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o pigdro c,,v_bon ds a-Lsa wded {"r raen".f" a*-are o $, PetS{y1et-s

ex l- eYhen e, Pol 9 P*P*' P'lY sQ rew-


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Sa*eirc.ted Unsc'l-u rcuF'd firumah'c


nn u-tfi'f lebonQ d \t d^ a tr',9 d toc axbor
C.*c o*nc{ C-14 C-C r;,fi.eri"fng d)erna*e
C=C
Slngle bencl od 'Sioq lt onU dou-ble
c=c rrnls A haung
QlKan t OY
f4n * 2)^ e)e ctYoa '
open cb c*{''} 8 C -c sf ry lel>end teo bh
C n !-1 zni-Z i*5&lj(clrl

ct"oo.lJ<ane
c-c doubleWnd
Q err l-121
cloged chcuni, e-c Si n1le lrand

W, '+ a^LKg ri e
c-*c taple bond
LoHzn^z
q tka-n e
? CnHzn+L
. pqrct.ffi-r'n [te,x r(a,*l,r)
found dn
o LYl4 + firsf rne rrrlbet,u rrrelhan e i CDelmfqu I rnarthg ptatet
,n ,sp3 hybn'etizq|-isy1 (r"y.4 edril) 4 laql'so
:n

C*C c* 14

oV erl aP sf -+b *z- s


tsond Lq^lth t,t4 A o l.lt> A'
8o-Ss ?G)
qt'b Y\AL
Bon{
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q"nsrd rnefhods D Pref: qYa.h o n


nahbn
Frorn Un Ya* ( hg Ca
1$/ z Ree; c
tww) NCrel
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@ Soda
x lahbn
CavU o eau kolbels ecfrottr,
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2';"73f;#[,jlj:'fr',
S unsafu recl H,gdrocorbon H,
Dr
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+ HI
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@ "t'k6- hatu'd-o hluY'tz- LYfi
CoYu1 house SYnther fs
Fr*n kland Qeac'trbn

Soc{a -Urne d e cqrboxY'{'ah'oo


@ Cqrbor ic q q'd
korbe, elec* *tf

@ nard --7. B01 , HCI11, R;sH-B


Req U^r +-t,
(,Drnooun{ h *'n3
q .h'u. hy dro leh '
hr'gb sY cJJ<enes "

.---) aJJ<6X h"Li&4* -


R-yl ?-x + &t
Red P}HI
q 6dr@acr'd de# vnflve, ctlHant
alcoh pl, a-{d ehg dr, Kelatw, ewba1;,U e f -ro'c
@
alden?drl l<efo*t P
ruolfi' Irr'shner Re4utl'on
@ <--rJ Clernrnensen kduch'oo
Fro nt U n sc*u ra.Led dwcaYbarl
@
t Ranaf i
C=C
Hz I Pd P C- C
L
OY

CZ C

t. i ruf (' n
e c =c 2 o0c Sab.rtfer s > ardeYen'g rY

pf
L 4 .,;ii
0
Zne -) Poutdevform
n

.F Nqo H -, N"
I
?unq sl -4 X l/nt

o M@'-' ioq'nob forrrlad'


rel a e/
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r's af olr .dT(t3'"
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npno*lo\
e s
he h
.V

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l'x ea,l-
hyd 4*tn H
e
sffi}trffi r) a,
' c{g*cHs
f..t I
Fb, Pd,RA

y Flzc ch-l> 2,aa'c l'oorntemb

il l' H>- c't4 >*'(H3


?L Pd, e
frz t'.1

G-x CHg"_ cH = cHz >0 o'e Y6t WP


P(r ?d,?ana4fli tHg *c\t-Lfr3
Q.l-t rti
rDaffl l<rq
v - (-=L -H
I
3 ffiL
h

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frorfi alk hcl)t'dx
Reduch'on o alk baHa-t

C zn & Hcl (rn aq'd )


6 zn v cFt3::- 1fl J.L
l-lL

R-X + 11* *1 'P--Fl + H **X

HI ilr*, "f-Hz %?n


@ RedP + Ftcl
.l-
@ Li rtr t 144 Zf"l,H'i tzH
C2ll5Ll f Hz , o

o Zn -Cu eou]>le in c*.0!{


,) ,, c$3cv;ct1r-ct JW
J
Hcl

@ Ar - l+1 )t
I+H> env'dHz'cw
+Hcl
*X
' 2fn olc R a R-R t zNafi
-'X + PNq +
B" Llhev
R
r Pree v-qdr'c al ln lerrn edia-t e '

