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General Organic Chemistry For Iit - Aipmt - Aieee
General Organic Chemistry For Iit - Aipmt - Aieee
General Organic Chemistry For Iit - Aipmt - Aieee
GENERALORGANICCHEMISTRYFORIIT/AIPMT/AIEEE
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4.Classificationofreagents
(a)Electrophilicreagents(Electrophilies):
Asthenameimplieselectrophilic(electroelectron,
philelove)reagentsareelectrongseekingorlovingandthusattackthesubstancesatthepointof
maximumelectrondensity.Thusanelectrophilicreagentoranelectrophileisaspecieshavingelectron
deficientatomorcentre.Theelectrophilicreagentmaybepositivelychargedspecies,orneutralmolecule
withelectrondeficientcentrre.Someoftheimportantelectrophilesaregivenbelow.
Itisinterestingtonotethatsinceelectrophilesarecapabaleofacceptingelectronspair,theyareLewis
acids.
Thereactionsinvolvingtheattackofelectrophiliesareknownaselectrophilicreactions,vizelectrophilic
additionandsubstitutionreactions.
(b)Nucleophilicreagents(Nucleophiles):
Thereagentspossessingatleastonelonepairofelectronsare
knownasnucleophilicreagentsornucleophiles(nucleonucleus,philelove).Sincetheypossesshigher
electrondensity,theyattackthesubstrateatthepointofminimumelectrondensity.Thenucleophilic
reagentmaybenegativelychargedspeciesorneutralmoleculewithfreeelectronpair(s).Someofthe
importantnucleophilesaregivenbelow.
Thestarindicatestheatomthatdenoateselectronstothesubstrate
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5.TypesofOrganicReactions
(a)substitution(displacment)reactions:
Thedisplacmentofanatomorgroupfromamoleculebya
differentatomorgroupisknownassubstitutionreaction,e.g.
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Substitutionreactionsarefurtherclassifiedintotwotypesdependinguponthemechanism:
(i)freeradicalsubstitutionreactions:
thoseinwhichfreeradicalsareformedasintermediatesand
(ii)ionicsubstitutionreactions:
thoseinwhichionsareformedasintermediates.
(b)Additionreactions: Reactionsinwhichatomsorgroupofatomsareaddedtoamolecule(i.e.thereis
simplyanetgainofthereagentatomsintheproductmolecule)areknownasadditionreactions.Thistype
ofreactionoccursonlywhenthereisacentreofunsaturationinthemoleculewhichisgenerallydueto
thepresenceofamultiplebondbetweenatoms,e.g.
Likesubstitutionreactions,additionreactionsmaybeinitiatedbyelectrophilies,nucleophilesorfree
radicals.Henceadditionreactionsmayalsobeofthreetypesdependinguponthemechansim
electrophilicadditionreactions,nucleophilicadditionreactionsandfreeradicaladditionreactions.
(c)Eliminationreactions:
Asmentionedearlier,eliminationreactionsarereverseofadditionreactions
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andinvolvetheloseofatom(s)orgroup(s)fromamoleculetoformamultiplelinkage.Mostcommonly,
lossofatomsorgroupoccursfromadjacentcarbonatomstoyieldanolefin,e.g.
(d)Rearrangements:
Rearrangmentreactionsinvolveeitherthemigrationofafunctionalgroupto
anotherpositioninthemoleculecontainingadoublebondorthereshufflingofthesequenceofatoms
formingthebasiccarbonskeletonofthemoleculetoformaproductwithnewstructure.Forexample,
6.FreeRadicalMechanism
Thereactionbetweenmethaneandchlorieninthepresenceoflightisatypicalexampleofthesubstitution
reactioninvolvingfreeradical.Themechanismofthisreactioninvolvesthefollwoignthreesteps.
1. Initiation(Formationoffreeradicals)
2. Propagationoffreeradicals
3. Terminatinstep(Terminationoffreeradicals)
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7.ElectrophilicSubstitutionReactions
ThesearegenerallywrittenasSE(SforsubstitutionandEforelectrophilic)andaremorecommonin
aromaticcompounds.Nitration,halogenationandsulphonationofbenzenearefewexamplesofthistype
ofreactions.Themechanisminvolvesthefollowingthreesteps.
1. Formationoftherealelectrophile
,e.g.nitroniumioninnitration.
2. Attackofelectrophileonbenzene
3. Eliminationoftheprotontogivesubstitutionproduct
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8.Nucleophilicsubstitutionreactions
Nucleophilicsubstitutionreactionsarethosesubstitutionreactionswhichinvolvetheattackofa
nucleophile.TheseareusuallywrittenasSN(SstandsforsubstitutionandNfornucleophilic)andare
morecommoninaliphaticcompounds.HydrolysisofalkylhalidesbyaqueousKOHisanexampleof
nucleophilicsubstitution.
Thenucleophilicsubstitutionreactionsmayfollowtwomechanism,viaunimolecualrandbimolecular.
(a)Unimolecularmechanism:
Nucleophilicsubstitutionreactionsproceedingviaunimolecular
mechanismareusuallyabbreviatedasS
N 1reactions(Sstandsforsubstitution,Nfornucleophilicand1for
unimolecular)
Therateofsuchreactionsdependsonlyontheconcentrationofthealkylhalide(substrate)and
independentofbase(nucleophile).
Suchreactions(S N1reactions)arebelievedtobecompletedintwostagse.Inthefirststagewhcihisalso
theratedeterminingstep(slowstep),thealkylhalideionisestogivecarboniumion.Inthesecondfast
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theratedeterminingstep(slowstep),thealkylhalideionisestogivecarboniumion.Inthesecondfast
step,thecarboniumioncombineswiththenucleophilicreagenttoformthefinalsubstitutedproduct.
(b)Bimolecularmechanism:
Nucleophilicsubstitutionreactionsproceedingviabimolecularmechanism
areusuallyabbreviatedasS N2reactions(2standsforbimolecular).Therateofsuchreactionsdependson
theconcentrationofthealkylhalide(substrate)aswellasthebase(nucleophile).
Suchreactionsarebelievedtobecompletedinonestep
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