ir

Goc
!
o anicPeqe-h'on

fleq L+tn t WwLl

L ag
bond"t ar< bo4eo)
tnew botrl,r ar<- lrrVd )
Qeo.ne*
.gubstrel t ( ecLticJ,.

, ;;;;i^o, u! hr'ch teaXent ' SOeu'sa

t
afr'ac?s an .

is af*acxtrtl1 SubsLra*e )

5 +6+
:1 kry-
+ c*sot*kol
CH: -cl
tf nucleoPh ile
6uU,sftcle
R.rl ett-l €lertm ile .
( nucleua fuve'r)
(lrV t elraYS e louer)
(e- rich sP ,rr"b) r p
H ovi, of ,c[,8,
tl 1B(1
+
H c z cll tlnqe
LYe
cui , Nnz, Cltg-c?hb, ,Ctlz
R*,
israrq"d ,. 'r\ t'r i
ek'L{toPn'rc cl-f H,,
ilR-NHu &'N
le*{s H>o , Nlls, RailtgjQ'
$$,fitclg ,SAS,zndztBet)zt bnt:
e qe0,
i#,ih^n, { FeclgrSnclz $ncl'l 6 o tR'L[
MBoi', q'"'fi '
€rvr, b uerrt,
&,,n-i-*' ,t-r,'-ir-o+|-*
,s' { '[t
e-D
o
a
-t 8 ,
o
&1r-0" ' R-#i*
H2- R2 zo,
t
AltttLi
a

lte,
Prir rad,rtcal fg oko fs a electwfr'
+ e
I ale elcclvolnil
e H3o+ NH q ^oV
,,TBI#, b rdclea L

He\rol ht
Horno h'c
Bortdpab e sh;f+t +rwa^il
**w re n bo Fh
enuoll
anob.s fnorQ olecFao neSoJt've ahm I
s
cah'onfanlonUfnrtn
ft;- g -+ fi' +8"
A..*8 -) n+ +B-
(- ondttio gMil- ( giveo g norefo ) 1'g

'ltrt wb
' Low knP
' pYe*tnUt a
hhfotrUv,ry
ggy6xid.n u ' pxr-ltelLr- ob Palarsub's*ra"*e
a t't /, { . t ,t Palqr Salven*"
o tt /t ,rtonPrlav Jolveni
. t( // , ) i,irbe.tr.t+t
 Reaction lnkrrnedJnte
, Carbon free radical
" Cqrbocaliorr
, Qarbon'ion
, CarbenC' j
"nltyen e IX
, $enzlne I
Carbnt'on
Catbacah'ot\
Carbonfrec'rod'c'l

V< C
--? lbtt.volY h' c
lr/ I
H

HomolYlic devale
L-f

lnwmPl< oclof HeltiolXh'c

lnamPkte oc}et Lonplek otlr.*'
6e*
+e: 6e
+rnftHt+-I e S{able
,u!',Or#Hr fI ?.S*able -Y4,**t -' sl*blt
SP, sP b
S?,
Planar nan Pt$;;.tdat)
pLanav
learsarr',t I ell'rctrpUill- ou//l.ofhtlt
dcclaplu l't '
Dhnl* ,hll
Pararntjruhe
Req vtanqe*utf Psirlt " Ato (
No &auran1u1Y11wt J.'
Carbanion canbe
2- b v'd,tYedalso
\
cf12--cll'- 2
-o Pbna {
A t-\
tV,
o
@
tHz* lt*n
a mzn
\\ ect
0ttl/iucttve 4tu-f
o Ruonan* of filet CIrnerle
W*
**,,- furrnmn""t eW+
@ typerctnlya-tion 'fempra'1 LHuk
@ elutramev\c 4krt
ndu di v L
Llectronej q*;ve)ahtl? t's T elfac*
wlore
' Shlf Ha? ,b- a elutmn lowardc
n otNb on4 "
( it ontY woYxs F r r bond f.elfect o fun
a effe,y*ive uhfo 3 eavbon Cdistunn
d*ftHen+) a

+r <-ffe*
+f 2g+"4
e1,
9 C-N c
;6 ENX < ENc
i6 'ENr > E_'{q,- r
X snows'+-T e4l4"t
ffii?m'dvudry{+) 9,- ( { clon nfr'rg grk)
 ii
-I "hjD
'
.r- , *{t arygb -ld*t
F
F 'F
*cHz.,*NH
-r.iq 2 *NR, , -N Hs > -Noz)
*ct >lgr > I
-c=N 2 - coo H >'P>
-CIR 2
*01-l >-c-.-cl1> -_NlJ2
-c$244t
-@ > -- cr-t -- Lt42- >+l . +T, 4 Sizeoparryl, (rrtt<,i"n,,cry<Af