I Ht3 her 8 Sq rnfnefri'ea"l ilRane't QYe forrned'


L- @E@oq
auult" the flurnber o{* d-tJ<;lf, hal-r'Ce +a"YLn
u
are
" L0hefl boHa dkqL ha.b'd e-L qre di ffere ot , then ?,P* fovooo
nu mofC.
*a, uouYt z ils noob Autrtable nrttho4 fo v alXan* oh odd
Czl{s T .f- cH3L N C: Hs-(2 l-lg
'r\Je.fu(V
"{ cfl3 *c H3
(2fi r *cfl3
. aeH3BY .f- )Nq fW c?t3*cn" f z NqBr

" gceHrbY +- &rrre * *, caHs -c2uv * tt

l"
rrtale Na I n dzrX elher3l*ru
ry 2 rnole-'r o5 iso pucpU! chlor.'":-p' u:rtb 2-

1S -'dtLtelheY
) ---'--t
f cH3 -ln 'cH3 ;2 NQ
LHZ- tI -*cfl3 LHz* cf *tt4s
t-lh * ttl * er)3 ciJs * c[4 * ct43
$ Llq gh iso Prapf chlo?n'd-s g etbt+lchlon'dl
(j
ore LaJ<en ary'frX No e dn1 el-tu^.
@
cl-l 3* cH2.-Ll
LHg-cH-cH3
CI t

cH3- ajn * t4g Cl-t3 -CH 2c

6
LJ- *iHZ
* Cl'i 9 eHs*cH z*Ulz-<Hg al c H
CHz*
Crr a - Cl"l
eH 2 - c-HS
H3*Cl"l
I
Cfr3 b,*aru
z-l
C
t3 -
Z'melt'$ bulanc"
z, 3'- cU
r "fnJl b".J-eff-
r TAT) k lart 4 Rea ch 'ort
Dry B- a + 7ny,2-
X +ZN +X
R etbe r
R

B-/
Qrzn + znXz
FranKland renjen+

G,u,[
70 Qus -czHs
&, Ca Ff g -cl dvrl e-+ner
Cor *hou.s e - nlnesls
a L;d,ed Ya*lon off,dKonex .r,nlaini add r'to ofi^ Cotbon '
$or Pn"P^ w R t
R-x Li
cutr
R*CU-Li
ld R
-x R-p '
Ufhiuqcb'alr# L>PP*Y +
r efih R*cu
&/lrnan's
+
c-o) Lf-x
80 canbanrbn

rban fon lnftrnn"


il^Ie
Bhalp hr.l.s * lervs sk nlc
a CA crawdgn, e
o N hdid.!"

4€A,f@€:_q€agg
8u-e clJa *cH z-cl Lf C'llg*cllz *CH3 + Li*Ll
@ cru @
t @ cl-13 - cl
c,lz-nP
rbax fru'
C,-ut1icsodr pO oh
o-h'on @
a *Ume Dcca r-b olt
a$ N o/ t".
C4 o
QricrUrn"
t'arb axyt^'c a,ed sd*
. Salu raled r:filno
o
ll :-
R
+-
c -a
p1a ol{
R-tt
NCI t-Go t A
t
NQz La\
(' etarb o*Alah'an e

e ?v rc w ofr* re-nn c' v 0


bu'I add i-l
6 Rerno Ya "* Lo al4 q""+ 2
recscFant
rned I'g ofie g2rbcn less tbfrn
a a))<an e for
te'athbn
" hte? dcwn rf,ned)'te' R*fe obd, "'#;il n
o Co rbanlo n lnte , T-CI lqtia

a N4 oH cao Hz f NqzLob
&tr{
€- *0
NA,
..L
gas
H- J' A
ct-te c) eLarbaxy la)ion*e HYdraSen
Aodt, wm,farm -,
o Cac 1* NOz La 3
*J-d *o
.f OH ct4 4
-g-rll Cl-ia A

* r11€thgne, Car\be ?'"1'o'ed"


t ihtu,lLoarly,{*QreP,-el.ltonl;a..fi)eLarbona-fam
9{mpl9 bq hea*lng '
-
*hen decarboxfatian ocrtlrs
- ( -aol4
L CHg*LaoH * Loz*
cHz{coo H

b e Ceu) e*
a
etl
Cfr{bio't1 {on CHz*c *oH
J onan L Q -)
Qes
)Sto_r, e
oYdetr 0f f"lloi^tln1-:*
&un Qivea +ha Yee c+, " i+Y CH =-1- LooH
c|z -- cVl* Lo a H
cflg-eH2-coDtl
cH3 * cq2..
a , CH 2=cH
cy1-=P

e>b7c
-=
!)l Kolb s e)ec4,*al rk
"t
Adt
eleclro [7's rls o$' Sa.tu rqted
:rnanoCavbaxyt) a aa'dno fi-
\i
t\ Wnfurn.I>o
l b
ll' ,l!<rfrolY*Q, R-e l&lo, t&Nqun *lt:
&" R* (,- oNa Crr*hodt '
fr
.. ..

