Organic chemistry Chapter5 organicreactions

curlyarrows representreactionmechanisms
curlyarrowsshowthemovementofelectrons
Acurlyarrowrepresentsthemovementof apairofelectronsfromafilledorbitalintoanemptyorbital

weakbond
whenthenucleophileattacksanantibondingorbitalsuchas Br Brbondwehavejustbeendiscussing weneed
twoarrowsonetomakethenewbondandonetobreaktheold

AttackofabaseonthestrongacidHBr

of
Noticethatthefinalarrowendsupdeliveringtheelectronstoanelectronegativeatomsatisfyingitsdesire
electrondensityThisispart thereasonwhydoubleor singlebondstoelectronegativeatomsareoften a
of
featureofgoodelectrophiles

Curlyarrowsalwaysstartonsomethingrepresenting a pairof es
A negativecharge
Alonepair
Abond
andendatthepointthose es aremovingto

chargeisconserved in eachstepof a reaction

Ifthestartingmaterialsarechargedthentheproductsmusthaveoverallthesamecharge

1430
1 iselectrophilic at Handnot0
whena abondisbrokenratherthan6bond onlythe abond wasbrokenandthe6 bondshouldbe

leftinplace
Xbond as nucleophiles

or

withatom specific curlyarrow

Twoionsreactwitheachother

withempty porbital

6bondas nucleophiles

or
w
He
LUM0thea orbitaloftheCeodoublebond
an'tstartfrom0 as itdoesn'tpresenta lonepairall8 e aroundtheBatomareshownas 4 B H
bonds

Theantonwhichformsis an intermediate notthefinalproduct

LUMoi O H o
Organic chemistry Chapter5 organicreactions
Drawingyourownmechanismswithcurlyarrows

whenyoumeetmins 1 identitywhichbondshavebeen formedandbroken

2decidewhichmolecule isthenucleophileandwhichistheelectrophile
eg
drawout
allbondsinvolved

nucleophile lonepair p
electrophile bondbetween candelectronegativeelement2
v

watchoutforfivevalentcarbons
Mostatomsinstableorganicmolecules have afullcomplementofneutrons twointhecaseofH eight
inthecasesofC Nando
so ifyoumake anewbondyoumustalsobreakanexistingbond

B c N oneverhave morethan 4 bonds Ifyoumakea newbondtounchargedH C Nor0you

mustalsobreakoneoftheexistingbondsinthesamestep
Mechanisms withseveralsteps

I
notreallytheproduct

t
e.g primaryalcohols canbeconvertedintosymmetrical others inacidsolution

theavidmustdosth
t hastobeelectrophile
f
t
b

eg

stepbystepguidetodrawmechanismswithcurlyarrows
Drawoutthereagentsasclearstructuresfollowingtheguidelinesin or
Inspectthestartingmaterialsandproducts andassesswhathashappened inthereaction
mostnucleophilic then
moleculesanddecidewhichisthe
Identifythenucleophiliccentres inallthereactant
identifyelectrophiliccentres
Drawcurlyarrowfromthenucleophiletotheelectrophile
considerwhetheranyatomthathasbeenchangednowhas
toomanybonds
writeoutthestructureoftheproductsspecifiedbythecurlyarrows
Repeat4 6 asrequiredtoproduceastableproduct