-) 2's , .fT d, bmnchinS-

#, rs 0 ft € t ,
EN st" + 2'TS c {49
-c
z-\tt*tvb 7 - t'-t't
*? C "t }'Lf cHs
I
( (. y.q s I
Lah'on c b' I n d u eH
I
R PPI I c.H3 @@
iu@ , cnr+rl'>ct1t
d JI= ct|3
a sfah'{r'+q o$' caxbufron d-J cH3
I

@ C-arbanion d, +
d,fr
*v c(
t1 Catboqfreeru..t\cal
o.o
@ rr re
cHs '?o
o
cg*clb I dsatl2{cvg
ffu'd'r'c e*venX* ** w .lul*
@ o
gfretltl^ ol --r
+I ctlL*eH*cH;t\s , &*ufl'c*s)
@ ffa(i'c Atr lZ
Rz*Cvlz*ent<nr-F
re AU il'cJt
(frf,n
&1"* Lo ovt
7');*'n., "!;" v ,rri, , cH*-tio7 -"1,
c:flrLoofr 2
&
t,, La cH9
I
cu

&.
**" , ) tfiz:$1x+il'^ua|
cr4s^crlz-f,1 'nt]cl,*l:I'z-cootrt
o
b
g il ( *| * ov
%- c *o lt
"rr,
cl
I
.:
g tH= cH )
R €nt so 'aublt'c no'lu*f )
( *oL
99 CHq (
NHg
arn'lnc
..:
Corn baia ebr .1a-t .
Llz * )
cyl:,-c*l>*oH 3>z> I ) NHs
} - oY)
-l *ot-l q
cHz Ll"l
et4 3
I
I
ctls
tf. c
) &t3 NHs
s z7
c H:r I mchll
?>y7
CH3Jns-NH1 5 ettf *t 131 trti,:
 Re.1;r,nac otr fnelo1nen'a el{ent
o Complete,tyan16rr ardetocslizah,on of fi e- is ca'Lted Qesonanoe,
Cond)*lon V 0
o

c 7\ r- 7f ennlqflart on + Cfi, CH-EH cFle- tLHz:CH *t*,"1 t el7>-cH =cH*clf"*l2_

@ 'N6-@ "+ cH 2--

@
cH *C Hz ) &"<e
r A o
CD T cHz=cH -9rr,o Lttz=c/f *o@

@ Trno 4 a1Elz=-CH *ciA , -.ry, , CHz = cHli

CHa-=-cH *-q ;

*tU, , CHg * Ll'l =CH * Ltiz

o

@ x 0-a -) el'lz=eH

@ A 4.4 B q ,ff, ffi,

-B
@J9 v
( ul u ta d raa} R u o nali n1 s

@Ae-+
wag363oaa-.fu
4 .-"'o o -['
(-112 '- cH: CH> E['""':-' c'{:':"'Ck'J
d:
Cl"l z_, LH= cHz +)
t zl
/'a 6- d-
*r 4:) cl-lz- * --- f ct-t2"-:'cH'-'o l
\-l
Cl4 =^ CI
cH2-= sH
3
o & rI,F

CAz- *
@ -= lcu z_:::-' ,n:::CHz_ )
LH2- : cH -cH> <.--D CH
=-eH z
q 2l

r ct,
CH; + CX
Zt - LHz <-, th, -cH =-
cH z- L c Hz-

3
,
CFl3- Cll-CH=LHZ- E fcnt* 3u=-(H-=fr]
a

CllT-Cti-
uJ2l t"H-cn> €
Aarcz +-. o@ af - cYf
cHL =- c !at .t (J CHz-C =AH - I inr='_'"c":"o Hf
(
[.f,r- ru--f*dq
@
cH>
1
_-
!
u4 =o.e * cHs e) Cll = O *LHB V
CHz -
@ fr+ {--
e LH2-
uUr)
-CH -,-CH -
{
cHzc.)sf-, 3-
@
e.H L *C l{ =- L* H*
I
 cH2-.
e, (H2 = Ctl *c H ='C H --C 14 : CHz- 'L- rp1=(l*lg
.' *ctt--NHz
@ .,:.. @ @^@
e) H0 0[1-cr.l=Fr.lz @]B HO= CH Hz- )>3>1
e-) CH2=cH*U ?ur*"n .9 ,?r*fl *., l>z> 3
o a
e) q-d-o n R-8= s- H (*l -oFt t2L> 3
@
@
o) R *C =O P
q o
CHz-cH "=O

M (Soff)ert
rc €-f+ et
o -Yl a
+,"1
f _afi
=O
a
0
o o{
at
"
e- *J4+gvatnlnq
rel eashy
tlectron
L e* dunsi+y oy A'\
f {densifl of Ring
me la clt're ch'^q
cilP d't rec*4v'3
Jo
*Nol7-c=s12 @A*Pt
-,fr i'r-ffir, -NH 8' > -N n'> OO
pap.A