-ele*lwl#sl;) ceHi'-c* H! +aLo t e NqoH 4-H2-


&CaHs-c'oNa anoA* b* odL

rnechanbrn q+
(' bYeak fntu
Hz0 *. ep H5( o 0* +aN Z'clnS lt{)
2 Csl-lsr codNat electml7t r'e 1 6alr{ r
C fonic rornPct)

eil anodt ( t) 4 Hs +,C-A L


I ezfiS* C-o*
Ca

'?. CPHstoCI
J rq ca Hs | LoY
c:Hs *
^a
A o* t'S'tc*eO bi
+ e '6gg6d),
C -U
if
o C2fl5*C1tl5
+ >1fl z-
o
ala,fi 5 coo

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.) f+ H
l")
Z?
a'tta d*fi of vl2 c,yfk&+tr'
te*
'Nq
N
Y,
NcrO +
rf

2 Na'
J.
.l* z €* *-a2N o
*l-12
2 Nq + f-lzO -i zNcl0H T

+ Fucoo Nq R *R ; g'r-B'l l- Rt*Ptt


+ LLsz + :_Nqo 6
lHz

n Ftree Ra;5'cot @'tnL(Y"YmeiloJe


o Pt-l g61u-h'on intrea''u CNc{ol-t {a** "*r*1
"b
p rnethane Co-dt be pre
f,ared,
rt f,'aYd @

g r t-o.lre acfive hg{rcgen I f" r{nS oJkarw''


-fi)*O-H *+ Q-l-f 't- -s/l'o
R M oL -*X + m4'*lo.-
{ u--
-
-&f)- o-R --, R-H +
R
* R*r-r + me{JH.-a
i 1) -NH.-
n'{ n 0 0 [ a th've H ud rogen t't)
. T}rrs rn et-hod is u:'ed r'o $l
c-ornpot-tne] 'Lrrr€ L-Jifi n'"f+t'
meFh*d)

*1 hfifwn alk^nl
G'R Reqcl -+ a*Yl h&U'"Lr
@ x
R r"t x +P-lx *--)R-Rr +n1 -;x
so_
&
p r-V*s

c au'd
alwhol oJd eh d,othafaru' B Aarbox
R.ea uclrbn
o
ked P,HT
oc
lso
P R.-H + Hzo + Tz*
8-0 H ir-H I, lf0 L

+ ,t ,+- &,'l
,) A.-cH3
R*ctlo 4HI
0
11 l- 2"r,
R-J.-al R-c rlr*Rt +
4Hr
o
*$rr
z +
tt
Q -I-orl B,*cfr
a n'r "l/ AL
h
,A
Q- E *e1
q_eH3 Red P
6HL Te{n,vu T>{or{n(4 f n
0 t-h( rro ,

R-N-oE+
k-tHg
6Hr 2,P +8Tz
-&Ptt
ddeh1 ds'kelont
crlol[' Kr'shn€r vedn
o I gdroz'nc
H.. )t
ll O NHz - NHr- eLLkany.,

,/c\ /cy
@ koH

gf emrn eqslq QzaT


H
a
zD?.14 g
v eLF arL{
I I Hcl
,/t\
,zc \ @

ph coL pro7ertt1

(i )
Cr* Cq u &* !*.-i

ir' C5 "- cr+ lr'q

urhi te- sol id


7Crc LilatY

o f)€o PAtane v* Wqxof,Lt 1 lwh*a"rt o


*'f ?e*aqv<
tif ,r 8.P. o{ f,notecrr-{-wt
b"P" ol .n - penhan e 7 s aperrtatte >
I
neo
F"W
no of Srlde *ain
o0r
rl3 ev)'en 'n a af" LqYbc{t a.lam Lva rncr€-
0r) [0,1. P -a aJJ;<arne-r 1', o-ur i

r"'1 P" than its ne\hbCILtYs,. ]1


du e ta 5 g rnrn e*{Y
.b

Packin3 e-Wid"tYg f
|.

