Cevie«;

a dchUJ(?.- ketone

o
uvkup) 0 0,
alcohols
03 IteØne
C C02 - product')
(Mechanism - oncettel 113 d(poloxh cuclooddlf/on )

DMS
o
CHs DMSO

(molomnide , tyi0)0bre) (ozonide)

bcgclic ompunds have atoms That axe aéQCenf.-
bridgu

PG&E _

lest
stDBe)
multiple lh the same molcales Llatd
bond Ion th isolata
alkme(Tb)< albne (T) üjugatea

_goujdion
lgmets- gone ad t« of aühC
giueoicomets - same conneoüVUbut different 3D sh
cis @me) #ans (diff) nea H
Z (gme) Z e (oppos) N/A
0 g-cig ( U/ ) & s-tvans (H/ )
[mue Ste-he, lec stableJ [les stab, morestable

gtobllltg

to moye tåz gteic, tb 9taRe

oleic aciÆ cig , Z , mce 9Wie , lag s-toue

GEE-JUMP
elmdicocu trans, E 18 staic, mue stable
 (dleoe-) SA, 1 addtticn pdoce

dlct(; additti) , an e additti), t;amo

first more gfab/e

042 allQ)e )

tkffìD-anfrol
Q) aleohol

ŒX) p-TgOH TP" , H20

order: moresubgtitiN oleohdg mrc —lg

* z.ûftgev
(9tQS) ptoùnat?—O Brn betu LQ LC fonn CO fonn CFC
,
b) 01131 albne—

alcohol POC13, . pgr&e OllQ)e

+) rayargemenf

O CQe-

O oyg-Cn van ent

@ anionja ou-cope

O Chjsea allglVlhdl ethas

Otbcbanjgno

concetecl 6e,- , klhCtjc gtaL(e

coocgatea, S-Cig
CPG Ihcyenseg
tô
Dienophfle at one TL bond
AJ02 E—C02CH3
]
Product en oraeg
e Oig / djenophifeIh, as / tong pyc&et_,
endo closer more les gtcbl@) exo (closer to C—C, lag stenc
TratrsifiQìState
• z and7 tic diale kJheticP , fond çrgt, , more stable louveytemp.

P , formel hlg)ff6 , les stable , îanp

moyegtoble p

(EX) Cp amer (dnrvœation )

endo
dlene diè)ophile amer )
vetYodie.EaUer rxn
,.f0 (endo, khetic, font)fagter Iowey )
di o
1-12.
10 (exo thomo, not fond , movesüL
o o hlghera-, gteic )
@ bgger cub daghes . dey 'ye Lunan* closer to
upt,uara fu rt}v frpm

GEE-JUY.{P
 No.

*VciQl
HO

CH
(enol)
allylie pknol

pyepl
H20 . I /L O

—OH

ff,CPBA e en 0 anti
p) CDS dto Ogoq OSO* C04
THF, Ä,
sty ( -OH) polar aprotic coluct [DMSO,ceďD nit?íle,

weak /Vu (1-120) po!or pctie

L2edJ30rs oxidaúcns
I

R x
Tollen€ Otbo.ylic acid ester acid haltde DBAL
o

PCC ald4L Ä)aBH4

OH OH

20 01001101

tg

• LAH Liůĺłpn ///ŕlde , LiAlH4

HJdľide, DIBAL- H
DIBAL Vieobugl ,41urnlhůrn

• /JabH4 godturn

• Jones 0 204, c
Hao, HOA
FiĽeľ Cr03 HOAc H20

PCC pgridĺbe, COB. HOI

NH40H
- (02), 1-120
1-1202
 NO.

retention

OCH3 R-OCH3

C! 13
09
Å(sCl cbl',tiæ)
o. , 40
Cl-h

OCH3
(cig) f)
ptå%idine,
( , ) ( TEA, )
ether enthesis ]
OJcohol + base alkoxide
us alkcxide halide ether ptoduct,
foster rxn
ketm
L pro J o

aceüc 40maldekyde benzotumone acetophæne benzoldeuu acetalde)ude

aliphatic Ejn
avomatie(41) coup
phO*Ql
L Prepoyatien J
Tennirnl alkgne