Organic Chemistry 1 Reactions Summary X R NH2 H Cl C Cl C OH C C H C H C H C C C C C H C H C C C LG C LG RO C C ROH C C H HSO4 C C H2 Lindlar s catalyst Li NH3 fast H H2O RO C C H C C R H H C C H C C H O C C R C C R C X R C C C R HX C OH C X C H radical C X X C C C C C C HX dark HX light ROOR 1 BH3 2 R OH H2O2 H H2O C C H2 metal C C C C X2 dark ozone X C H C H C H C H C X C H C X C OH C OH C H C C X C C C O O C All content reactions originate from Carey Francis and Robert Giuliano Organic Chemistry 8th ed New York City McGraw Hill 2011 Print r e d l A s l e i D d r a n g i r G s i s e h t a t e M r e h t E t n e m e g a r r a e R l o c a n P i Organic Chemistry 2 Reactions Summary O COOH R C metal O C H quench C MgBr O C OH C C OH C C s e d i x o p E Br2 H2O OH O H2C CH2 nuc H2C CH2 H2C CH2 O O O nuc nuc less hindered side R MgBr R Li NaBH4 C C more hindereed side H cat CH3OH R2NH H2O C1 C2 C3 C4 C1 C3 C2 C4 C OH H CH3OH R1 OH OH C C R1 R2 H R2 C O C R1 OH R1 C C R2 OH R1 C C R2 R1 R2 R2 H LAH NaBH4 H quench OH C H O C O C O C NaBH4 OH LAH OH O C O OH C H H shift OH R1 R1 C C R2 OH R1 C C R2 R2 R2 R1 REDOX O H C R1 C R2 R2 R2 R1 C R1 O H C KMnO4 H O C OH H C H C H OH PDC OH KMnO4 O C O C C OH no reaction All content reactions originate from Carey Francis and Robert Giuliano Organic Chemistry 8th ed New York City McGraw Hill 2011 Print H OR OR H N R R R H R N R R OH R N H H N H O C O C O C O C OH OH H O O R MgBr CO2 R CH2Br CN H quench H H2O O CR OH O C RH2C OH O C OR O C NR2 O C OR O C O O C O H R OH R R H N H H R OH OH OH H2O R OH O C OH O C OH O C NR2 O C OR O C OH O C NR2 H2O OH H quench O C OH g i t t i O CW R2CPPh3 C C R R n o i t a l y x o b r a c e D O C O C OH O C CO2 O C OH O C R OH 1 SOCl2 2 ROH 3 Et2O Et3N H2CNN O C OR O R O CH3 O C OR non aq nuc H quench OH nuc nuc nuc O CR H2C NR2 O C nuc OH nuc nuc O CR OR nuc O C NR2 LAH nuc non aq nuc O C Cl O C Cl O C Cl O C Cl i e d m A b e r n i e W O O LAH N O R CH3 N O R CH3 non aq nuc O C H O C CH3 All content reactions originate from Carey Francis and Robert Giuliano Organic Chemistry 8th ed New York City McGraw Hill 2011 Print O C O C O O R1 R1 R1 R2 O C O C O C nuc O C R O R R nuc O R O C O C OH R1 OH OH R2 Cl R1 R1 O C O C O C R CN R CN O C nuc nuc LAH H quench H R C nuc NH2 H H2O H quench R nuc C O R CN H H2O O C R OH O C l o d A l CH CH OH O C continue n o i t a l y k l a o n o m t c u d d a l e a h c i M n o s n i b o R O C O C O C O n O C o i t a l y k l a CH OD D2O OD C D D D D D D O C O C LDA CH CH3Br O C O R R CuLi O C O O Aldol continue R O OR H2O O C O C OH O C O O H O continue H2O OCH3 HO O OCH3 O n e s i a l C m u i r b i l i u q e l o n e o t e k O C OR O O OR C H OR C H OR OH O C CH OH C can also happen in H O OCH3 O C H Br2 CH3O O C All content reactions originate from Carey Francis and Robert Giuliano Organic Chemistry 8th ed New York City McGraw Hill 2011 Print H2SO4 HNO3 Br2 FeBr3 NO2 Br s t f a r C l e d e i r F FeCl3 C Cl O C R Cl FeCl3 O O R R H2NNH2 OH H Zn Hg C O R R R C H2 C H2 All content reactions originate from Carey Francis and Robert Giuliano Organic Chemistry 8th ed New York City McGraw Hill 2011 Print
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