H2 chem organic reactions

Alkanescombustion: (xHy+(x+1)02->XCO2+=H20 provideenergytoinitiatethehomoyt aradicalsFreeRadicalSubstitution n+1Ct2(g)/Brz(g),UVlig->briefexposureasUVlightproducesX-radicalsthat initiatechainreactionsofpropagationsteptoproduce moreradicalsforrxntosustain CH4+Cer- >CHice+HCe ⊥ChaltpredominatesmyexcessCH4 mechanism CCt4predominateswyexcess(tr Initiation Ratioofisomericpots Ce - ratioofpatscalculatedfromnumber ofHatomsofsamechemicalenvironment thatcanbesubstitutedtoformaparticularisomer Propagation - differentputsduechemicalenvironments ofIfatoms wis+--> CHz+H= C cris-c-43 H· crz+Cf- Cl 4)n- >CH3+C· sub· Hiatomsgive-entropropanewhilesubHbatoms se give2-chloropropane itto- Cuc+H 3fordisubstitutedpat · cricce+Cf-1- >CHIC+C· 444 de termination(atleast3) Aptey- >Crz-c citey. ->C- 1 yCH3->CH3-CHy

Alkenes Reduction - H2(g),Nicatalyst,heat - Hzlg),Pd/pEcatalyst,roomtemp.BrBr ElectrophilicAdditionH--BrOr- BrzincCly,roomtemp & -HtHBr-- Br,199),roomtemp - HX(9),roomtemp->H-industrial- H20(g),300%,Goatm,conc. Hypoycatalyst &H-H - conc. H2SOy,H20,heat in laboratory carbocationonCwmore/leastwithdrawinnote mechanism ↓ * Br+Br Br +ButAtI purplekMno4 purplekMnOydecol, Oxidation↑decol ↑brownppt. ofMnOz mildoxidation:KMnOy,HeSoy(aq, Cold/KMnOy,NaOHal C=+H+[]->H-C- 2-H purplekMno4 purplekMnOydecol, ↓Wi ↑decol ↑brownppt.ofMno- strongoxidation/oxidativecleavage:KMnOy,Hesoycad,heatunderreflux/KMnOy,Naorcad,heatunderreflux oro11 F= - >Con+H20 HO-c- Cop+[0]->2COn+H20⊥cost- inalkalineconditions R-C= ->R-==0 carbadR0inalkalineconditionsH- HO- - ↑C= - >=0Ketone

Arenes &HofhydrogenationofKE=-354k5mol &HofhydrogenationofL=- 208kJmol+ diffinactual&expectedvalueofCH=146kJmol ⊥resonanceenergy->measureofstabilityofbenzeneduetodelocalisationofitselectrons- Benzene topreventFexs/AlXsfrom ElectrophilicSubstitutionundergoinghydrolysisw,water reactswithX2to siformFeX3 - Brz(1)/Ct2(g),anhydrousFeXy/AlXs/finelydividedFecatalyst,roomtemp.. FeltsactsasLewis - RCt,anhydrousFects/Afctscatalyst,roomtemp. 3acidcatalystbyacceptinganelectronpairfromC2- conc. HNO,(aa),conc. H2SOy(aq)catalyst,heatunderrefluxat55° Cz HesoyactsasaBronsted- Lowryacid bydonatingaprotontoHNOz Mechanism(Lewisacidcatalyst) Alces+Chr=Afcep-+cetor FeCts+CHiCHcCEFeCtp-+CHsICH2 HCH2CH3 #HXCH CH2CHy 1FecetI #[Y+He+Fects Mechanism(Bronsted- Lowryacidcatalyst) HNOs+H2SO4=NOct+H20+HSoy- ToA tivoSlow --> NOr H H methylbenzene,ElectrophilicSubstitution - conc. HNOs,conc. H2SO4,30° C- >lowertemp:electrondonatingalky/group↑reactivity Ssubstitutedat - Brz(1)/Ct2(g),anhydrousFeXy/AlXs/finelydividedFecatalyst,roomtemp. 2,4positions - Ce2(g)/Brz(g),nrlight(FRsofCH3sidecharn)

