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Organic chemistry Notes Chapter 17 and 18

by: Megan steltz

Organic chemistry Notes Chapter 17 and 18 Chem 372-0

Marketplace > Eastern Michigan University > Chemistry > Chem 372-0 > Organic chemistry Notes Chapter 17 and 18
Megan steltz
GPA 3.28

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these notes cover benzene the nomenclature associated with it, its different structures and all the different types of reactions it can undergo
Organic Chemistry
Gregg M. Wilmes
Class Notes
Organic Chemistry, Benzene, nomenclature, reactions
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This 15 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 6 views. For similar materials see Organic Chemistry in Chemistry at Eastern Michigan University.

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Date Created: 10/07/16
Chapter 17 part 2 Reactions of benzene Benzene is unexpectedly stable Or Measure relative energy of unsaturated compounds by hydrogenation C=C +H2 = C-C Lose C-C π gain 2x C-H σ H – H σ ● Products more stable than reactants ● Exothermic reaction ΔH = -120 KJ/mol ΔH = -232 KJ/mol (8 KJ/mol of stabilization from conjugation) ΔH = - 208 KJ/mol (152 KJ/mol of stabilization from conjugation) Extra stabilization results from aromaticity Aromatic molecules (or groups) 1. cyclic 2. planar 3. conjugated 4. has specific # of π electrons examples of not aromatic molecules hexatriene not aromatic not cyclic cyclooctatetraene Not planar not aromatic For a molecule to be conjugated all atoms must have unhybridized p-orbital sp^2 or sp Huckels Rule All aromatic groups have 4n+2 π electrons where n is an integer 2,6,10,14,18,22… All possible numbers of π electrons an aromatic compound can have Cyclic, planar, conjugated molecules with 4n π electrons are unstable antiaromatic Aromatic = cyclic, planar, conjugated 4n + 2 π e- Antiaromatic = cyclic, planar, conjugated, 4n π e- Non-aromatic = fails any one of all 4 criteria [14] - annulene 14 π e- Polycyclic aromatic hydrocarbons Aromatic molecules with heteroatom (O, N, S) Things to remember ● look for Sp^2 hybridized carbons ● count π bonds in 4n + 2 pattern 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 3) Friedel-Crafts Alkylation 4) Friedel-Crafts 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 Friedel-Crafts Alkylation 1º alkyl halide = no carbocation Limitations of F-C 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 R-Cl 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 substituent


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