Addlcinformofcarb.aeBrNga cN OH

mustbe o c NfHzOmy NRor stereos OfBr no Il OA 30 carb

Br MgBr Whooi Mg

fBr a.co ycozH3 HzOt

Br coast

E i0 excess O

HAC XXH a H Naut h H

E II

we

more BREWGacidic

3NH3

IEE i noo n oacid 1 GlfPBrs Br 4h20 Br

O OHBr µ B Broacidic Br BrHo PBR

IIABr

8Br touts5

Keto o

He BEnd OH

ICy EC Gal

o 05io HFKBr O7rpBr sHffoHneutralBrBr Br G

µ c Acyl Suba B Br

O of't LIl 11

FOH OHBr Br

Gabriel Ti OOH

Sym a LgAHry.BR The

o HOTN source

afoot8 HIMbasic

Br 1 NANI2 LAH 3H2O

HsN coE neutral

s

Wohl Degradation CN

NBL JEN Ac EEN 5H C He B f

WINNIE LGGabriel Synth NV

Azide HIpen Nz t RNHZ

Imine HydrolysisIt t It t Hy

IRI to Pi t Ha R2

Nitrile HydrolysisR CIN Rhoa t NHy

Amide hydrolysisRIENHz 5 RIO t Hy

Wolff Kishner

a.eu EtEo EEmtIEhEketone

amideRacemic red nmix mechFormed when group can

attack top or bottom face of

no PBI Br yztyay.BR

Bry Brtattacks top IboHom

Br fof Br implies Br BrIl HOH OHOH

go 50 mixture ofenantiomers

i i i em

I

IHOT to 0 1

iHt babHclepimers

Hof of NOT enantiomers

Ho f NOT racemic

RED AMIN 0 H

cont ft if gHN

Ho orTojo

bottom HN Har

HEH HN H ofZE.peLego restneutral basic

in IE7 tirHt f

HO l

E i H Tito

G breaks f H

WH 2291 YA o A H

TNR TNR Li yGpkar

NH 12

Arg Antz ska tHN l go Cys

o

H.N fgit.TK Yoopka2

pKazArg 1o_09

TyrpkarlopH 2 7cpHL9 Oncharge

2cpHL7 9 pH 40 I102pA 42 2

few pH 12 3

ID aldose tetr

2 Ho CHI D ketoseHoHt

x o_0

Haight12400 o

Hot.to H5triacylglycerol16y

NIH

phospholipids