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    In organic chemistry, molecules generally do not react with each other due to electronic repulsion. For a reaction to occur, molecules must overcome this barrier by having orbital overlap or charge interactions that bring them close enough for electron transfer. Nucleophiles are molecules that donate electrons, such as those with lone pairs of electrons. Electrophiles are molecules that accept electrons, such as those with low-energy empty orbitals. For a reaction to be favorable, the interacting orbitals should be close in energy so that electrons can readily flow between the nucleophile and electrophile.

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    In organic chemistry, molecules generally do not react with each other due to electronic repulsion. For a reaction to occur, molecules must overcome this barrier by having orbital overlap or charge interactions that bring them close enough for electron transfer. Nucleophiles are molecules that donate electrons, such as those with lone pairs of electrons. Electrophiles are molecules that accept electrons, such as those with low-energy empty orbitals. For a reaction to be favorable, the interacting orbitals should be close in energy so that electrons can readily flow between the nucleophile and electrophile.

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    13 views5 pages

    WJL Oc C5 1 2

    Uploaded by

    yang ma
    In organic chemistry, molecules generally do not react with each other due to electronic repulsion. For a reaction to occur, molecules must overcome this barrier by having orbital overlap or charge interactions that bring them close enough for electron transfer. Nucleophiles are molecules that donate electrons, such as those with lone pairs of electrons. Electrophiles are molecules that accept electrons, such as those with low-energy empty orbitals. For a reaction to be favorable, the interacting orbitals should be close in energy so that electrons can readily flow between the nucleophile and electrophile.

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    of 5

    Organic chemistry Chapter5 organicreactions

    whymoleculesgenerallydon'treactwitheachother
    Aim whysometimesmolecules reactwitheachother
    do
    Howmolecularshapeandstructuredeterminereactivity
    Inchemicalreactionselectronsmovefromfueltoemptyorbitals
    andelectrophiles
    Identifyingnucleophiles
    Representingthemovement
    ofelectronsinreactionsbycurlyarrows
    chemicalreactions

    Notallcollisionsbetweenmoleculesleadtochemicalchange
    Reautionsoccuronly if apairofmoleculeshaveenoughenergytoovercomethesuperficialrepulsion
    Theminimumenergyrequiredforareaction activationenergy

    chargeattractionbringsmolecules
    together
    Amorecommoncauseoforganicreactionsisattractionbetween achargedreagentcacationoranionandan
    organiccompoundthatarebothdipole
    stableorganicanionsmoreusuallycarrytheir
    negativechargeonanatomthatisnot
    carbon onoxygenforexample asintheacetateion a13 coi

    Itisn'tnecessaryforeitherreagenttobecharged

    I
    Orbitaloverlapbringsmoleculestogether

    Tosummarizethesituation
    Ingeneralmoleculesrepeleachotherandneedtoovercomeabarrierwithaminimumamountofactivationenergytoreact
    Mostorganicreactionsinvolveinteractionsbetweenfullandemptyorbitals
    Manybutnotall alsoinvolvechargeinteractionswhich helpovercomeelectronicrepulsion
    someionicreactionsinvolvenothingbutchargeattraction

    Reactionshappenwhenelectronsflowbetweenmolecules
    Mechanism ofthereaction thedetaileddescriptionofthepathwaytheelectronstake
    themoleculeacceptselectrons
    Electrophile

    Nucleophile the
    moleculedonateselectrons

    on
    Ndonatesbothelectronsforformingbond dativecovalentbond
    fromoneatom
    Dativecovalentbondisjustanordinary6bondwhoseelectronshappentocome

    orbitaloverlapis essentialforsuccessfulreaction

    Nobondforming

    Thebestreactionsareonesinwhichtheenergiesoftheinteractingorbitalsaresimilarinenergy
    Fora reactiontotakeplacemoleculesmust
    overcometheir electronicrepulsionbychargeattractionand or orbitaloverlap

    haveorbitalsofappropriateenergytointeract afilledorbitalonthenucleophileandanemptyorbitalonthe
    electrophile
    approachearnothersuch thattheseorbitalscanoverlaptoforma bondinginteraction
    Organic chemistry Chapter5 organicreactions
    Nucleophiles andelectrophiles

    wecanignoreourinteractionsbetweenpairsof
    filledorbitals1bondingandantibonding cancelout
    andpairsofunfilled orbitals
    um
    nucleophiles

    andelectrophiles

    Thebestnucleophileshavehighenergyoccupiedmolecularorbitals Homos
    Thebestelectrophileshavelowenergyunoccupied molecularorbitalsCLUMOSI

    Identifying a nucleophile
    negatively charged
    Nucleophiles

    neutralspecieswithapairofe onHomo
    Yostcommoni havenonbondinglone
    pairofe
    witha lonepair

    paiszszpbzsz.ph s 1525450353p4

    theirlonepairsareevenhigherenergyoccupyingorbitals
    madeupof 3s and 3p atomicorbitals

    Anionswhichhavelonepairs areoftengoodnucleophilestoo 1nucleophileswithanegativecharge


    Thenegativechargecannotbeassigned
    tooneofthe lonepairs inparticular

    Negativecharges likethisactuallyrepresents apair electrons boththeextraelectronanditspartnerinthe


    of
    lonepair sowenormallywrite mechanismswithanarrowstarting onnegativecharge
    bonding a orbitals especially cdoublebonds
    The common 2nucleophilesarealkenesandaromaticrings
    only

    6bondassociatedwith electropositiveatoms suchas Bisi orthemetalsalongwithCorH

    The6orbitalgeneratedfromelectropositiveCandevenmoreelectropositive Li
    ishighinenergy

    Identifying an electrophile
    Electrophiles are neutralor positivelychargedspecieswithanemptyatomicorbital1suchasthe
    empty porbitalinborane or a lowenergy antibondingorbitalthatcaneasilyaccepte

    Electrophiles withan emptyatomicorbital

    InmostorganicelectrophilestheWMDsarelowenergyantibondingorbitalsassociatedwith
    electronegative atoms Cat or 6
    with a doublebondto an electronegativeatom

    1
    zitislower
    inenergythan
    the6 orbital
    withasinglebondtoan electronegativeatom in o

    Some6bondsareelectrophiliceventheyhavenodipoleatall eg 7v Brzand42

    Summary

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