-o,.{ >
*oR ,*Nl-., -[-P. ) *o*U-R] oO

-Ph > -P 5el > o-tgr* f >-ru o

'c a'tjo n oI M e go rn e11' L
1
r+ ?P

d -.fn_
o s+aaicihJ rb- Cavbacuh'0fi
Larbanion u
rf1
d ff):
--
@ -lt ,r +fft
C,avb n$eevad,ico-L d, +$L
@ o

(n Acr'd.r'c str eL-Yr^ -$1

@ Easf c stv '4 ttry l

/_l{l
@
&trt-l _r, * 4-
(fr> .l)L73
CH^
,.2 =(.t-l r:.\-J3- cH> 3H-=LYl<LHt4,
tPuo +L *L
_q C)-s, UE \> 2>l
e_ 7>z2l
,z z-
D,ffi"
o_
ry & @a z>t 73
 qH dt

/t
C, o tl @ r-t @ H tl
@ 1--) 1---9 sRs =E- f-
4 <-)
\-/
o t-
e H> Ulz- oo.u.
U o e
-l
e--,
o @ Hz
f,R(
q
@ 2^ L
{.---, @ +--) e a4 rRS 7

o Ut- 'L|1u & 2-

o CHz L

e.(!
tl-

#
d u *-1
6 J*.I 1d)
cl.
dt
lf,*
l{ o - l"l -H
6t
F-> SRI ?" f*
B, <-, 4 u---+

I I
6r

o t--5 6j:
4
-lA "-''% b e & -,
t
6-
r*
o Resonoli*+ sby ore h3Potheh'ca-L
d 6-
onrS nuono0n ahtlbti^cl f i Yeal'
)'n03*
" Relonanco bqroa'u'Hnnorc
intl ('g'+r'
Sfable fhan

" Dtr.o-fo Relonqntu por#al d'uf,lebond

OCCurs.So, th,t bond t"nttt liu
bl", Sln la I dauble bon4 '

-T*-
C- c i l'Sq Ra
o
R21o -- l.Zq fr C c

C=f + l'3t{ 4o
S+*bJt'+y o R'S
+
> CHf, CH: CH-O
6lt^f CHz=cH;tH=O
o fi,r-e P i bond morr. S*eble R.s ,

&t,@*
@ Ogtel.oarnplele tr tr '/'
t' o, \
e> cH3*[* cH>
o
,r,
@ Xeu*ra-f tt tt "@|
cH?-
@ *ve chayt on Elora
ft m or€ '
tt ' &) u491 =ti
J &- -ve ,hg,1e 'ghoirl'l oat*
be clns&
{'t t -'l)
0) cl-z4H-44*LH:LHz: cl'l 'clJ - 6;)
r{ L'/
6 ) a.+fe CHz=CH,- (f1'=-tH - CH=IH * LH3v
I
L^ X fippori t<, $lvn {navt dotev'lgw'r'!WP' A>t (aro'*h'')
@ *wve coolv'fr^h'on t'J rfi'ort'.d'lablr
@ to' E*t'r"fu^6^*'"'4 qmriafjc frrnorr lk*lk, @ ls'neor &,U1yl/lrr, rwufuk-Wcw'
 &

o
"p-
n<\
12 a
c- * r-H3*(1.1 *NOs_
/41
j YtlUNo > C-H LH z:-NCI z- | >tt t> tt

0. U1>= CH
- tH, p Cn,z-=
,
cn D
s\.
CH': CH- CH -_e H =_CHu 3>t
o
o
&
2>1>3
o tl
g bmfire fru'die sff r.E*ou6'
vyL
R.-[ *a*
2E RS
Reso

ry- C-ornpare A fY €.0lrl

q>b

He-
2>321
g Confrvt ksic sfr
HD-

llz- @
ow
o @ Hu
3>271

3>u I

OtaL Ol
HuPd'$n 'on
:
@ , @, Piuun4
t's i'LgW
I

r ele*nn to'r,ardt
c*H bond
*#;fr{rry"L'ht.
@Lep*r{? eH>4?yi
Irr. i l- cF = LH z-
\ ---' cHz(cH7l ' 3ou
3da @ ili--'
rl t3/
eFl> I
H
CFlz= f,-'
n- L TcHr CHz=eM-
;.-' I
LI
h
cho =x
T
'o CH, _I-,, ,,
c = L?l * t-H>
I
H
LHz- - 't
fic er-:14
a
tll*tbl2,
f*n llz =
I
h-C = tt H

