//DATA.JS
lastupdated="9:35 PM September 02, 2003"
Topics=new Array(""
,[1,"Electronic Structure and Bonding"]
,[1,"Acids and Bases"]
,[2,"An Introduction to Organic Compounds"]
,[3,"Reactions of Alkenes"]
,[4,"Stereochemistry"]
,[5,"Reactions of Alkynes"]
,[6,"Electron Delocalization and Resonance"]
,[7,"Reactions of Dienes"]
,[8,"Reactions of Alkanes"]
,[9,"Substitution Reactions of Alkyl Halides"]
,[10,"Elimination Reactions of Alkyl Halides"]
,[11,"Reactions of Alcohols, Amines, and Related Compounds"]
,[12,"Mass Spectrometry"]
,[12,"Infrared Spectroscopy"]
,[12,"UV/Visible Spectroscopy"]
,[13,"NMR Spectroscopy"]
,[14,"Aromatic Compounds"]
,[15,"Reactions of Substituted Benzenes"]
,[16,"Reactions of Carboxylic Acids and Carboxylic Acid Derivatives"]
,[17,"Reactions of Aldehydes and Ketones"]
,[18,"Oxidation and Reduction of Organic Compounds"]
,[19,"Reactions Involving Enols, Enolates, and Related Species"]
,[20,"Carbohydrates"]
,[21,"Amino Acids, Peptides, and Proteins"]
,[22,"Catalysis"]
,[23,"Biochemical Catalysis Involving Coenzymes"]
,[24,"Lipids"]
,[25,"Nucleosides, Nucleotides, and Nucleic Acids"]
,[26,"Synthetic Polymers"]
,[27,"Heterocyclic Compounds"]
,[28,"Pericyclic Reactions"]
,[29,"Multistep Organic Synthesis"]
,[30,"Drug Discovery and Design"]
)
Groups=new Array(['any']
,["RH","alkane","RR'"]
,["RR' ","alkane",""]
,["alkene","alkene",""]
,["alkyne","alkyne",""]
,["RX","aliphatic halides","RF, RCl, RBr, RI, ROTs, R'X, R'Br"]
,["R'X","aliphatic halides",""]
,["RF","aliphatic fluoride",""]
,["RCl","aliphatic chloride",""]
,["RBr","aliphatic bromide",""]
,["R'Br","aliphatic bromide",""]
,["RI","aliphatic iodide",""]
,["ROH","aliphatic alcohols",""]
,["ROR","aliphatic ether","ROR'"]
,["ROR'","aliphatic ether",""]
,["ROTs","aliphatic tosylate","R'OTs"]
,["R'OTs","aliphatic tosylate",""]
,["RCHO","aliphatic aldehydes",""]
,["R2C=O","aliphatic ketones",""]
,["RCO2H","aliphatic acid",""]
,["RCO2R","aliphatic ester",""]
,["RCN","aliphatic nitrile",""]
,["RSH","aliphatic thiol",""]
,["RSR","aliphatic thioether",""]
,["R3S+X-","sulfonium salt",""]
,["epoxide","epoxide",""]
,["RLi","organolithium compound",""]
,["RMgBr","Grignard reagent",""]
,["R2CuLi","Gilman reagent",""]
,["amine","amine","RNH2, R2NH, R3N"]
,["RNH2","primary amine",""]
,["R2NH","secondary amine",""]
,["R3N","tertiary amine",""]
,["R4N+X-","quaternary ammonium salt","RN(CH3)3+I-"]
,["R3NO","tertiary amine oxide",""]
,["acyl halide","acyl halide",""]
,["acid anhydride","acid anhydride",""]
,["amide","amide",""]
,["imine","imine",""]
,["oxime","oxime",""]
,["hydrazone","hydrazone",""]
,["semicarbazone","semicarbazone",""]
,["enamine","enamine",""]
)
// reactant, conditions, product, comment, disallow, Bruice3 chapter, section, [BRUICE4 REFS as [chapter,page]], [WADE REFS as [chapter,page],[chapter,page],[chapter,page]]
Data=new Array(""
,["alkene","1. conc. H2SO4;2. H2O, heat","alcohol","very harsh conditions",2,3,0,[[0,0]],[[8,322],[0,0],[0,0]]]
,["alkene","ICH2ZnI","cyclopropane","Simmons@-Smith reaction",0,3,0,[[0,0]],[[8,337],[0,0],[0,0]]]
,["alkene|wade2","CHBr3;KOH, H2O","RBr|wade3","alpha elimination",0,3,0,[[0,0]],[[8,337],[0,0],[0,0]]]
,["alkene|da32","HBr, HCl, or HI","RBr, RCl, RI|da37","Markovnikov addition;of a hydrogen halide;X = Br, Cl, I",0,3,8,[[4,148]],[[8,317],[0,0],[0,0]]]
,["alkene|da32","H2O, catalytic H2SO4","ROH|da33","acid@-catalyzed Markovnikov; addition of water is very harsh!",0,3,13,[[4,151]],[[8,322],[0,0],[0,0]]]
,["alkene|da32","ROH, catalytic H2SO4","ROR'|da34","acid@-catalyzed Markovnikov; addition of an alcohol is very harsh!",0,3,13,[[4,153]],[[14,612],[0,0],[0,0]]]
,["alkene|da32","Br2 or Cl2, CH2Cl2","RBr, RCl|da38","addition of halogen;X = Br, Cl",0,3,15,[[4,157]],[[8,338],[0,0],[0,0]]]
,["alkene|da32","Br2 or Cl2, H2O","ROH, RBr, RCl|da39","addition of a halogen;with opening by water;X = Br, Cl",0,3,15,[[4,159]],[[8,341],[0,0],[0,0]]]
,["alkene|da32","Br2 or Cl2, R'OH","ROR', RBr, RCl|da40","addition of a halogen;with opening by alcohol;X = Br, Cl",0,3,15,[[4,160]],[[0,0],[0,0],[0,0]]]
,["alkene|da32","Br2, NaCl","RBr, RCl|da41","addition of a halogen;with opening by chloride",0,3,15,[[4,160]],[[8,343],[0,0],[0,0]]]
,["alkene|da32","1. Hg(OAc)2, H2O, THF;2. NaBH4, HO-","ROH|da33","oxymercuration--demercuration##;Markovnikov addition;is not as harsh as H2SO4",0,3,16,[[4,161]],[[8,324],[0,0],[0,0]]]
,["alkene|da32","1. Hg(O2CCF3)2, R'OH, THF;2. NaBH4, HO-","ROR'|da34","oxymercuration--demercuration##;Markovnikov addition;is not as harsh as H2SO4",0,3,16,[[4,162]],[[8,326],[0,0],[0,0]]]
,["alkene|da32","1. Hg(OAc)2, R'OH;2. NaBH4, HO-","ROR'|da34","oxymercuration--demercuration##;Markovnikov addition;is not as harsh as H2SO4",0,3,0,[[0,0]],[[8,326],[0,0],[0,0]]]
,["alkene|da32","1. BH3, THF;2. H2O2, HO-, H2O","ROH|da35","hydroboration--oxidation##;anti@-Markovnikov addition",0,3,17,[[4,163]],[[8,328],[0,0],[0,0]]]
,["alkene|da32","HBr, peroxide","RBr|da36","radical addition;anti@-Markovnikov addition;peroxide = H2O2 or ROOR",0,3,18,[[4,167]],[[8,319],[0,0],[0,0]]]
,["alkene|da32","H2; Pd/C, Pt/C, or Ni","RH|da32a","hydrogenation of an alkene",0,3,19,[[4,171]],[[8,333],[0,0],[0,0]]]
,["alkyne|2pentyne","KMnO4;H2O, neutral","R2C=O|dione","permanganate oxidation of an alkyne;under neutral conditions;gives a @1,@2@-diketone",0,5,0,[[0,0]],[[9,394],[0,0],[0,0]]]
,["alkyne|2butyne","KMnO4, KOH","RCO2H|wade7","permanganate oxidation of an alkyne;under basic conditions;results in cleavage",0,5,0,[[0,0]],[[9,394],[20,918],[0,0]]]
,["alkyne|da42","1 equivalent of HCl or HBr","RCl, RBr, alkene|da44","Markovnikov addition;of a hydrogen halide;X = Br, Cl",0,5,5,[[6,243]],[[9,389],[0,0],[0,0]]]
