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Organic Chemistry

by: Chandler Schoen

Organic Chemistry CHEM 251

Chandler Schoen
GPA 3.58


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Class Notes
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This 4 page Class Notes was uploaded by Chandler Schoen on Monday September 21, 2015. The Class Notes belongs to CHEM 251 at Ohio State University taught by Staff in Fall. Since its upload, it has received 14 views. For similar materials see /class/210009/chem-251-ohio-state-university in Chemistry at Ohio State University.


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Date Created: 09/21/15
orgame ehemtstxy s2E2s 1E1 squot SydEl e eleitxophlle yteepme substrate leamnggoup N Nurc a a m b vg NUL 510W 9 Ce e A Lice a L VNU N l 1 V Ax sameumes k H U substrate leavmg youp wah A C 7 7 and E1 electropth H QB 6 p1 33 Va cc H78 B L FeccR H78 1 T 2 SM and E1 have tdentzeat rate detemmmg steps so they WE 9 generally occur stmultaneously and have the same propemes wwwfreelanc t acher eom organic chemistry SN2 E2 SNl El nucleophilicity Nu resonance worse Nu is basicity stronger resonance leaving group ability LG resonance nucleophilicity Nu basicity stronger leaving group ability LG nucleophile leaving groups bases nucleophiles leaving groups N 0 F N39 039 Fquot good Nu 3N2 or 3N1 N o F E N 0 good LG P S Cl39 oor Nu S l onl P S Cl 3 P 7 not a LG P e 5 Se39 Br39 got a Nu N Y Br Em R OR I I39 I O The a carbon is attached to cyanide NC39 charge on the C not the N the oxygen Qt t0 the sum bases Nucleophiles and bases shown with charges before attacking N O F N39 039 strong base E2 Leaving groups shown with charges before leaving P S Gl P39 S39 Gl weak base E1 The tables for individual atoms assume no resonance Resonance Br Brquot not a base makes atoms into worse nucleophiles and bases and into better leaving I F groups 2 wwwfreelanceteachercom organic chemistry 8N2 E2 SNl E1 One or Step one or two or carbon Step one group or two Base takes TE bond forms between or and carbons poor Nu good Nu weak base good Nu strong base weak base N S Se Cl39 Br39 I39 NC39 839 Se39 0 non bulky bulky OR BASE 1 means SNl E1 occur SNl to E1 mentioned The E1 reactions become more important at high temperatures The table displays the major reaction for each caseiin some cases there may be signi cant levels of minor competing reactions The table may not give the correct answer in all realworld situations but it will generally be accurate for the questions that are typical of exams 95 to 5 so E1 not wwwfreelanceteachercom organic chemistry 8N2 E2 SNl El how to determine 8N2 vs E2 vs SNl vs El for alcohol substrates First the alcohol must be treated with an acid to give it a better leaving group ACID nonnucleophilic acid nucleophilic acid H2804 HCl HBr HI First acid protonates an alcohol to form a good leaving group First acid protonates alcohol to form a good leaving For substitution another alcohol acts as nucleophile group For elimination you can use another alcohol or HSO439 as base Then Cl39 Br39 or I39 act as nucleophiles or bases uCARBON methyl SN2 needs A SN2 no reaction with Cl39 1 SN2 needs A SN2 no reaction with Cl39 E2 needs more A 2 SNlEl SNJEJ El dominant with A El dominant with A 3 SNlEl SNlEl El dominant with A El dominant with A The information in italics indicates characteristics that differ from what we would expect for haloalkane substrates The most important new reactivity for alcohols is that treatment of secondary and tertiary alcohols with H2804 plus heat gives El this reaction is called dehydration High temperatures favor El over SNl for haloalkanes as well but this is rarely tested Ethers have mostly similar reactivity to alcohols HBr and HI attack ethers to form alcohols which can then be attacked by more HBr or HI to form haloalkanes SNlEl means both SNl and El occur In these cases the ratio of SNl to E1 is generally about 95 to 5 so the El reaction is often not mentioned But as mentioned above at high temperatures E1 is dominant The table displays the major reaction for each caseiin some cases there may be significant levels of minor competing reactions The table may not give the correct answer in all situations but it will generally be accurate for the questions that are typical of exams 4 wwwfreelanceteachercom


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