1º alkyl halide = no carbocation  Limitations of F­C Alkyation Does not work if halogen is attached to Sp2 or Sp3 hybridized carbons. Carbocations in F.C. alkylation are prone to rearrangement problems with 1º or 2º R­Cl EAS or Substituted compounds  The identity of the z, controls whether ortho, meta or para product(s) are  formed  Group already on the ring decides whether the reaction happens  Some substitutions (activators) speed up the rate of EAS (relative to benzene)  some (deactivators) slow down the rate. Activating/ deactivating directing effects  Determined an electron withdrawing r donating capabilities of  substance.   Electron donating groups are activators  Examples.  Electron withdrawing groups are deactivating  Electron donating or withdrawing can occur by  Inductive effects resulting in differences in electronegativty  Occur through σ bonds Alkyl groups are inductively donating Heteroatoms (O, N, X) are more electronegative than H so they are inductively  withdrawing. Resonance effects  Groups allow resonance structures that put + or – into ring   Resonance donating group places negative charge in ortho and para position   For O, N resonance donating is stronger than inductive withdrawing With ­F, ­Cl, ­Br, ­I inductive effects are stronger than resonance donating  Resonance withdrawing groups  Example  + is ortho or para to subsistent 


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