,["alkyne|da42","excess HCl or HBr","RCl, RBr|da46","Markovnikov addition;of a hydrogen halide;X = Br, Cl",0,5,5,[[6,243]],[[9,390],[0,0],[0,0]]]
,["alkyne|da42","1 equivalent of Br2 or Cl2; CH2Cl2","RBr, RCl,/,alkene|da45","addition of halogen;X = Br, Cl",0,5,5,[[6,245]],[[9,388],[0,0],[0,0]]]
,["alkyne|da42","excess Br2 or Cl2, CH2Cl2","RBr, RCl|da48","addition of halogen;X = Br, Cl",0,5,5,[[6,245]],[[9,389],[0,0],[0,0]]]
,["alkyne|da42","HBr, peroxide","RBr,/,alkene|da47","radical addition##;anti@-Markovnikov addition##;peroxide = H2O2 or ROOR",0,5,5,[[6,245]],[[9,390],[0,0],[0,0]]]
,["alkyne|da43","H2O, H2SO4","R2C=O|da49","addition of water##;formation of a ketone;from an internal alkyne",0,5,6,[[6,246]],[[0,0],[0,0],[0,0]]]
,["alkyne|da42","H2SO4, catalytic HgSO4","R2C=O|da50","addition of water##;formation of a methyl ketone;from a terminal alkyne",0,5,6,[[6,247]],[[9,391],[0,0],[0,0]]]
,["alkyne|da43","1. BH3, THF;2. H2O2, HO-, H2O","R2C=O|da49","hydroboration--oxidation;of an internal alkyne;will give both possible ketones",0,5,7,[[6,248]],[[9,392],[0,0],[0,0]]]
,["alkyne|da42","1. disiamylborane, THF;2. H2O2, HO-, H2O","RCHO|da51","hydroboration--oxidation using a hindered borane##;anti@-Markovnikov addition;of a terminal alkyne to form an aldehyde",0,5,7,[[6,248]],[[9,392],[0,0],[0,0]]]
,["alkyne|da52","H2;Pd/C, Pt/C, or Ni","RCH2CH2R',/,RH","hydrogenation of an alkyne;to form an alkane",0,5,8,[[6,249]],[[9,386],[0,0],[0,0]]]
,["alkyne|da52","H2;Lindlar's catalyst","alkene|da53","hydrogenation of an alkyne;to form a cis@-alkene",0,5,8,[[6,249]],[[9,386],[0,0],[0,0]]]
,["alkyne|da52","Na or Li;NH3(liq)","alkene|da54","reaction of an alkyne;to form a trans@-alkene",0,5,8,[[6,250]],[[9,387],[0,0],[0,0]]]
,["alkyne,/,RBr, RCl, RI|da42","1. NaH or NaNH2;2. R'X","alkyne|da52","alkylation of acetylide ion##;X = Br, Cl, I",0,5,10,[[6,253]],[[9,378],[0,0],[0,0]]]
,["alkene|da3","HCl","RCl,/,alkene|da4","addition of HCl to an isolated diene",0,7,6,[[8,304]],[[0,0],[0,0],[0,0]]]
,["alkene|da5","HBr, --80 oC","RBr,/,alkene|da6","low temperature favors the kinetic product",0,7,8,[[8,308]],[[15,645],[0,0],[0,0]]]
,["alkene|da5","HBr, 45 oC","RBr,/,alkene|da7","high temperature favors the thermodynamic product",0,7,8,[[8,309]],[[15,645],[0,0],[0,0]]]
,["alkene|da1","heat","alkene|da2","Diels--Alder reaction;forms 2 C--C bonds",0,7,9,[[8,313]],[[15,655],[0,0],[0,0]]]
,["RH","Cl2; heat or light","RCl","radical chlorination;is not very selective",0,8,2,[[9,338]],[[4,124],[0,0],[0,0]]]
,["n@-butane,/,RH","Br2; heat or light","2@-bromobutane,/,RBr","radical bromination;is very selective",0,8,2,[[9,338]],[[4,148],[0,0],[0,0]]]
,["alkene|da8","NBS;light or heat;CH2Cl2","RBr,/,alkene|da9","radical allylic bromination,;using N@-bromosuccinimide",0,8,5,[[9,346]],[[15,650],[0,0],[0,0]]]
,["RH|da10","HBr","RBr|da11","reaction of a strained cycloalkane with HBr",0,8,7,[[0,0]],[[0,0],[0,0],[0,0]]]
,["RH|da10","Cl2, FeCl3","RCl|da12","reaction of a strained cycloalkane with Cl2",0,8,7,[[0,0]],[[0,0],[0,0],[0,0]]]
,["RH|da10","H2, Ni, 80 oC","RH|da13","hydrogenation of a strained cycloalkane",0,8,7,[[0,0]],[[0,0],[0,0],[0,0]]]
,["RH|da14","H2, Ni, 200 oC","RH|da15","hydrogenation of a strained cycloalkane",0,8,7,[[0,0]],[[0,0],[0,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","excess NH3","CH3CH2NH2,/,RNH2","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[0,0]],[[6,227],[19,881],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","N3-","CH3CH2N3,/,RN3","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[0,0]],[[6,227],[19,882],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","CH3CO2-","RCO2R|meco2et","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[0,0]],[[6,227],[0,0],[0,0]]]
,["CH3CH2Br,/,RX,RBr","NaI;acetone","CH3CH2I,/,RX,RI","acetone is used to;precipitate the NaBr byproduct",2,9,0,[[0,0]],[[6,228],[0,0],[0,0]]]
,["CH3CH2Cl,/,RX,RCl","KF, 18@-crown@-@6;CH2CN","CH3CH2F,/,RX,RF","crown ether is used to;enhance the ;nucleophilicity of F-",2,9,0,[[0,0]],[[6,228],[0,0],[0,0]]]
,["RX,ROH|da39","=-OH","epoxide|wade6","the starting halohydrin;can be made from the alkene",0,9,0,[[0,0]],[[14,620],[0,0],[0,0]]]
,["CH3CH2Cl,/,RCl","NaOH","CH3CH2OH,/,ROH","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[10,362]],[[6,227],[0,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","=-NH2","CH3CH2NH2,/,RNH2","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[10,372]],[[0,0],[0,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","NaSH","CH3CH2SH,/,RSH","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[10,372]],[[6,227],[0,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","NaOCH3","CH3CH2OCH3,/,ROR'","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[10,372]],[[6,227],[11,478],[14,610]]]
,["CH3CH2X,/,RBr, RCl, RI","NaSCH3","CH3CH2SCH3,/,RSR'","S_N@2 reaction;of a primary or secondary;alkyl halide",2,9,4,[[10,372]],[[6,227],[0,0],[0,0]]]
,["RX,/,RBr, RCl, RI","NaC2R'","alkyne|da52","S_N@2 reaction by acetylide;at a primary or secondary;alkyl halide;forms a C--C bond",2,9,4,[[10,372]],[[6,227],[9,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","NaCN","CH3CH2CN,/,RCN","S_N@2 reaction at a primary;or secondary alkyl halide;forms a C--C bond",2,9,4,[[10,372]],[[6,227],[19,883],[0,0]]]
,["CH3CH2NH2,/,RNH2,RI","excess CH3I, K2CO3","CH3CH2N(CH3)3+I-,/,RN(CH3)3+I-,R4N+I-","formation of a;quaternary ammonium salt",0,9,4,[[10,374]],[[19,858],[0,0],[0,0]]]
,["(CH3CH2)2NH,/,R2NH,RI","excess CH3I, K2CO3","(CH3CH2)2N(CH3)2+I-,/,R2N(CH3)2+I-,R4N+I-","formation of a;quaternary ammonium salt",0,9,4,[[10,374]],[[19,858],[0,0],[0,0]]]
,["(CH3CH2)3N,/,R3N,RI","excess CH3I","(CH3CH2)3NCH3+I-,/,R3NCH3+I-,R4N+I-","formation of a;quaternary ammonium salt",0,9,4,[[10,374]],[[19,858],[0,0],[0,0]]]
