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Ortholpara directing Groups OH JEE Br Fe Ho l dy Torre Br ya FFS KI t Kp ortho Br ITE No raeta Para ke ortho 4 contributors w on oxygen t.i.EE it IT Ks wet oxygen EWG by induction H o th Higher sores IEEE Energy It Less Resonance pure 4 contributors w on oxygen H o is HA Br

JEE Ho t ya FFS ortho ITE Para ke t.i

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Ortholpara directingGroupsOH

JEE Br Fe Ho ldy Torre Br ya

FFS KI t Kportho Br

ITE No raeta Para

keortho 4contributors w on oxygen

t.i.EE it ITKs

wet oxygen EWG by inductionH oth Highersores IEEE EnergyIt LessResonance

pure 4 contributors w on oxygenH o

isHA Br

HozHoz Itt l No No orthoor

AzSOypara

Moz Meta

f to onlytwo

M402202

a 454t gtfopretty Noa

Fto EI's O 3 ae

a Hozit

of Noe Hoz

ILHANK

EDG ortho EWGIst f I Stp Stay2 St

T St meta

para

EDG are ortho EWG are metapara directors directors

CDG are activating EWG are deactivatingLower EA by Raise Ea bydirectlystabilizing destabilizingpositivepositivecharge charge

R

E i EE E's.no s

Hoz

Methyl Ethyl Isopropyl Tertbutyl

tg58.5

g45 30 1715890L 4.4 6.5g k 7.79 11.5

37.2 48.5 623 72.7

29.35 IX 29.35 41.47029.35 17 414 27 4,4 6.24.470 6.2

37.2 52.4 3721 52.4 Major70.95

it it g Eatsdy't e

EDGbyResEWG by Ind

g.BE ewabyInductonsgIJmore

strong IF EDG by ResonanceEw

FT EWG by Resonance

Es EFdy Febres dHE 1

Br

major

I l raB Tora ly

Ff Epht

HEABr minor

major

XP Bre I BrylyI 177 Febres 01 IFI 01 smaller

similar in Bvsize toethyl minorstronger EDGDirects major

9

gift o s OH

7 YEHHzS0y

footstool

at

Carbocation

Friedyl Craftsalkylakon

Ei7 TtyI rT to

EEelectrophile

B

AtChs

Taf ai I 0a At a a 41 Ce

Ce a

EEE i EE6 C 60 40

35 C 40 60

into Eat10 I

ohd FEE A

as I

OHd I

7Hzsoy 4

Carbocation strong electrophile

II IIe life 9 It nad

yRodes de

LE Ata e

g4 80 EYE't

O 010H HIa I

t.EE EE

E EE yBr 4 Bn

Ala Ymajor

Factscleats order of addition matters

Br Ats for substitutionpattern

Iss EFa

EiazClemmensonRan

ahipCl

Clemmensen Reduction

110 InHgACT A

Wolff Kishner Reduction Hq rig'tHO HzNNHz koH HydrazineW a