CHEM 2021 Chapter Notes - Chapter 2: Hydroxylamine, Hydrazone, Carboxylation

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7 Feb 2016
Department
Course
Professor
CHEM20213.0 2015
ListofReagentsCovered
acid(includingaqueousacidH3O+)
whendilute,asageneralsourceofH+inworkupsteps,quenchinganionsanddisplacingmetals(e.g.Mg,Al,etc.),
forinstancetoliberatethealcoholfromthealkoxideformedfromaGrignardadditiontoanaldehyde
usedinconcentratedform(usuallyH2SO4orH3PO4)foracidcatalyzeddehydrationoftwoequivalentsofa
alcoholtogiveasymmetricalether,witheliminationofH2O(bimoleculardehydration);thehygroscopicacid
simultaneouslyactsasadehydratingagent
inacidcatalyzedringopeningofepoxidesbyweaknucleophiles(H2O,alcohols,Cl,Br,etc.)atthemostsubstituted
end
inacidcatalyzedreactionsin
Fischeresterification(carboxylicacid+alcohol6ester+H2O)
hydrolysisofesterstogivecarboxylicacids&alcohols(reverseofFischeresterification)
formationofhydrates,hemiacetals&acetalsfromaldehydes&ketoneswithwateroralcohols
regenerationofaldehydes&ketonesfromhydrates,hemiacetals&acetalswithwater
formationofiminocompounds(imines,oximes,hydrazones)fromaldehydes&ketoneswithamino
compounds(NH3,amines,hydroxylamine,hydrazines)
regenerationofaldehydes&ketonesfromiminocompounds(imines,oximes,hydrazones)withwater
hydrolysisofamidesandcyanogroupstogivecarboxylicacidsandNH4
+
hydrationofcyanogroupstogiveprimaryamides
seealsoHNO3,H2SO4
acidchlorides
usedinmakingcarboxylicestersofalcohols
usedinmakinganhydrides
usedinmakingamidesfromamines
usedinmakingaromaticketonesfromnondeactivatedareneswithAlCl3
canbereducedtoaldehydeswithLiAl(OtBu)3H
notethatSOCl2andTsClarealsoacidchloridesformingestersoramidesasproductsorintermediates
Ag+
inoxidationofaldehydestogivecarboxylicacids(especiallyasAg2O)
intheTollenstestforaldehydes(silvermirrortest)
AlCl3
inchlorinationwithCl2ofarenestogivechloroarenes
inFriedelCraftsalkylationtogivealkylareneswithchloroalkanesasC+sources
inFriedelCraftsacylationtogiveacylarenes(phenones)withacidchloridesasacyliumionsources
alkoxideions
asnucleophiles,inthepreparationofethers(Williamson)withalkylatingagents(e.g.alkylhalidesortosylates)
asnucleophilesinringopeningofepoxidesatleastsubstitutedend
asnucleophilesinestersynthesisbyreactionwithacidchloridesoranhydrides
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