,["RBr|r3cbr","H2O, heat","ROH|r3coh","S_N@1 reaction with a tertiary alkyl halide ",0,9,5,[[10,375]],[[6,238],[0,0],[0,0]]]
,["RBr|wade1","NaI,acetone;or;Zn,CH3CO2H","alkene|wade2","reduction;of a vicinal dibromide",0,10,0,[[0,0]],[[7,296],[0,0],[0,0]]]
,["RX,/,RBr, RCl, RI, ROTs","base","alkene","E@2 elimination##;X = OTs, I, Br, Cl",0,10,1,[[11,401]],[[6,252],[0,0],[0,0]]]
,["RBr|da20","NaOH, H2O","alkene|da21","Zaitsev elimination;via an E@2 mechanism",0,10,1,[[11,402]],[[6,253],[0,0],[0,0]]]
,["RBr|da16","NaOCEt3","alkene|da17","bulky bases give predominantly;non@-Zaitsev alkene;in an E@2 reaction",0,10,2,[[11,405]],[[7,292],[0,0],[0,0]]]
,["RF|da18","NaOCH3, CH3OH","alkene|da19","fluorides give predominantly;non@-Zaitsev E@2 elimination",0,10,2,[[11,407]],[[0,0],[0,0],[0,0]]]
,["RBr, RCl|da55","NaNH2","alkyne|da52","E@2 elimination##;X = Br, Cl",0,10,10,[[11,427]],[[9,382],[0,0],[0,0]]]
,["alcohol","conc. H2SO4 or H3PO4;heat","alkene","very harsh conditions",2,11,0,[[0,0]],[[7,300],[11,464],[0,0]]]
,["NaSH","RX,/,RBr, RCl, RI","CH3SH,/,RSH","SN@2 reaction of hydrosulfide ion",0,11,0,[[0,0]],[[10,438],[0,0],[0,0]]]
,["2 CH3CH2SH,/,RSH","Br2","CH3CH2SSCH2CH3,/,RSSR","mild oxidation of a thiol; gives a disulfide",0,11,0,[[0,0]],[[10,439],[0,0],[0,0]]]
,["CH3CH2SSCH2CH3,/,RSSR","Zn, HCl","2 CH3CH2SH,/,RSH","reduction of a disulfide; gives a thiol",0,11,0,[[0,0]],[[10,439],[0,0],[0,0]]]
,["CH3CH2SH,/,RSH","KMnO4 or HNO3","CH3CH2SO2H","harsh oxidation of a thiol; gives a sulfonic acid",0,11,0,[[0,0]],[[10,439],[0,0],[0,0]]]
,["ROH|chiraloh","SOCl2, dioxane","RCl|chiralcl","the byproduct of this reaction,; SO2, is a gas;gives retention of configuration",2,11,0,[[0,0]],[[11,463],[0,0],[0,0]]]
,["2 CH3OH,/,ROH","H2SO4, 140 oC","CH3OCH3","bimolecular dehydration;is limited to specific;industrial applications",2,11,0,[[0,0]],[[14,612],[0,0],[0,0]]]
,["ROCH2R',/,ROR|wade4","excess O2;slow","ROOH,ROOR|wade5","autoxidation of ethers; leads to peroxides",0,11,0,[[0,0]],[[14,615],[0,0],[0,0]]]
,["ROH|r3coh","HI, heat","RI|r3ci","substitution of a protonated alcohol",2,11,1,[[12,438]],[[0,0],[0,0],[0,0]]]
,["ROH|r3coh","HBr, heat","RBr|r3cbr","substitution of a protonated alcohol",2,11,1,[[12,438]],[[11,458],[0,0],[0,0]]]
,["ROH|r3coh","HCl","RCl|r3ccl","substitution of a protonated alcohol",2,11,1,[[12,438]],[[11,459],[0,0],[0,0]]]
,["ROH|r3coh","HCl;ZnCl2","RCl|r3ccl","zinc chloride is better than HCl by itself",2,11,1,[[12,439]],[[11,459],[0,0],[0,0]]]
,["ROH|chiraloh","PBr3;pyridine","RBr|chiralbr","reacts with inversion",2,11,2,[[12,442]],[[11,461],[0,0],[0,0]]]
,["ROH|chiraloh","SOCl2;pyridine","RCl|chircl2","SOCl2 is thionyl chloride##;reacts with inversion",2,11,2,[[12,442]],[[0,0],[0,0],[0,0]]]
,["CH3CH2OH,/,ROH","TsCl;pyridine","CH3CH2OTs,/,ROTs","TsCl is p@-toluenesulfonic acid##;TsO- is an excellent leaving group",0,11,3,[[12,443]],[[11,455],[0,0],[0,0]]]
,["CH3SH,/,RSH,ROTs","1. base;2. CH3CH2OTs","CH3SCH2CH3,/,RSR'","substitution of a tosylate;by RS-",0,11,3,[[12,444]],[[0,0],[0,0],[0,0]]]
,["CH3CH2OTs,/,ROTs","NaCN","CH3CH2CN,/,RCN","forms a C--C bond",0,11,3,[[12,444]],[[11,456],[0,0],[0,0]]]
,["CH3CH2OTs,/,ROTs","X-","CH3CH2X,/,ROR', RX,RF, RCl, RBr, RI, RCN, RSR', alkyne","X = OR', F, Cl, Br, I, CN, acetylide##;in the cases of CN- and acetylide,;this reaction forms a C--C bond",0,11,3,[[12,444]],[[11,456],[0,0],[0,0]]]
,["ROH|c6h9mo","H2SO4 or H3PO4;heat","alkene|c7mix","harsh! Use POCl3 to avoid rearrangements",2,11,4,[[12,445]],[[0,0],[0,0],[0,0]]]
,["CH3CH2OH,/,ROH","1. TsCl, pyridine;2. X-","CH3CH2X,/,ROR', RX,RF, RCl, RBr, RI, RCN, RSR', alkyne","X = OR', F, Cl, Br, I, CN, acetylide##;in the cases of CN- and acetylide,;this reaction forms a C--C bond",0,11,3,[[12,444]],[[11,456],[0,0],[0,0]]]
,["CH3OCH3","HI, heat","CH3I","substitution of a protonated ether",0,11,5,[[12,452]],[[14,613],[0,0],[0,0]]]
,["epoxide,/,ROR', ROH|da22","HX","ROH,/,RCl, RBr|da24","X = Br, OH, OR';acidic conditions lead to;opening at the more substituted carbon",0,11,6,[[12,455]],[[8,345],[14,622],[0,0]]]
,["epoxide,/,ROR', ROH, RNH2, RSH, alkyne|da22","1. X-;2. H2O","ROH,/,RCl, RBr, RI, RCN, RSR', alkyne|da23","general nucleophilic opening of epoxides;occurs at the less substituted position,;possibly forming a C--C bond",0,11,6,[[12,457]],[[14,626],[0,0],[0,0]]]
,["(CH3)2CHSH,/,RSH,RBr","1. base;2. CH3Br","(CH3)2CHSCH3,/,RSH","substitution of an alkyl halide by RS-",0,11,10,[[12,464]],[[14,616],[0,0],[0,0]]]
,["CH3SCH3,/,R2S,RBr, RCl, RI","CH3X","(CH3)3S+X-","X = Br, Cl, I",0,11,10,[[12,464]],[[14,618],[0,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","Li; Et2O or THF","CH3CH2Li","X = Br, Cl, I",0,11,8,[[12,467]],[[10,421],[0,0],[0,0]]]
,["CH3X,/,RBr, RCl, RI","Mg; Et2O or THF","CH3MgBr","X = Br, Cl, I; Grignard reagent",0,11,8,[[12,467]],[[10,421],[0,0],[0,0]]]
,["epoxide,/,RMgBr|da22","R'MgBr","ROH|da25","forms a C--C bond",0,11,8,[[12,468]],[[10,428],[11,629],[0,0]]]
,["CH3CH2MgBr or CH3CH2Li","H2O","CH3CH3","reaction of an organometallic compound;with water give an alkane",0,11,8,[[12,469]],[[10,430],[0,0],[0,0]]]
,["CH3CH2X,/,RBr, RCl, RI","1. Mg;2. H2O","CH3CH3","X = Br, Cl, I",2,11,8,[[12,469]],[[10,430],[0,0],[0,0]]]
,["R2CuLi,/,RX, alkene|da26","R'2CuLi, ether","alkene|da27","forms a C--C bond",0,11,8,[[12,470]],[[0,0],[0,0],[0,0]]]
,["CH3Li","CuI, ether","(CH3)2CuLi","formation of an organocopper reagent",0,11,8,[[12,470]],[[10,430],[0,0],[0,0]]]
,["(CH3)2CuLi,/,RX","CH3CH2X, ether","CH3CH2CH3","forms a C--C bond##;R' should be vinylic or allylic",0,11,8,[[12,470]],[[10,430],[0,0],[0,0]]]
,["R4N+ HO-,/,R4N+X-|da30","heat","alkene|da31","Hofmann elimination##;gives the non@-Zaitsev product",0,11,11,[[21,889]],[[19,862],[0,0],[0,0]]]
