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BENZOYL AMINO ACIDS 52020 Main points Ran itself PHeffects Mixed SolventRecrystallization NMR exchange Beadier CNV acyl subst p 919 920 Klein 0 O or G O ICI 11 yo 0 Ph na ph's so Phs NT benzoyl chloride of r YA n o Nasty Ala at highpty l H H O H in presence Reactive of NaOH H O add NaOH 0 add tea in gradually while phsnnroHL phrnn.ro 0 Monitoring pH H O H o insoluble in soluble in basic if o J T benzoic acid aqueous acid solution pH effects Zwiterion mum pngsioi.pnizqgoqIonA atbNTj oHI.H.info uannq o o Product ph go OH I ph µ o_O Mixed Solvent Recrystallization to I create satd solve cetotenere idea so can shifteguil back 1 forth To notsglfzbokhernegfBAS.net E BACK solubility Lifone solvent won't work work on its own Two approaches mixed solvent recryst use premixed solventmixture procedure not best practice Better way Csee video Cratchit dissolve compound in just envf of solvent in which Cfote bp 78 C its more soluble Chigh To C Eton good solvent H2O bploooo addjustenuf ofsolvent in whichcompound is less soluble c bad solvent until wstdoudy Cshil heating add justenufof 1st solvent just dissolves to

NMR CNV Klein ph's YAhomepage.smc.edu/kline_peggy/Organic/Lab_Reports... · BENZOYL AMINO ACIDS 52020 Mainpoints Ran itself PHeffects Mixed SolventRecrystallization NMR exchange Beadier

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Page 1: NMR CNV Klein ph's YAhomepage.smc.edu/kline_peggy/Organic/Lab_Reports... · BENZOYL AMINO ACIDS 52020 Mainpoints Ran itself PHeffects Mixed SolventRecrystallization NMR exchange Beadier

BENZOYL AMINO ACIDS 52020Mainpoints Ran itself

PHeffectsMixed SolventRecrystallizationNMR exchange

Beadier CNVacylsubst p 919 920 Klein0 O

or G O ICI 11 yo 0Ph na ph's so Phs NTbenzoylchloride of r YA n oNasty Ala athighpty l H H O H

inpresenceReactive ofNaOH H O

addNaOH 0 addtea ingraduallywhile phsnnroHL phrnn.ro 0

Monitoring pH H O H oinsoluble in solubleinbasicif o J T benzoicacid aqueousacid solution

pHeffects Zwiterionmum

pngsioi.pnizqgoqIonAatbNTjoHI.H.info uannq

o o

Productph go OH

I ph µ o_O

MixedSolvent Recrystallizationto I createsatd solvecetotenere

ideaso can shifteguilback1forthTo

notsglfzbokhernegfBAS.net E BACKsolubility Lifonesolventwon'twork work onits ownTwoapproaches mixed solventrecryst

use premixedsolventmixture procedure notbestpracticeBetterwayCseevideo

Cratchit dissolvecompound injustenvfofsolventinwhichCfotebp78C its moresolubleChighTo CEton goodsolventH2Obploooo addjustenuf ofsolvent inwhichcompound islesssolublec bad solvent untilwstdoudy Cshilheating

addjustenufof1stsolvent justdissolvesto

Page 2: NMR CNV Klein ph's YAhomepage.smc.edu/kline_peggy/Organic/Lab_Reports... · BENZOYL AMINO ACIDS 52020 Mainpoints Ran itself PHeffects Mixed SolventRecrystallization NMR exchange Beadier

JLsat'd solnUsual cool toRoom't cool nice bath

1fool toofast trap impuritiesVacuum fltratois use solventinwheohitslesssolubletotransferIwash If impdissolved

itNummRAnalysis as

Two spectra compound inDMSOde CwlResidualDmsodsttracesHeoabove Dao time

Go over Benzoylglycine spectra fr productsofallthreeAA are linkedonline2 no c F R

INITIALLY DsplitbyNH Hoo µ O H11 H

o H o

INN OH bromaerdgesdnfetettr.com RAHbondingH Normalrcoanverydownfield Rduetohydrogenbonding 397Techniquesbook

TCsplitby He µveorsdownfield exchange x fastexchangeAntiH NMRTimescale

isslow slowit

f4ToGfyveE onoexchangexx slowexchange

when add Dao waitPh if OH Dao Ph g oD

California Chrome - Los Al - Dec 2016

Page 3: NMR CNV Klein ph's YAhomepage.smc.edu/kline_peggy/Organic/Lab_Reports... · BENZOYL AMINO ACIDS 52020 Mainpoints Ran itself PHeffects Mixed SolventRecrystallization NMR exchange Beadier

NMR spectra Clinked from webpageand fwm Canvas

HuhwHhD

b

Page 4: NMR CNV Klein ph's YAhomepage.smc.edu/kline_peggy/Organic/Lab_Reports... · BENZOYL AMINO ACIDS 52020 Mainpoints Ran itself PHeffects Mixed SolventRecrystallization NMR exchange Beadier