'l Y-)o o dHz na D H, c ltr

h
m}fe dn l4orr S kb;uh!,
 " 41a5r'[t'1.1 olg Arboution 4 more dH 4 more'tt+.blQ
d Cavboufveek'nd"&)
*' 7' - te

4 ,1 -1 ,9
a)*en! ' ' '
fll.' -rh HJ dno6eno'h^an 4 HoHa oY
"{
e)Wr1, no ofi-dH
S+abi,'hl

&
cwg
c t4z._ c;H@ ) c t4s.- t rb-(p > ctle@
cHs -J@ l
2
+1cL
cl-.13
sa o4
qd 6d
@
Cl4z,
cns
3 2
@
(a C
/
,?
ilB\CH- 9^ > ,oor-"ff
/ cry_
& cHs-tfi> cA9 cHs O*
Z)" td\
94
c$v eH3- cH>, 7 LHz,
*1, cnr* c,H )
& hsc-
I
)
ctl g
w
CHo-= cHz
e- Ctl"9
t|H =cH >-

od
3\ (t1B cttg LHg ll
cH3 ,n ,1

0.,
Ctlg r-
C=c
ug
cHs
)
04;
c=c'
*H
_cye
) u4e

7'u 4eHs
tc
k
=L
h A
L* c*'v > 7=c
hh
Ctls
g4
h
b4
(d 9J, oe'
iza
Twns w
edra rY) e l-r 'c elJ u*
/'1
ts

ofi- 7f { o$mw.*i bond ln Pruen u of' fealeo t '

Cprallel'e" tmne{Y'r
* elec-*w tnen^e
+ele cFvorn err'c
ne*
tr e- ,6. ,n d't'rPle b on4
qre hransfurr<A *n *#af
alorn fo ,hnf"n reaq ,ent fu -lrch *.5ort
fte-{< at*a}rched,
u
clo nrf 1 n4" a tlaktu4
"
Ur,*@ -
cnDilH> - ) CH>* a[>-E o* - nlc )r--o
I
 r
g -q tnf
G @ !4qbi qr G
trr\a- \,\
0- :
4)9211
t t1
L LL \, o.rrg
5
€ 6 o
.\}\
(\,, \*\r- I

r>>)s>+
@
t 1- cI t+rs o
o
6 o \\,
t{ \.$ 1-
\ >t>t)+
G \-\o 2-
s\or-
6 t\o
L e. t-
@ 2-
\> \) +) 2-
o\
\
* A\nq-' cr-r-id-t" e.
bH b Yl \H \
o \t\ 3, 4)r) K>'l

\s e{\ r\
\\ t
\tt>
&*." s
.ts rJa r- \)r-)1)+
@
a.r? 0'2-

E
bn
$o1-
\\
$12-
Y\

s 5> \ >1-) +

lr{H \-!jt-t rstH \-Ls T

@ q rlr-7i;$r
\\rr-
\r. 4
t\ ,\I\!1 \r{ v1
B \\o.)- \> i> L.) +
Nt.
$'{\-tn.t
orb
\DOH \s\ Y1 \AS \1
o ot-I.\s rsh t> L)4)S
t^r trlrO
ko** rt\5
h
\-\b \ tAo\
@ \.lr\g \.}\ \\ \l! \
r> t) z)3
S{\-li.O
\g
3
ats \:S tul--\o.+q [-o-r51\ t-

$qr- \\\r_
$""
Not- \9- $"'
\'a oHt1
+> 1)r> 1
 $t\.u *\\l-
$l $r- rN\ t---
L>i>
ssQ
d: Nr- e*u
G 4> I

N\ t- d\r- N\ r- \\\
t)^. s L
tr\g 3>L>+> 1

slP $
\Q. $\q
\6rMa $r \^Q \pzt\u
\\a- $\Q A-* Q" A
r%\ \y\
!r s- 6v[uo '

i
 m"..+-t c ftwnah' Anh 4roruq{rt
, clclic egch'c
&l Campfefe R^ar onqne, t'n alele e
4@+. : {24'saqt1 L
R" . Hueke l 's Qrrla , b Llfnr e: t
@h op
ttlnt, tr e* ' t4IT I rg tt€- r1$, lbttL
hfrft 6fi{rlox{r lvne] /''

ffatr gPatv t$f-e\'(

-.
r
eP' YPr 6l*'' eP'
W- l{o/l* Art,^ofi'6 r Lu { o P""vt.

@ e
-aa*
R fiwt*
0P

@
n.. c
& fle
/; eF

tAk
rbr ep
T

c
t fiY*
op

<\ ip **
c

a o|
Y ffr*-

tl

C
Y fr-"
oF

c
r 0q
Lh
o

c
Y frfr
eP

m
C
T t$
eP

pp6 $vot"r^h'c