,["ArH|benzene","Cl2;AlCl3","ArCl|phcl","chlorination",0,14,0,[[0,0]],[[17,725],[0,0],[0,0]]]
,["R2C=O, RCHO|phac","Zn(Hg), HCl, heat","RH, ArR|phet","Clemmensen reduction",0,14,0,[[0,0]],[[17,749],[18,820],[0,0]]]
,["ArH|benzene","Cl2;FeCl3","ArCl|phcl","chlorination",0,14,9,[[15,608]],[[0,0],[0,0],[0,0]]]
,["ArH|benzene","Br2;FeBr3","ArBr|phbr","bromination",0,14,9,[[15,608]],[[17,723],[0,0],[0,0]]]
,["ArH|benzene","I2, HNO3","ArI|phi","iodination",0,14,9,[[15,609]],[[17,725],[0,0],[0,0]]]
,["ArH|benzene","HNO3;H2SO4","ArNO2|phno2","nitration",0,14,10,[[15,609]],[[17,726],[0,0],[0,0]]]
,["ArH|benzene","H2SO4, heat","ArSO3H|phso3h","sulfonation",0,14,11,[[15,610]],[[17,726],[0,0],[0,0]]]
,["ArSO3H|phso3h","H3O+, heat","benzene|benzene","desulfonation",0,14,11,[[15,610]],[[17,727],[0,0],[0,0]]]
,["ArH|benzene","1. CH3COCl, AlCl3;2. H2O","R2C=O, RCHO|phac","Friedel--Crafts acylation",0,14,12,[[15,612]],[[17,746],[0,0],[0,0]]]
,["ArH|benzene","1. CH3CH2Cl, AlCl3;2. H2O","ArR|phet","Friedel--Crafts alkylation",0,14,13,[[15,613]],[[17,742],[0,0],[0,0]]]
,["R2C=O, RCHO|phac","Zn(Hg), HCl, heat;or;H2NNH2, HO-, heat","RH, ArR|phet","Clemmensen reduction uses Zn(Hg)##;Wolff--Kishner reduction uses hydrazine",0,14,14,[[15,616]],[[17,749],[18,820],[0,0]]]
,["RH|phpr","NBS, peroxide, heat","RBr|phpr2","benzylic bromination,;using N@-bromosuccinimide",0,15,2,[[16,626]],[[17,759],[0,0],[0,0]]]
,["ArH|benzene","H2, Ni;170 oC, 180 atm","RH|c6h12","catalytic hydrogenation of benzene;to give cyclohexane;requires extreme conditions",0,15,2,[[16,627]],[[17,755],[0,0],[0,0]]]
,["RCN|phcn","H2, Ni","RNH2|phmnh2","catalytic hydrogenation of a nitrile;to give a primary amine",0,15,2,[[16,627]],[[21,974],[0,0],[0,0]]]
,["ArH|phet","KMnO4, heat","RCO2H|phco2h","benzylic oxidation;of an alkyl benzene",0,15,2,[[16,627]],[[17,757],[20,919],[0,0]]]
,["ArCHOH|phetoh","Na2Cr2O7, H+, heat","RCO2H|phco2h","benzylic oxidation;of a benzylic alcohol##;harsh conditions",0,15,2,[[16,627]],[[0,0],[0,0],[0,0]]]
,["ArCHOH|phetoh","MnO2, heat","R2C=O|phac","benzylic oxidation;of a benzylic alcohol##;mild conditions",0,15,2,[[16,628]],[[11,450],[0,0],[0,0]]]
,["ArNO2|phno2b","(NH4)2S","RNH2, ArNH2|phnh2b","selective reduction;of one nitro group;by ammonium sulfide",0,15,2,[[16,629]],[[0,0],[0,0],[0,0]]]
,["ArNO2|phno2","H2, Pd/C;or;1. Sn, HCl;2. HO-","RNH2, ArNH2|phnh2","catalytic hydrogenation;of an aromatic nitrate to an aniline",0,15,2,[[16,629]],[[19,884],[0,0],[0,0]]]
,["ArNH2|phnh2","HNO2, HCl;0 oC","ArN2|phn2","formation of an arenediazonium salt;from an aniline",0,15,10,[[16,646]],[[19,868],[0,0],[0,0]]]
,["ArN2|phn2","CuBr","ArBr|phbr","reaction of an arenediazonium salt;with copper(I) bromide;( Sandmeyer reaction )",0,15,10,[[16,647]],[[19,870],[0,0],[0,0]]]
,["ArN2|phn2","CuCl","ArCl|phcl","reaction of an arenediazonium salt;with copper(I) chloride;( Sandmeyer reaction )",0,15,10,[[16,647]],[[19,870],[0,0],[0,0]]]
,["ArN2|phn2","CuCN","ArCN|phcn","reaction of an arenediazonium salt;with copper(I) cyanide;( Sandmeyer reaction )",0,15,10,[[16,647]],[[19,870],[0,0],[0,0]]]
,["ArN2|phn2","KI","ArI|phi","reaction of an arenediazonium salt;with potasium iodide",0,15,10,[[16,648]],[[19,870],[0,0],[0,0]]]
,["ArN2|phn2","HBF4, heat","ArF|phf","reaction of an arenediazonium salt;with fluoroboric acid;( Schiemann reaction )",0,15,10,[[16,648]],[[19,870],[0,0],[0,0]]]
,["ArN2|phn2","H2O","ArOH|phoh","reaction of an arenediazonium salt;with water",0,15,10,[[16,648]],[[19,870],[0,0],[0,0]]]
,["ArN2|phn2","H3PO2","ArH|benzene","reaction of an arenediazonium salt;with hypophosphorous acid",0,15,10,[[16,648]],[[19,870],[0,0],[0,0]]]
,["ArN2, ArOH|phn2","|phoh","ArN2Ar|phn2r2","reaction of an arenediazonium salt;with phenol;to form an azo compound",0,15,11,[[16,650]],[[19,873],[0,0],[0,0]]]
,["ArCl|phcl","NaNH2, NH3(liq)","ArNH2|phnh2","benzyne reaction with amide anion",0,15,14,[[16,655]],[[0,0],[0,0],[0,0]]]
,["ArBr|phbr","|furanr","|benzynep","benzyne reaction with furan;is an example of a Diels--Alder reaction",0,15,14,[[16,656]],[[0,0],[0,0],[0,0]]]
,["RCO2R|rcoor2","1. CH3MgBr;2. H+, H2O","ROH|romm","Grignard addition;adds twice, to give a tertiary alcohol",0,16,0,[[0,0]],[[10,426],[21,975],[0,0]]]
,["acyl halide, acyl chloride|rcocl","1. CH3MgBr;2. H+, H2O","ROH|romm","Grignard addition;adds twice, to give a tertiary alcohol",0,16,0,[[0,0]],[[10,426],[21,975],[0,0]]]
,["CH3CH2CN,/,RCN","1. CH3MgBr;2. H+, H2O","R2C=O|wade8","Grignard addition;to a nitrile;gives a ketone",0,16,0,[[0,0]],[[18,793],[21,976],[0,0]]]
,["acyl halide, acyl chloride|rcocl","(CH3)2CuLi","R2C=O|wade9","lithium dialkyl cuprate;gives the ketone",0,16,0,[[0,0]],[[18,794],[0,0],[0,0]]]
,["amide|rconh2","Cl2 or Br2, NaOH","RNH2","Hofmann rearrangement",0,16,0,[[0,0]],[[19,885],[0,0],[0,0]]]
,["RCO2H|rco2h","CH2N2","RCO2R|rco2m","esterification using;diazomethane",0,16,0,[[0,0]],[[20,928],[0,0],[0,0]]]
,["acyl halide,RNH2|rcox","CH3NH2/pyridine ;or; 2 CH3NH2","amide|rconhm","nucleophilic acyl substitution",0,16,7,[[17,686]],[[19,859],[20,927],[21,960]]]
,["acyl halide,ROH|rcox","CH3OH","RCO2R|rco2m","nucleophilic acyl substitution",0,16,7,[[17,686]],[[20,926],[21,960],[0,0]]]
,["acyl halide|rcox","CH3CO2Na","acid anhydride|rcoocom","nucleophilic acyl substitution",0,16,7,[[17,686]],[[21,959],[0,0],[0,0]]]
,["acyl halide,RCO2H|rcox","CH3CO2H","acid anhydride|rcoocom","nucleophilic acyl substitution",0,16,7,[[17,686]],[[21,959],[0,0],[0,0]]]
,["acyl halide|rcox","H2O","RCO2H|rco2h","nucleophilic acyl substitution",0,16,7,[[17,686]],[[21,968],[0,0],[0,0]]]
,["acid anhydride,ROH|rcoocor","CH3OH","RCO2R|rco2m","nucleophilic acyl substitution",0,16,8,[[17,689]],[[21,960],[0,0],[0,0]]]
,["acid anhydride,RNH2|rcoocor","CH3NH2/pyridine ;or; 2 CH3NH2","amide|rconhm","nucleophilic acyl substitution",0,16,8,[[17,689]],[[21,960],[0,0],[0,0]]]
