Together with the summary of Simple Functional Group Interconversions and basic carboncarbon bond forming reactions summarized elsewhere, this summary represents all possible reactions that could be encountered on a CHM 234 Final exam. Generating a summary such as this is difficult, since all aspects of the reactions can't be simply summarize, such as stereochemistry, for example. In addition, part of the issue of reactions is recognizing how to use them outside of the context of this summary, and so please use this summary with care and understand that there is more to doing well on the final exam than knowing the reactions here. Br H2 H Pd/C (or Pt or Raney Ni) H CN Na+ –CN Na2Cr2O7 O H oxidation of ALDEHYDE to acid OH SOCl2 alcohol to chloride Cl PBr3 OH SN2 reaction you will generally need to WORK OUT the reagents for SN2 reactions O H2SO4 / H2O OH O reduction of alkenes to alkene alcohol to bromide Br O Na+ –H O– +Na OH NaOH can NOT be used here Br O– +Na O O Williamson ether synthesis HO CH3OH must be an organic acid, HCl, TsOH etc. H+ (cat.) OCH3 OH O CH3OH NaOCH3 CH3O Ph Br CH3OH W + Δ W + H3CO OCH3 + heat W Ph basic conditions gives opposite regiochemistry and other reactions of conjugated systems that have kinetic and thermodynamic products Diels-Alder reaction W Δ Δ and other pericyclic cycloaddition reactions solved using FMO or aromatic transition state theory electrocyclic ring opening/closing solved using FMO or aromatic transition state theory O Zn (Hg) Clemmenson reduction HCl /H2O Et Me 1. KMnO4 / –OH/boil 2. H3 t-Bu NO2 O+ HO2C CO2H t-Bu NH2 H2/Pd/C Br Br2 FeBr3 Cl2 SO3 SO3H electrophilic aromatic substitution sulfonation NO2 electrophilic aromatic substitution nitration H2SO4 O /AlCl3 Cl electrophilic aromatic substitution bromination electrophilic aromatic substitution chlorination H2SO4 HNO3 reduction of nitro to amine, amine synthesis Cl AlCl3 O alkyl oxidation C Friedel-Crafts acylation H C O CO/HCl/AlCl3 O HO OH O O Gatterman Koch reaction acetal formation HCl (cat.) O O O H3O+ H2N C O O Ph C CH3 O acetal hydrolysis Ph Ph formation of imine N H+ (cat.) N H H+ (cat.) N2H4 KOH, heat N Ph formation of enamine CH2 Wolf Kischner reduction O O 1. LDA 2. O Br 1. N 2. H3 alpha-alkylation via enolate using LDA Br Stork enamine alkylation O+ TsOH or Na+–OH O O Aldol condensation, many variants heat O Ph 1. Na+ –OR O + OR 2. H3O+ O O Claisen condensation, many variants Ph CO2H Excess SOCl2 COCl CO2H 1. LiAlH4 OH acid to acid chloride reduction of carboxylic acid to alcohol 2. H3O+ O O Cl O O O HO anhydride synthesis O O EtOH OEt Cl O O NH3 Br O Na+ –CN C N H2O O Cl O H2O O O N C –OH acid chloride hydrolysis no catalyst required –OH O anhydride hydrolysis no catalyst required OH OH O O or H3O+/heat (boil) HO 1. (Excess) LiAlH4 Cl O 2 or H3O+/heat NH2 O nitrile synthesis via SN2 OH O O amide synthesis NH2 Cl O ester synthesis 1. (Excess) LiAlH4 2. H3 O+ ester hydrolysis catalyst required O OH OH 2. H3O+ O OH OH OH amide and nitrile hydrolysis forcing conditions required acid chloride reduction ester reduction H N 1. (Excess) LiAlH4 O 2. H3 C Br amide reduction to form an amine O+ 1. (Excess) LiAlH4 N H N 2. H3O+ 1. NaN3 2. LiAlH4 3. H3 NH2 2. H2/Pd/C CH3NH2/H+ (cat.) O azide reduction to form an amine O+ 1. NH3/H+ (cat.) O nitrile reduction to form an amine NH2 NaBH3CN 1° NH2 NH 2° INDIRECT reductive amination DIRECT reductive amination
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