Oxidation- kMnO+caqi·H2SO4(aq),heatunderreflux->purpleKMnO4decol. - kMnOx(aq))NaOH(aq),heatunderreflux->purpleKMnO4decol. >brownpptofMnO CH2CH2CH3 coort fromexcess[ - +9703- >[+2C2+3420 CrIzCH3 coo- +Oto]+30H->F+Gs"+4t FurtherrxnsforR-CN: Alky)HalidesRX+NaOH-Ron+NayHydrolysis- H((9q)/H2SO4(aq),heatunderrefluxR- CN+HCl+2H20->R-C004+NHyce NucleophilicSubstitution↑ -NaOH(99),heatunderreflux R- CN+NaOH+H20->R-200-Ngt+NH3 Reduction- NaoH(aq),heatunderreflux-- LiAtHyindryether,roomtemp. R- CN+4[H]-R-CHINH2->Amine - ethanolicNaCN,heatunderreflux - Nainethanol - excessethanolicNH3,heatinSealedtube- Hu(g)w/Ni/pd/ptcatalyst↓ heat roomtemp↓ 110amine) CHyCHeX+INH3- >CH3CHzNH2+NH4X CrcX+acobarizat-[CC)2N4+CHICHNNsY Sminetave : cryCHX+2 (CHICH2)2NH-(CHycgN+<Cric)2NHeX excessRY CHyCHzX+/CHzCH2)sN->(CH3CH2)yN++X- (30amine)(quaternaryammoniumsalt) EnergyMechanism M SN1(mostlytertiaryRX --- CH3-C5e5-> CH3-cit+- tCH3 Slow RXOrHO X-------- CH3 > CH3 CH3 RXnpathway CH3-OHAutCH3-C-OHRacemicmixture or CH3 CH3 ↑ rate= k[RX] Hac-cityOh #inSN2(mostlyprimaryRX) orCH3g-vi: - > Tic-r]- Nc -+Br Energy↑ minRCN+X- rate=k[Nn][RX] 4)HO ---- >Rxpathway

Elimination- ethanolicNor,heatunderreflux CH3-+NaOH CH3Ch↑NaBr+H20 H- H major HCH3 -c=c-H CrzCHzC=C-H H- CH3 minor orsaytneff'srule: majorpdtiswitSeed DistinguishingTests FindXinRX 2nucleophilisub o,Method1: - AddNaoH(aq),heat - AddHNOs(aq)->removeexcessOH-/preventAg20ppt) - AddAgNOz(aq)+formAgXppt RI->immediateyellowppt R-Br- >immediatecreamppt R-cl- >immediatewhiteppt (8)- X- >noppt O Il Method2:- AddethanolicAgNOs/ethanolicsilverethanoateCHy-o-Agt- warmmixtureinwaterbathat50% ->formscarboxylicacid RI->immediateyellowppt R-Br->creampptformedafterawhile Irateofhydrolysisdependon strengthofC-XbondRcl-whitepptafteralongtime (8)- X- >noppt O IlFind19/2%%3° RX - AddethanolicAgNOz/ethanolicsilverethanoateCH3-o-Agt- warmmixtureinwaterbathat50% 1RX->pptformedafteralongtime - ethanolformhydrogenbondsw,H20,hinderingrxn 3RX->pptformedimmediately & - rateofSv2dependonLNu],:ethanolslowsdownSN2 20RX->pptformedafterawhile,thickensw,time-rateofSilindependentof[Nu]

HydroxyCompounds Alcohols Reduction ->veryweakacid - sodiummetalatroomtemp- - doesnotreactw/NGOH ROH+Na- >RO-Nat+EHr⊥strongnucleophile iCondensation ->RC-OH+ROHERO-R- carboxylicacid,conc. H2SO4,heatunderreflux - acylchloride,roomtemp- -R2-ce+ROH->R-0-R+42⊥e. g.methylpropanoate↓alcoholcarbacid/acy)chloride Oxidation i ->10alcohols- >R- C- OH - K2Cr20+(aq)/kMnOplaq),Hesoy(aq),heatunderreflux2alcohols- >R-C-RketoneY- K2Cr20y199),H2SO4(aq),heatwithimmediatedistillation3)alcohols- >norxn ↓ orangeKz[r0> *controlledoxidation turnsgreen Palcohols->R--HaldehydeP Elimination- ExcessCouc. H2SO4,170° Sfollowsayzeft'srule- Heatw,AtzOs,350% NucleophilicSubstitution(halogenation)preferred:canseparatenAs - PC5,roomtemp(RX+ Poc3- soCtz,roomtemp(RX+HCe+So2) Cl - dryHC,anhydrousInCezCatalyst,heatunderreflux &*willundergonucleophilicsubmyalcohol- PBrs(Brzw/redphosphorus),roomtemp. ZBrBUTNOTcarboxylicavid- NaBr,conc. Hysoy,heatunderreflux - I2wyredphosphorus,heatunderreflux- Nal,conc. HBPO4,heatunderreflux37 IodoformTestLoxidation -NaOH(aq),In199),warm Cry R-C- OH+4IntGNaOH- >CHIstR--oNat+5 Nal+5H2O i 4655 methylalcohol neededforrxn (CHzcanbeCHcl,CHIzetc]