[!v) a).V.anex a,nx{ttert f n nature bec&u e-


attd c *H -Siqma boads 5'{'- g+Yafiq
r I henuda nat
C*C A bre-qL
eaA4ld.

@ s C*I'l So, thu) sre- non.-polQr ,


A€n: o A€nY a
U
vanderugq"ll {o"*
La)
fi esotl't pvtnltc
oht fhe rnt'c
€ Xo
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O sabsgfr,H,n lodr aatlon endo*hevm
r'c,

Nitrahbn
SuJ,Pnonuh'"fi
fleoc h'o
onoJt'ofi (ee"d
Ch[oroS uj-l;,h

@ Co*b{r-r h'oa'l
ii
i
axidah'ort
f
@dW
lsorneYt zoit'on
I

p5ml3xf s
"\

@ flerchon u'r'Fh sl<-onn'


Hal ena'h'or)
,fr hatngen a

Hgdrog en f** a)Xa-ne t' s'rLV taced


+ Ny
Lr- R-X + H x
@-H
Real ent I uY tA^-
h'F a
te'^n P L eso '- u
sa c-)

Percrr'd* * x:': [clr ar") g'H >t'H > l"H


a}lrnr," o
a Reac*r'-rr'lq o[ HYdo'9 en TD,
te en e , XT
t; lg- 7 f4rz2 reat
o not
o e, hcr-Lo3 at v-sm t:e
9 very Slor
Tp1$.e,verx aPeul.rslat
f n darl< -aoxfdl:J,g \
f iioa I l",NI
, Frce rc1c{r'e rul a-nechanrlrn sE {nvalvea 3 gtep<
r) cl,a-rn@ n ih' I

z) C-1.*rq d P
!.

n @ Termr n a)rio
n
z) CXaJ

Chlo rirta,h'on
,
CVla * cl z h L$-- CH3c
I
C,l2. . CNl2cl2
l)f
c+tc,*#
l*" tcl q
-.4
h&
i
6 uoa W a,n+ cH gct (rnalov pteaur*)
eH4
(exee s e;

endo lhermic)
cha"rn in i h''a#at} (
hJ c
a
+ c,
a

I
e
-cl honolyole

a*h'a n
Chc,r-in

cr) ,n CFl4 +Cl ' [q-cL{3 lHcl


' l-13' a*fucKS 0n Secand rndl eu.b of
C:
chlarlne ttt form lsel
g clo
cl-cl h*- CHvc I *ct
___7
ta

b)
I

cH; 't-

it selft crnd proc)"u*- I'q .{ar* .-ul


fi sLeP (b) repeaJ_.s
SteF (a)
'pw nar.,o6hqe4 hKF*,
roer* LkL{A trn ,l*L
o a
C l-lg +c I eH2_cl +

LHzcl
o
+ c cl '-)
c
C- hajn *erryi na'*t'ott ( ero lherrni )
cHJ
a
,+c i ---, c HO*ct
{,
eHj + eHj cifl,g*cH
--1
et' .+- Ct' €7 cl*cl
I f-CI rn l'nafr'sn @
cblord'nafr'on B brominah'an are Ba'rtts "

Flttorlna,fi'on
( nrgbtg ex lctosiv e)
er* f))
o Io' ablain P* d'uc*t ue- u'ged Nz 3a; Cdn
Nzg ao c+te| + H tr
cH4 4- Fz
t
I 6 di nah'o t1

cH+ l rz + c il.'r ''- [-r L


HE + *rlrR, u*,rr;-+Hz-o
n ob Ox tbl'z-r'"* o4u*
" Cavried ot'.}_ I Prexn* frtou
F >-*
'Ul!A-
f, , c13cl
gt/-[. CFlq + clz -h
e,lLU,A
h# Ccl.l
cH+ + Ll>
---l
"

q91a'A

l-l enalion oI hl3 bef aL(o,rles

eHa -CHz*cHs
cl
cHg- c{z* Lr42- cl "1- cl'J3 -CH
*cFls
h&
CI
IoH = J- Y." 7?. '/, = 27,
o
fl'H = B.B /\, q produc* z" yrodutL
fu=H'-r-E
/o: l'Fl x-t loo f zottx a.g
toH,x, ta 'Hlt,3'8
JHv l+tHx3'e*dHxv'r
6 xl lsu
6rt*4x3.8+o
t trusy, Yss7.
6wvi'ar)
Lfrs-tH -LW _cH -(llfrl 1t
-!L---)
h\}
cH_7
I
cHS
Cflg* c-cHs
ct-13
"lHs
ro 3nO
'lo l{ x, r[w v'f
'/, = ghx 9'S fr, 3'H x
13.5
t6CI