,["acid anhydride|rcoocor","H2O","RCO2H|rco2h","nucleophilic acyl substitution",0,16,8,[[17,689]],[[21,968],[0,0],[0,0]]]
,["RCO2R,ROH|rcoor2","CH3OH; H+ or CH3O-","RCO2R|rco2m","transesterification",0,16,9,[[17,690]],[[21,961],[0,0],[0,0]]]
,["RCO2R,RNH2|rcoor2","CH3NH2","amide|rconhm","nucleophilic acyl substitution",0,16,9,[[17,690]],[[21,961],[0,0],[0,0]]]
,["RCO2R|rcoor2","H+, H2O or HO-, H2O ","RCO2H|rco2h","hydrolysis of an ester",0,16,9,[[17,691]],[[21,968],[0,0],[0,0]]]
,["RCO2H,ROH|rco2h","CH3OH, H+, H2O ;or; 1. HO-/H2O;2. CH3Br","RCO2R|rco2m","acid method is Fischer esterification",0,16,12,[[17,702]],[[11,474],[20,922],[21,965]]]
,["RCO2H|rco2h","CH3NH2;heat above 200 oC","amide|rconhm","decomposition of an ammonium salt;of a carboxylic acid",0,16,12,[[17,703]],[[20,929],[0,0],[0,0]]]
,["amide|rconh2","H+, H2O ;or; HO-, H2O;heat","RCO2H|rco2h","hydrolysis of an amide",0,16,13,[[17,704]],[[21,970],[0,0],[0,0]]]
,["amide|rconh2","P2O5, heat","RCN","dehydration of a primary amide;to give a nitrile",0,16,13,[[17,704]],[[21,985],[0,0],[0,0]]]
,["RBr","phthalamide|gabrial","RNH2","Gabriel synthesis of an amine",0,16,15,[[17,708]],[[19,881],[0,0],[0,0]]]
,["RCN","H+, H2O;heat","RCO2H|rco2h","hydrolysis of a nitrile",0,16,16,[[17,709]],[[20,919],[21,971],[0,0]]]
,["CH3CH2Br,/,RBr, RCl","1. NaCN;2. H+, H2O","CH3CH2CO2H,/,RCO2H|rco2h","conversion of an alkyl halide;to a carboxylic acid;via a nitrile",0,16,16,[[17,709]],[[20,919],[0,0],[0,0]]]
,["RCO2H|rco2h","PBr3","acyl halide|rcobr","formation of an acyl bromide;from a carboxylic acid",0,16,18,[[17,712]],[[0,0],[0,0],[0,0]]]
,["RCO2H|rco2h","SOCl2 or PCl3","acyl halide, acyl chloride|rcocl","formation of an acyl chloride;from a carboxylic acid",0,16,18,[[17,712]],[[18,794],[20,926],[21,976]]]
,["RCO2H|rco2h","P2O5","acid anhydride|rcoocor","dehydration",0,16,18,[[17,713]],[[0,0],[0,0],[0,0]]]
,["RCO2H|succinic","heat","acid anhydride|rcoocor2","dicarboxylic acid dehydration",0,16,19,[[17,717]],[[21,979],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. CH3NH2;2. LiAlH4","R2NH|rrchnhm","aldehyde or ketone;reductive amination",0,17,0,[[0,0]],[[19,878],[0,0],[0,0]]]
,["RCO2H|rco2h","1. 2 eq. CH3Li;2. H+, H2O","R2C=O|wade9","two equivalents;are needed",0,17,0,[[0,0]],[[20,931],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. CH3MgBr;2. H+, H2O","ROH|romr2","the reaction of an aldehyde or a ketone;with a Grignard reagent;gives an alcohol",0,17,4,[[18,738]],[[10,424],[18,798],[0,0]]]
,["CO2","1. CH3MgBr;2. H+, H2O","RCO2H|mcooh","the reaction of carbon dioxide;with a Grignard reagent;gives an acid",0,17,4,[[18,739]],[[20,919],[0,0],[0,0]]]
,["CH3X,/,RBr, RCl","1. Mg;2. CO2;3. H+, H2O","RCO2H|mcooh","the reaction of carbon dioxide;with a Grignard reagent;gives an acid",0,17,4,[[18,739]],[[20,919],[0,0],[0,0]]]
,["RCO2R|rcoor2","1. CH3MgBr;2. H+, H2O","ROH|romm","Grignard addition;adds twice, to give a tertiary alcohol",0,17,6,[[18,740]],[[10,426],[21,975],[0,0]]]
,["acyl halide, acyl chloride|rcocl","1. CH3MgBr;2. H+, H2O","ROH|romm","Grignard addition;adds twice, to give a tertiary alcohol",0,17,6,[[18,740]],[[10,426],[21,975],[0,0]]]
,["R2C=O, RCHO|rcor2","acetylide|acetr","ROH, alkyne|r2oac","the reaction of an aldehyde or a ketone;with an acetylide;gives an alkyne",0,17,4,[[18,741]],[[9,379],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","NaCN, HCl","ROH, RCN|r2ocn","the reaction of an aldehyde or a ketone;with cyanide;gives a nitrile",0,17,4,[[18,741]],[[18,806],[0,0],[0,0]]]
,["RCN","H2/Pt","RNH2|rch2nh2","hydrogenation of a nitrile;gives a primary amine",0,17,4,[[18,742]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. NaCN, HCl;2. H+, H2O","ROH, RCO2H|r2ocacid","synthesis of an alpha@-hydroxy acid;from a ketone or an aldehyde",0,17,4,[[18,742]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. NaCN, HCl;2. H2/Pt","ROH, RNH2|r2ocamin","synthesis of a beta@-hydroxy amine;from a ketone or an aldehyde",0,17,4,[[18,742]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. NaBH4 or LiAlH4;2. H+, H2O","ROH|rchro","hydride reduction",0,17,5,[[18,743]],[[10,433],[18,798],[0,0]]]
,["RCO2R|rcoor2","1. LiAlH4;2. H2O","ROH|rch2o","hydride reduction",0,17,6,[[18,743]],[[10,433],[21,973],[0,0]]]
,["RCO2R|rcoor2","1. (iso@-Bu)2AlH, --78 oC;2. H2O","RCHO|rcho","hydride reduction with; diisobutylaluminum hydride",0,17,6,[[18,744]],[[0,0],[0,0],[0,0]]]
,["RCO2H|rco2h","1. LiAlH4;2. H3O+","ROH|rch2o","hydride reduction",0,17,6,[[18,745]],[[10,433],[0,0],[0,0]]]
,["acyl halide, acyl chloride|rcocl","1. LiAlH4;2. H3O+","ROH|rch2o","hydride reduction",0,17,6,[[18,745]],[[10,433],[21,973],[0,0]]]
,["acyl halide, acyl chloride|rcocl","1. Li(tert@-BuO)3AlH, --78 oC;2. H2O","RCHO|rcho","hydride reduction with lithium; tri@-tert@-butoxyaluminum hydride",0,17,6,[[0,0]],[[18,794],[20,930],[21,973]]]
,["amide|rconh2","1. LiAlH4;2. H2O","RNH2|rch2nh2","hydride reduction",0,17,6,[[18,746]],[[19,880],[21,974],[0,0]]]
,["amide|rconhr","1. LiAlH4;2. H2O","R2NH|rch2nhr","hydride reduction",0,17,6,[[18,746]],[[21,974],[0,0],[0,0]]]
,["amide|rconr2","1. LiAlH4;2. H2O","R3N|rch2nr2","hydride reduction",0,17,6,[[18,746]],[[21,974],[0,0],[0,0]]]
,["R2C=O, RCHO|rrco","CH3NH2,/,RNH2==","imine|r2cnm","the reaction of an aldehyde or a ketone;with a primary amine;gives a Schiff base imine",0,17,7,[[18,748]],[[18,807],[0,0],[0,0]]]
,["R2C=O, RCHO|rrco","H2NOH==","oxime|r2cnoh","the reaction of an aldehyde or a ketone;with hydroxylamine;gives an oxime",0,17,7,[[18,751]],[[18,810],[0,0],[0,0]]]
,["R2C=O, RCHO|rrco","H2NNH2==","hydrazone|r2cnn","the reaction of an aldehyde or a ketone;with hydrazine;gives a hydrazone",0,17,7,[[18,751]],[[18,810],[0,0],[0,0]]]
