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Organic Chemistry I Notes

by: Kemjika Echebelem

Organic Chemistry I Notes

Marketplace > Georgia State University > > Organic Chemistry I Notes
Kemjika Echebelem
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Organic Chemistry I

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Hey guys! These are my notes for Ch. 11, Reactions of Alkyl Halides and the second half of Ch. 10, Organohalides for Organic Chem. I. I tried to summarize the most important info. and make it as si...
Organic Chemistry I
Class Notes
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This 2 page Class Notes was uploaded by Kemjika Echebelem on Sunday November 15, 2015. The Class Notes belongs to at Georgia State University taught by in Fall 2015. Since its upload, it has received 6 views.


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Date Created: 11/15/15
Summary of SN1 SN2 E1 E2 amp Ech Rxns SNl SN2 Substitution Nucleophilic 1 molecule determines rate 2 Steps A NuR X91RNu92R NuX39 If there is a chiral center an optically inactive racemic mixture will be made 2 Steps Carbocation Favored when you have Hindered Substrate e g Tertiary Allylic amp Benzylic Halides WeakStrong Neutral Nonbasic ucleophile e g X OH39 Polar Protic Solvent e g H20 to stabilize the carbocation intermediate Leaving Group the best one increases rate by lowering energy of transition state conjugate base of a strong acid e g Cl39 3 alkyl halide is a better substrate than methyl halide because the methyl carbocation would be less stable Methyl lt l lt allylic lt benzylic lt 2 lt 3 Tertiary carbocation is the most stable The most reactive leaving groups are the conjugate bases of strong acids e g I39 is more reactive than Cl39 Primary Allylic amp Benzylic Substrates also can react in SN2 llu T51 E T52 Reaetion Coordinate Substitution Nucleophilic 2 molecules determine the rate 1 Step n 1 2 Nu39 R X 9 Nu R X 9 Nu R X39 o If there is a chiral center its configuration will change Favored when you have Unhindered substrate methyl primary substrate Strong negatively charged nucleophile Polar Aprotic Solvent Leaving Group the best one is a molecule that becomes a more stable anion and lowers the energy of the transition state Vinylic and Aryl Halides are unreactive What can react 9SN2 Reactivity Methyl is most reactive 3 lt Neopentyl lt 2 lt l lt Methyl The best leaving groups for SN2 is similar to that of SNl however uorides ethers alcohols and amines don t undergo 8N2 rxns SiX Solvents to Remember CH3OH H20 DMSO DMF CH3CN HMPA ordered least to greatest reactivity L NuaLo39 Nu39 RLG RN11 LG Reaction Coordinate E1 The E1 Mechanism Br H20 Step 1 2 17 1 H20 Step 2 r H Rate k substrate Analogous to SNl X breaks off followed by attack of the H by a base Follow ZaitseV s Rule When HX is eliminated from an alkyl halide the more substituted alkene will predominate E1 rxn of 2 allylic amp benzylic alkyl halides occurs if a weakly basic nucleophile is used in a protic solution E1 rxn of tertiary alkyl halides occur under neutral conditions No geometic requirement Ech E2 W H 1 fr a E I E39 Analogous to SN2 X is dissociated at the same time H is attacked by the base Deuterium Isotope Effect Rate of CH bond cleavage is faster than CD bond cleavage Requires antiperiplanar geometry Doesn t follow ZaitseV s Rule The E2 can occur as long as there is a base This reaction only occurs if the leaVing group is 2 carbons away from the carbonyl Ech is most common


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