l"pxl + 2oH x3 8+
I xV'$ t6]0
qy'l xl@ l
13'{
q.s
4xl4*o+tX
t 3'g
.1- xlou
,i.s
ry 3s/.
ry6S /,
lrnaj or )

chlorlnahbn *' non gelec'h've


g orzi>1")
bffDmlna*r'orr -> S elecH ve- [ CI

Clz *cH2* tl I

Ll43 * ct4 *cilg


cHg *cl4 +
CHs *CH -CHs h*
I
cvlg
I cH3
cHs
\ I no"$r)
N itva*',:n

[ q o0 - t',-ro"c )
{ 3
H r'gh E*? :

a n/tm'c qoid ( Hr'rog) 1 Qeoa"r't"


Hudxrqen ls rE-.blarrd bq Noz' n C*c bond eleua'9e
pbssible nitrootXanet Qye- f-ovmed />
6

a att \,
c*,", ?uod cler6%.,
o
fo"2 vad.tcal 6rrSs-#W'aF)'
Yo^,fu c cFlS- C*l L*N 02
eHB *s H3 + 'H NOB
CHZ* F[o]

*cfr>-LH3 + Flt't03 4{a c CH3 * c{z- CH 2N 0z


CHg

cvl 3 _cl-l - tH3


I
t-tor

oz-
CH Z*cHs*N
CFla Noz

on
v . H l'3 h fernp Ltl m'e )
o[5 sasf bnLl-l'soq)
' R.err.ler,* ) Oletrrn H>lzo + (mi,xlure
' Hyd*3en t's repla ed bg - So3H. c
Z'H)
fr Loaet bra''rtehed
" OJka,rx haptn 6 ov [noYQ' tsrbon
fflvct Au"hha ylafiton '
c*c- c- c- LHs + l-f zsio ? C*c _L*c-c*6*Sog14
HzC-
or
Fq rninp l-l2s0t4 Cvlt
U
Cl+s I

e+V-L-vl + t, u,-b.-I
so3'd
I cHs
cit -d
veac\ uri fh t d7

, ?Wl'&* ,buul-arr-n ,Perufa-n-n- 'ag


1ou"l e,t* alXane,a q t,r'd
9 ulpl,r.orar'c
r.ir

vnpOu{ Phase ta}


P*^
gagH
e3 H6 1-SoB C
3 H+
Chloro S o*ion
( Re.a Rea o n)

*ob hl^
I

** Re^ lznt ts n, F clo ) tn P


't
:'. l-.'\ .r l :].1
h# C.:HfSozcl + t{e-[
.

C3Hg {. S0z*clY

H>a
I
C3 ll +SosH
' u'd)
Csorph o n l'"ia

Cnmbush'on

,i

,1..
. .-l

I
Cnrn be**hon

Comp lele bmbuahbn ', Cn H zn12 * [?:xIJ, 2- .*4ncCIz{n *r)Hzo


" CHytg) +2Dzta) LozCSq)
-J * ZHzo(r),
'AH -Ve
=

' €ta rffl,


Cq Ht o Lj) +JZaz b) ) 1 Lozc,g) * S tiz3 A H = -ve
tncompl ele CoYnbu,t Hor, *tea*o
cowiF*+o,
c H4Lil\- ca B) C(s) + 2-1420 (e)
Carban
btatJ*

Heal. o Combwt'Hon

Hoe d n, oh Cavboo
esFlB,2 (>He ) (Fll

@ goc4 l
Br-o noltlnq of alkarur Cws
t
c t4e
> Hrc -i-
c-Vs
"c
H3

(g vlo c a4
J

Size o ly "l'l'\g
LOn trolled ox r'dafi'sn
!
oxld d

o
a) unol
fr tt<one :

aldeh y4*
o xd n
€av6oxJ Lrtc c(tr'd il r

Re"l hot Cu or ktuhe


cH 4+ 02
I o oo*rn,S2g K
cHa 0,*,
aleoha I

@No2Ca
CH+ + oy
A
HcH 0
r ! ,' '

ald ehyd:
o
Mn Hs Lo ,)z
eHB -CHJ # 02- el-13*! - aH
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