,["R2C=O, RCHO|rrco","H2NNHCONH2==","semicarbazide|r2cncarb","the reaction of an aldehyde or a ketone;with semicarbazide;gives a semicarbazone ",0,17,7,[[18,751]],[[18,810],[0,0],[0,0]]]
,["R2C=O, RCHO|rcoha","(CH3)2NH==","enamine|enamine","the reaction of an aldehyde or a ketone;with a secondary amine;gives an enamine",0,17,7,[[18,751]],[[22,1015],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. NH3;2. NaBH(OAc)3","RNH2|rrchn","aldehyde or ketone;reductive amination",0,17,7,[[18,752]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","H2NNH2, HO-, heat","RH|rch2r2","aldehyde or ketone;Wolff--Kishner reduction",0,17,7,[[18,752]],[[18,820],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","H2O, H+==","ROH|hydrate","aldehyde or ketone##;reversible formation of a hydrate",0,17,8,[[18,753]],[[18,804],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","CH3OH, H+==","ROR|ketal","aldehyde or ketone##;reversible formation of an acetal or a ketal protecting group",0,17,8,[[18,756]],[[18,812],[0,0],[0,0]]]
,["ROR|ketal","H2O, H+==","R2C=O, RCHO|rcor2","aldehyde or ketone##;removal of an acetal or a ketal protecting group",0,17,9,[[18,756]],[[18,814],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","HSCH2CH2CH2SH, H+==","RSR|sketal","aldehyde or ketone##;reversible formation of a thioacetal or thioketal;for reduction to an alkane",0,17,9,[[18,761]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. RSH, H+;2. H2/Raney Ni","RH|rch2r2","aldehyde or ketone##;reduction to an alkane;via a thioacetal or thioketal##;alternative to Wolff--Kishner reduction",0,17,10,[[18,761]],[[0,0],[0,0],[0,0]]]
,["RSR|sketal","H2/Raney Ni","RH|rch2r2","reduction of a thioacetal or thioketal;to an alkane",0,17,10,[[18,761]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","phosphonium ylide|wittigr","alkene|wittigp","Wittig reaction",0,17,11,[[18,761]],[[18,800],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","NaCN","R2C=O, RCN|14ketopi","conjugate addition ( @1,@4@-addition );of a weakly basic nucleophile",0,17,14,[[18,770]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","CH3NH2,/,RNH2","R2C=O, R2NH|14ketopn","conjugate addition ( @1,@4@-addition );of a weakly basic nucleophile",0,17,14,[[18,770]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","CH3SH,/,RSH","R2C=O, RSR|14ketops","conjugate addition ( @1,@4@-addition );of a weakly basic nucleophile",0,17,14,[[18,770]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","HBr","R2C=O, RBr|14ketopb","conjugate addition ( @1,@4@-addition );of a weakly basic nucleophile",0,17,14,[[18,770]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","CH3Li or CH3MgBr","ROH, alkene|12ketopc","direct addition ( @1,@2@-addition );of a strongly basic nucleophile",0,17,14,[[18,771]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","NaBH4 or LiAlH4","ROH, alkene|12ketoph","direct addition ( @1,@2@-addition );of a strongly basic nucleophile",0,17,14,[[18,771]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|12ketone","(CH3)2CuLi","R2C=O|14ketopc","conjugate addition ( @1,@4@-addition );of a weakly basic nucleophile;( Gilman reagent )",0,17,14,[[18,771]],[[22,1043],[0,0],[0,0]]]
,["RCO2R|12ester","HBr","RCO2R, RBr|14esterp","conjugate addition ( @1,@4@-addition ) to an ester;of a weakly basic nucleophile",0,17,15,[[18,772]],[[0,0],[0,0],[0,0]]]
,["RCO2R|12ester","1. HO-, H2O;2. H+, H2O","RCO2H, alkene|12acid","direct addition ( @1,@2@-addition ) to an ester;of a strongly basic nucleophile;leads to acyl substitution",0,17,15,[[0,0]],[[0,0],[0,0],[0,0]]]
,["R2C=O|c6dione","H+ or HO-==","|c6enol","keto--enol equilibrium;especially with @1,@3@-dioxo compounds",-1,19,2,[[19,792]],[[0,0],[0,0],[0,0]]]
,["RH, RCO2R|phac","I2, H+, H2O","RI, RCO2R|phaci","alpha@-halogenation;acidic conditions",0,19,4,[[19,795]],[[0,0],[0,0],[0,0]]]
,["RH, RCHO|ch19a","Br2, HO-","RBr, RCHO|ch19c","alpha@-halogenation;basic conditions;exhaustive",0,19,4,[[19,795]],[[22,1007],[0,0],[0,0]]]
,["RH, RCHO|ch19a","Br2, H+, H2O","RBr, RCHO|ch19b","alpha@-halogenation;acidic conditions",0,19,4,[[0,0]],[[22,1011],[0,0],[0,0]]]
,["RCl, R2C=O|c6h10o","Cl2, H+, H2O","RCl, R2C=O|c6h9ocl","alpha@-halogenation;acidic conditions",0,19,4,[[19,795]],[[22,1011],[0,0],[0,0]]]
,["RH, R2C=O|phac","I2, HO-","RCO2H|phco2h","alpha@-halogenation;basic conditions;( haloform reaction )",0,19,4,[[19,796]],[[22,1009],[0,0],[0,0]]]
,["RBr|c6h9obr","X-","R2C=O, RX,/,ROR', RCN, RSR', alkyne|c6h9ox","S_N@2 reaction;X = OR', SR', CN, acetylide##;reaction with CN- or acetylide forms a C--C bond",0,19,6,[[19,797]],[[0,0],[0,0],[0,0]]]
,["RCO2H|ch19d","1. PBr3 (or P), Br2;2. H2O","RBr, RCO2H|ch19e","alpha@-bromination of a carboxylic acid;( Hell--Vollhard--Zelinski reaction )",0,19,5,[[19,797]],[[22,1012],[0,0],[0,0]]]
,["RBr|c6h9obr","tert@-BuO-;tert@-BuOH","R2C=O, alkene|c6h8o","E@2 elimination;of alpha@-halo carbonyl compound;allows introduction of groups;at the beta@-position",0,19,6,[[19,798]],[[0,0],[0,0],[0,0]]]
,["R2C=O|c6h10o","1. LDA, THF;2. CH3I","R2C=O|ch19f","alkylation of an enolate;forms a C--C bond;( not very selective )",0,19,8,[[19,799]],[[22,1014],[0,0],[0,0]]]
,["hydrazone, R2C=O|c6h9om","|hydrazr","R2C=O|c6h8om2","alkylation of a deprotonated hydrazone;solves a regiochemical problem",0,19,8,[[19,800]],[[0,0],[0,0],[0,0]]]
,["enamine, R2C=O|enamine1","1. CH3I;2. H2O","R2C=O|c5h7om","use of an enamine;avoids multiple alkylation",0,19,9,[[19,802]],[[22,1016],[0,0],[0,0]]]
,["enamine, R2C=O, RI|c5h8o","|enaminer","R2C=O|c5h7om","pyrrolidine enamine;avoids multiple alkylation",2,19,9,[[19,803]],[[22,1016],[0,0],[0,0]]]
,["enamine, R2C=O, RCOC,acyl halidel|c6h10o","|enaminr2","R2C=O|c6h9oac","pyrrolidine enamine;allows acylation",2,19,9,[[19,803]],[[22,1017],[0,0],[0,0]]]
