Scribd Logo
Upload

Welcome to Scribd!

  • WJL Oc C6 1 2

    Uploaded by

    yang ma
    6 views2 pages
    This document summarizes key aspects of nucleophilic addition reactions to the carbonyl group. It discusses how molecular orbitals explain the reactivity of the carbonyl group and the general two-step mechanism of nucleophilic addition. Specifically, it focuses on the reaction of cyanide with aldehydes and ketones to form cyanohydrins, including favorable conditions, reversibility, and effects of substituent size. Steric hindrance from large substituents is also briefly mentioned.

    Original Description:

    Original Title

    WJL-OC-C6-1-2

    Copyright

    © © All Rights Reserved

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    Report this Document
    This document summarizes key aspects of nucleophilic addition reactions to the carbonyl group. It discusses how molecular orbitals explain the reactivity of the carbonyl group and the general two-step mechanism of nucleophilic addition. Specifically, it focuses on the reaction of cyanide with aldehydes and ketones to form cyanohydrins, including favorable conditions, reversibility, and effects of substituent size. Steric hindrance from large substituents is also briefly mentioned.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    6 views2 pages

    WJL Oc C6 1 2

    Uploaded by

    yang ma
    This document summarizes key aspects of nucleophilic addition reactions to the carbonyl group. It discusses how molecular orbitals explain the reactivity of the carbonyl group and the general two-step mechanism of nucleophilic addition. Specifically, it focuses on the reaction of cyanide with aldehydes and ketones to form cyanohydrins, including favorable conditions, reversibility, and effects of substituent size. Steric hindrance from large substituents is also briefly mentioned.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    of 2

    Organicchemistry Chapter6 addition tothecarbonylgroup

    Nucleophilic

    Howandwhythe o groupreactswith
    nucleophiles
    molecularorbitalsandcurlyarrows
    Atm Explainingthereactivity ofthe ogroupusing
    whatsorts molecules canbemadebyreactions of G ogroup
    of
    Howacid orbasecatalystsimprovetheactivityofthe ogroup

    Molecularorbitalsexplainthereactivity ofthecarbonylgroup
    Narnthis
    04 TO alcohol
    Huo W 78 yield

    No 017 9 to noTO T H protonation


    addition
    nucleophilic additionsto carbonylgroups
    ofan tothe t isthegeneralfeatureofannucleophilic
    carbonylgroup

    Additionstocarbonylgroupgeneraly consist
    oftwomechanisticsteps
    nucleophilic attack onthecarbonyl
    group
    Protonation
    of theanionthatresults

    planar Thepolarizationin a
    bondmeans it is
    skew towardsoxygen
    becauseoxygen ismore
    electronegativethanC

    converselythe unfilled
    atantibondingorbital
    isskewedintheopposite
    direction

    whyc o is soreactive IEvenshorterandwithhigherenergythec o

    polarization
    Thepolarizedo_0bondgivesthecarbonatomsomedegreeofpositivechargeandthisattractsthenegativecharge
    ofnucleophiles likecyanide
    Thepolarizationof at antibondingorbitaltowardsC LUMO
    CN HOMO is an SPorbital oncarbon
    Organicchemistry Chapter6 Nucleophilic addition tothecarbonylgroup

    Attackofcyanideonaldehydesandketones

    Nam Nc on
    KTH HaoHu k H
    orbitalsofthecyanide ion aldehyde product cyanohydrin

    I
    N C0 f
    0
    ENT119 N THto
    KAH R H

    cyanohydrinsin synthesis

    cyanohydrinformation isreversiblejustdissolvinga cyanohydrininwatercangivebackthealdehyde orketoneyou


    startedwith anaqueousbaseusuallydecomposed cyanohydrins completely
    cyanide is agoodleavinggroup

    Ho on
    rA r poke on
    ketone
    cyanohydrin
    a
    no9 o un
    t e l
    od
    n un
    ri on
    f r r r
    cyanohydrinformation favorablefor
    is anequilibriumbetweenstartingmaterialsandproducts theequilibrium ismore
    attachedtothecarbonyl atom
    carbon
    aldehydecyanohydrinthan forketonecyanohydrinsduetothesizeofthegroups

    sterichindrance
    from
    thatresult
    Effects thesize ofsubstituentsandtherepulsionbetweenthemarecalledstericeffectsandwecallthe
    bylargesubstituentssterichindrance
    forceexperienced
    repulsive

    Itaffectsreactionratesbutalsomakemoleculesreactbycompletelydifferentmechanisms

    You might also like