Phenol Reduction - Sodiummetalatroomtemp- #- OH+Na- >70- Nat+IH2 Acid-Base- NaOH(aq),roomtemp. &OH+NaOH- >FO)- oNat+H20 Condensationvic I- phenolw,pyridineassolvent- >foraliphaticacylchloride+>: aliphaticundergo ndrolysis - phenolw/NaOHassolvent->foraromaticacylchloride ElectrophilicSubstitution 4- diluteHNOz,roomtemp. Ymonosubstituted - BrzinCCly,roomtemp. = conc. HNOs,roomtemp. Imultisubstituted(2,4,6-trinitro/bromopheno - Brz(aq),roomtemp ComplexFormation - neutralFelts(aq),roomtemp. ⊥purplecolourationobserved CarbonylCompounds NucleophilicAddition - HCNw,traceamountsofNaoH/NaCN,10 - 20% R INiR- C- R3+HCN->- - iketones I Mechanism NaOH+HCN- >NattCN+H2O NaCN->NOR+iCN R-S#H-CN R H - laston

cyanohydrinR-R Or Reduction R- C- R- LiAlHyindryether - CH2NHz- Nainethanol- H2w,pd/pt,roomtemp. /H2w,Ni,neat Or Hydrolysis ->R- C- R+H++20->-+N- DiluteHf(aq)/H2SO+(ag),heatunderreflux IN- NaOrcaq)/koH19q),heatunderreflux ⊥Or I R- C- R+OH+H20->RNH IN Oxidation- KzCro(aq)/kMnOy(aq),HeSoplag),heatunderreflux ⊥aldehydes->carboxylicacid Ri-H+[0]+R--OH aldehyde 10alcohol ItReduction R- CP+2 CH]->R- C- OH- LiAtHyindryether,roomtemp. & it- NaBHy(aq)/NaBHyinmethanol,roomtemp. R- Hzw,NiCatalyst,heat/H2w/pd/Ptcatalyst,roomtemp. R-C+2[H]+R- C- OH it condensation(rxnw/2,4-PNPH)- 2,4- DNPH,roomtemp ketone 2° alcohol H↑ 20NoR R Nozaldehyde/ ↓ketone 2,4dinitrophenylhydrazine orangeppt. AldehydevsKetoneTests(oxidation) 2513 - Fehling'ssolution,warm- >brickredCuroppt,bluesol decol. RCHO+2cut+50H- >RCO2+Cu20+3H20 ⊥onlyaliphaticaldehydes - Tollens'reagent,warm- >silvermirror RCHO+2Ag++30H- >RCO2+2Ag+2H20 ⊥AllaldehydesCaliphatic/aromatic)the 2322 LodoformTestCoxidation) - NaoH(aq),12(aq),warm O R-- Crz+3 I2+HNaOH->CHIz+R-C-oNat+3Nal+3420 3433

CarboxylicAcids&Derivatives CarboxylicAcids Reduction- Na(oranyreactivemetalCH3CO2H+Na->CHzCOn-Nat+EH Neutralisation- NaOH/KOH CHyCO2H+NaOH- >CH3CO2 Nat+H2O - NaCOz(s)/(aq)/NattCOs 2CHyCO2H+NazCOs->2CHzCOzNat+CO2+H2O Condensation - Alcohol,conc. Hesoy,heatunderreflux i P HaC-OOHH-OCHICH3=H3C-"OCHICHs+HeO Nucleophilicsubstitution(formAcylChloride) - PCl3,roomtemp. P