,["R2C=O|c6h8o","|michael1","R2C=O|ch19g","Michael addition",0,19,10,[[19,804]],[[22,1042],[0,0],[0,0]]]
,["enamine, R2C=O, RCHO|enamine2","|enaminr3","R2C=O|ch19h","Stork enamine reaction;is a Michael addition",0,19,10,[[19,805]],[[22,1043],[0,0],[0,0]]]
,["RCHO|aldol1","HO-","RCHO, R2C=O, ROH|aldol2","aldol addition",0,19,10,[[19,806]],[[22,1017],[0,0],[0,0]]]
,["R2C=O|aldol3","HO-","R2C=O, ROH|aldol4","aldol addition",0,19,10,[[19,806]],[[22,1017],[0,0],[0,0]]]
,["R2C=O|aldol3","H+ or HO-","R2C=O, alkene|aldol5","aldol condensation",0,19,11,[[19,807]],[[22,1017],[0,0],[0,0]]]
,["R2C=O, ROH|aldol4","H+ or HO-","R2C=O, alkene|aldol5","aldol condensation",0,19,11,[[19,807]],[[22,1020],[0,0],[0,0]]]
,["R2C=O, RCHO|aldol7","HO-","R2C=O, alkene|aldol6","mixed (or crossed) aldol condensation;is practical only when;one substrate;has no alpha@-hydrogens",0,19,13,[[19,808]],[[22,1021],[0,0],[0,0]]]
,["RCO2R|clais1","1. CH3CH2O-;2. H+","R2C=O, RCO2R|clais2","Claisen condensation;requires two equivalents of base,;which must be from the same alcohol as the ester",0,19,14,[[19,810]],[[22,1027],[0,0],[0,0]]]
,["R2C=O, RCO2R, RCHO|clais3","1. CH3CH2O-;2. H+","R2C=O, RCO2R, RCHO|c6h9of","mixed (or crossed) Claisen condensation;requires excess ester",0,19,15,[[19,812]],[[22,1031],[0,0],[0,0]]]
,["R2C=O, RCO2R|clais5","1. CH3CH2O-;2. H+","R2C=O, RCO2R|c6h9oest","mixed (or crossed) Claisen condensation;works also with carbonates",0,19,15,[[19,813]],[[0,0],[0,0],[0,0]]]
,["RCO2R|clais4","1. CH3CH2O-;2. H+","R2C=O, RCO2R|c6h9oac","intramolecular Claisen;is the Dieckmann condensation",0,19,16,[[19,814]],[[22,1031],[0,0],[0,0]]]
,["R2C=O|aldol8","HO-","R2C=O, ROH|aldol9","intramolecular aldol addition",0,19,16,[[19,815]],[[22,1025],[0,0],[0,0]]]
,["R2C=O|aldol8","1. HO-;2. H+","R2C=O, alkene|c6h8o","intramolecular aldol condensation",0,19,16,[[0,0]],[[22,1025],[0,0],[0,0]]]
,["R2C=O, alkene|robin1","HO-, heat","R2C=O, alkene|robin2","Robinson annulation;is Michael addition;followed by aldol condensation",0,19,16,[[19,817]],[[22,1046],[0,0],[0,0]]]
,["RCO2H, R2C=O|c6h9oacd","heat","R2C=O|c6h10o","decarboxylation of a beta@-ketocarboxylic acid",0,19,17,[[19,819]],[[22,1040],[0,0],[0,0]]]
,["RBr, RCO2R|malester","|malonr","RCO2H|malon3","malonic ester synthesis;adds CH2CO2H;to an alkyl bromide",0,19,18,[[19,821]],[[22,1036],[0,0],[0,0]]]
,["RCO2R, R2C=O|c6h9oest","H+, heat","R2C=O|c6h10o","decarboxylation of a beta@-ketoester##;first a hydrolysis to the acid,;then decarboxylation",0,19,18,[[19,821]],[[22,1040],[0,0],[0,0]]]
,["RBr, R2C=O|acacest","|acacr","R2C=O|acac2","acetoacetic ester synthesis;adds CH2COCH3;to an alkyl bromide",0,19,19,[[19,822]],[[22,1040],[0,0],[0,0]]]
,["alkene|styrene","H2, Pd/C","RH|phet","selective hydrogenation of an alkene;in the presence of an aromatic ring",0,18,1,[[20,845]],[[0,0],[0,0],[0,0]]]
,["acyl halide, acyl chloride|rcocl","H2, Pd/C","ROH|rch2o","hydrogenation of an acyl halide",0,18,1,[[0,0]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rrco","H2; Pd/C or Raney Ni","ROH|rchro","hydrogenation of a ketone or an aldehyde to an alcohol",0,18,1,[[20,845]],[[10,434],[0,0],[0,0]]]
,["imine|r2cnm","H2, Pd/C","R2NH|iminep","hydrogenation of a Schiff base imine to a secondary amine",0,18,1,[[20,845]],[[19,878],[0,0],[0,0]]]
,["acyl halide, acyl chloride|rcocl","H2, partially deactivated Pd","RCHO|rcho","hydrogenation of an acyl halide;to an aldehyde;( Rosenmund reduction )",0,18,1,[[20,845]],[[0,0],[0,0],[0,0]]]
,["alkyne|enyne","Na or Li;NH3(liq)","alkene|diene","selective dissolving metal reduction;of an alkyne;in the presence of an alkene",0,18,1,[[20,846]],[[0,0],[0,0],[0,0]]]
,["R2C=O|oxoestr","NaBH4","ROH|ohester","selective hydride reduction of a ketone;in the presence of an ester",0,18,1,[[20,848]],[[0,0],[0,0],[0,0]]]
,["R2C=O|2enone","NaBH4","ROH|2enol","selective hydride reduction of a ketone;in the presence of an alkene",0,18,1,[[20,848]],[[0,0],[0,0],[0,0]]]
,["RCHO|3oxoal","NaBH4; isopropl alcohol","ROH|3oxool","selective hydride reduction of an aldehyde; in the presence of a ketone",0,18,1,[[20,848]],[[0,0],[0,0],[0,0]]]
,["R2C=O|3oxoal","NaBH4, CeCl3;C2H5OH/H2O;--15 oC","ROH|3olal","selective hydride reduction of a ketone; in the presence of an aldehyde",0,18,1,[[20,849]],[[0,0],[0,0],[0,0]]]
,["ROH|cro3a","CrO3, H2SO4;or;Na2Cr2O7, H2SO4,;or;H2CrO4","R2C=O|cro3b","oxidation of a secondary alcohol;to a ketone, using chromium(VI)",0,18,2,[[20,850]],[[11,447],[0,0],[0,0]]]
,["ROH|cro3c","CrO3, H2SO4;or;Na2Cr2O7, H2SO4,;or;H2CrO4","RCO2H|cro3d","oxidation of a primary alcohol;to a carboxylic acid,; using chromium(VI)",0,18,2,[[20,850]],[[11,448],[20,918],[0,0]]]
,["ROH|cro3c","PCC;or;DMSO, (COCl)2, triethylamine","RCHO|cro3e","oxidation of a primary alcohol;to an aldehyde,; using pyridinium chlorochromate;or DMSO/oxalyl chloride ( Swern oxidation )",0,18,2,[[20,851]],[[11,449],[0,0],[0,0]]]
,["R2C=O|cymket","peroxyacid|mcpba","RCO2R|choketm","Baeyer--Villiger oxidation",0,18,3,[[20,853]],[[0,0],[0,0],[0,0]]]
,["CH3CH2CHO,/,RCHO","CrO3, H2SO4;or;Na2Cr2O7, H2SO4;or;H2CrO4;or;Ag2O, NH3","CH3CH2CO2H,/,RCO2H","oxidation of an aldehyde;to a carboxylic acid,; using chromium(VI) or silver(I) ( Tollens' reagent is Ag+/NH3 )",0,18,3,[[20,853]],[[18,820],[0,0],[0,0]]]
,["alkene|limon","peroxyacid|mcpba","epoxide|limon2","selective epoxidation of the more;substituted alkene;in a Baeyer--Villiger oxidation",0,18,4,[[20,854]],[[0,0],[0,0],[0,0]]]
,["alkene|cbutene","peroxyacid|mcpba","epoxide|cbuten2","epoxidation is stereospecific",0,18,4,[[20,855]],[[8,344],[14,619],[0,0]]]
,["alkene|tbutene","peroxyacid|mcpba","epoxide|tbuten2","epoxidation is stereospecific",0,18,4,[[20,855]],[[8,344],[14,619],[0,0]]]
,["alkene|tbutene","OsO4;or;KMnO4, HO-, cold","ROH, diol|butdiol","the formation of a diol from an alkene;is stereospecific",0,18,5,[[20,858]],[[8,347],[0,0],[0,0]]]
,["ROH, diol|butdiol","HIO4","R2C=O|oxcleav","oxidative cleavage of a diol,; using periodic acid",0,18,6,[[20,860]],[[11,473],[0,0],[0,0]]]
,["alkene|tbutene","1. O3, --78 oC;2. H2O2;or;KMnO4, HO-","R2C=O, RCO2H|oxcleav2","oxidative cleavage on an alkene,; using ozone;and an oxidative work@-up",0,18,7,[[20,862]],[[8,349],[20,918],[0,0]]]
,["alkene|tbutene","1. O3, --78 oC;2. Zn or (CH3)2S","R2C=O|oxcleav","oxidative cleavage on an alkene,; using ozone;and a reductive work@-up",0,18,7,[[20,862]],[[8,350],[0,0],[0,0]]]
,["alkene|1butene","1. O3, --78 oC;2. H2O2;or;KMnO4","RCO2H|ozoneox","ozone oxidation followed by;oxidative work@-up",0,18,7,[[20,862]],[[8,349],[0,0],[0,0]]]
,["alkene|1butene","1. O3, --78 oC;2. Zn or (CH3)2S","R2C=O, RCHO|ozonered","ozone oxidation followed by;reductive work@-up",0,18,7,[[20,862]],[[8,350],[0,0],[0,0]]]
,["alkene|1butenem","1. O3, --78 oC;2. H2O2;or;KMnO4, HO-","RCO2H|ozoneox2","potassium permanganate oxidation;is similar to ozone with an oxidative work@-up",0,18,7,[[20,864]],[[8,352],[0,0],[0,0]]]
,["alkyne|2pentyne","KMnO4, HO-","R2C=O|dione","permanganate oxidation of an alkyne;gives a @1,@2@-dione",0,18,8,[[20,866]],[[0,0],[0,0],[0,0]]]
,["alkyne|1butyne","1. O3, --78 oC;2. H2O","RCO2H|ozoneox","ozone oxidation of an alkyne;gives acids;even without an oxidative work@-up",0,18,8,[[20,866]],[[9,395],[0,0],[0,0]]]
,["ROH|quinol","(KSO3)2NO","R2C=O|quinone","oxidation of hydroquinone;to benzoquinone,; using Fremy's salt",0,18,11,[[20,870]],[[0,0],[0,0],[0,0]]]
,["R2C=O|quinone","NaBH4","ROH|quinol","reduction of benzoquinone;to hydroquinone",0,18,11,[[20,870]],[[0,0],[0,0],[0,0]]]
,["RNH2,/,RI","excess CH3I, K2CO3","RN(CH3)3+I-","for Hofmann elimination",0,11,11,[[21,891]],[[19,862],[0,0],[0,0]]]
,["CH3CH2CH2CH2NH2,/,RNH2, R2NH","1. excess CH3I, K2CO3;2. Ag2O, H2O;3. heat","alkene|wade2","Hofmann elimination",0,11,11,[[21,891]],[[19,862],[0,0],[0,0]]]
,["RN(CH3)3+ I-","Ag2O, H2O","RN(CH3)3+ HO-","for Hofmann elimination",0,11,11,[[21,891]],[[19,862],[0,0],[0,0]]]
,["R3N, R3NO|da28","1. H2O2;2. heat","R3NO, alkene|da29","Cope elimination",0,11,11,[[21,894]],[[19,866],[0,0],[0,0]]]
,["CH3CH2Br","NaCN, R4N+HSO4-","CH3CH2CN","formation of a C--C bond,;using phase transfer catalysis",0,11,12,[[21,894]],[[19,848],[0,0],[0,0]]]
,["(CH3)3N","H2O2","(CH3)3NO","forms an amine oxide",0,11,11,[[21,894]],[[19,866],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. NH3;2. H2/Pd or Raney Ni","RNH2|rrchn","aldehyde or ketone;reductive amination",0,17,7,[[21,896]],[[19,877],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. CH3NH2;2. NaBH(OAc)3","R2NH|rrchnhm","aldehyde or ketone;reductive amination",0,17,7,[[21,897]],[[0,0],[0,0],[0,0]]]
,["R2C=O, RCHO|rcor2","1. (CH3)2NH;2. NaBH(OAc)3","R3N|rrchnm2","aldehyde or ketone;reductive amination",0,17,7,[[21,897]],[[19,878],[0,0],[0,0]]]
,["RCHO|c_mann","1. NaBH4;2. H+, H2O;or;H2, Pd/C","ROH|c_mannoh","reduction of an aldose;to an alditol",0,20,5,[[22,927]],[[23,1072],[0,0],[0,0]]]
,["R2C=O|c_fruc","1. NaBH4;2. H+, H2O;or;H2, Pd/C","ROH|c_frucoh","reduction of a ketose;gives a mixture of alditols",0,20,5,[[22,927]],[[23,1072],[0,0],[0,0]]]
,["RCHO|c_gluc","Br2, H2O","RCO2H|c_glucon","oxidation of an aldose;to an aldonic acid",0,20,5,[[22,928]],[[23,1074],[0,0],[0,0]]]
,["RCHO|c_gluc","Ag(NH3)2+ -OH","RCO2H|c_glucon","Tollens reagent",0,20,5,[[22,928]],[[23,1074],[0,0],[0,0]]]
,["RCHO, R2C=O|c_fruc","HO-, H2O==","RCHO, R2C=O|c_fruceq","base@-catalyzed equilibrium;between a ketose and two possible aldoses",0,20,5,[[22,928]],[[23,1071],[0,0],[0,0]]]
,["RCHO|c_gluc","HNO3, heat","RCO2H|c_glucar","oxidation of an aldose;to an aldaric acid",0,20,5,[[22,929]],[[23,1074],[0,0],[0,0]]]
,["RCHO|c_gluc","3 H2NNHC6H5","|c_osazon","formation of an osazone;from an aldose",0,20,6,[[22,930]],[[23,1080],[0,0],[0,0]]]
,["R2C=O|c_fruc","3 H2NNHC6H5","|c_osazon","formation of an osazone;from a ketose",0,20,6,[[22,930]],[[23,1080],[0,0],[0,0]]]
,["RCHO|c_eryt","NaCN, HCl","RCN|c_cyan12","formation of a cyanohydrin;from an aldose",0,20,7,[[22,931]],[[23,1082],[0,0],[0,0]]]
,["RCN|c_cyan1","1. H2, Pd/BaSO4;2. H+, H2O","RCHO|c_ribo","formation of an aldose;from a cyanohydrin",0,20,7,[[22,931]],[[23,1082],[0,0],[0,0]]]
,["RCHO|c_eryt","1. NaCN, HCl;2. H2, Pd/BaSO4;3. H+, H2O","RCHO|c_cyan12","chain elongation;( Kiliani--Fischer synthesis )",0,20,7,[[22,931]],[[23,1082],[0,0],[0,0]]]
,["RCO2H|c_ruff1","H2O2, Fe^3+","RCHO|c_arab","chain shortening;( Ruff degradation )",0,20,8,[[22,932]],[[23,1081],[0,0],[0,0]]]
,["RCHO|c_gluc","1. Br2, H2O;2. Ca(OH)2;3. H2O2, Fe^3+","RCHO|c_arab","chain shortening;( Ruff degradation )",0,20,8,[[22,932]],[[23,1081],[0,0],[0,0]]]
,["RCHO|c_gluc","H+, H2O==","RCHO|c_glucab","acid@-catalyzed aldose equilibrium;with pyranoses",0,20,10,[[22,935]],[[23,1068],[0,0],[0,0]]]
,["RCHO, acid anhydride|c_glucb","|c_gluca1","RCO2R|c_glucac","acylation;of a monosaccharide",0,20,12,[[22,939]],[[23,1079],[0,0],[0,0]]]
,["RCHO, RX|c_glucb","excess CH3I;Ag2O","ROR|c_glucam","alkylation;of a monosaccharide",0,20,12,[[22,939]],[[23,1088],[0,0],[0,0]]]
,["RCHO, RX|c_gluc","CH3CH2OH, H+","ROR|c_glucid","acid@-catalyzed;formation of a glycoside",0,20,13,[[22,939]],[[23,1076],[0,0],[0,0]]]
,["RCHO, RNH2|c_ribo","|c_ribo1","R2NH|c_ribon","acid@-catalyzed;formation of an N@-glycoside",0,20,13,[[22,940]],[[0,0],[0,0],[0,0]]]
,["ROR|c_glucam","H+, H2O","ROR|c_glucme","acid@-catalyzed;opening of a glycoside",0,20,16,[[22,942]],[[23,1089],[0,0],[0,0]]]
,["ROR|c_gluci2","1. HIO4;2. H+, H2O","RCHO|c_glyc","oxidative cleavage;of a glycoside",0,20,16,[[22,942]],[[23,1089],[0,0],[0,0]]]
)//eod