PACE NO.

DATE : \ \
HALOAJJ<€Nt and HALoAREN€
"IS
e CH -Of- Cl, -4 Eth \iclene c\r)\oride
CL. (Some C · em d1ho\ ide .
•
~ Eth tene ch\orlde
1
CH2..- CH2. \S vic.ioo..Q
•
CL
CL
d,ho..O, de Cd if.. C)
C-X Bond
(!) A\1 He HoHde ~ i
,,,. I
I x 'A-·K~lho\ide) CH .::: CH-CH -C \..

© Benz lie h~t'cle ·

CH~-P BL1' B~~ oR-x b~,n

in H:2.0.
CH.s - 8r
CH~-I

t. R-CH -OH
No.CL, H Not use NaI
-J,
HCl, -t N R. bc.oi n 0- s t:ron O. A., O~td Ise
(insiiu)
I- into .T2 1'0 Hf.not
 + PC ls

G) lJsin thi on \ c-h\Ddde (SOC.1'2.) Dor -ze n '\, Prcce?s& _

SN i t
R- CH -OH + SOC! > R-CJ,t -Cl + SOi. t +- HCL
\J I
R-CL .
o 6

- Rxn \ and 2 olco hc,I in +ne e Lucas- re enl .

0 g·- oH -~ sirn \ sho kin ~il- h HCL.

L > Co nst . bcH in ~..,.:;, th lfB r.
1e\d R- I W\Q be obto..iinE-&. b -OH
➔ Gtood

wi th Na. k- I In 9S-% Acid~H3PD.t-)

I

s HudrocOS-bon p R~ Bromino.t r-. / Chlorino..i-" Cp - S-o)

I

~-t: s R.
hv CL• clon al o.tiock over
,~om~r
Gen ien e.
CQr, be +ntE- • ,, ( Ben2~I t ree r eid I co.O. is
31- r'ht)re stc.bte d~ do R~sononce)
Pe Alc.D .
o R'><n w,¼ JR. a)e, rP\lerstb[e U\t'e

+hc e O.A . ( HNO_; \·HO~) fo oxk l i se

f' • Fluro c:omfd
H1 0 !rY} dur1 () ttrlf ()W.
p~pa.red b~
+fl i~ rY\e f-h O tJ duQ. f:o hRs h. ffll Uhlfty
of.~ ~)
 . ..

:
8en2e, Oio.2onium Cn\oNde
N1Cl-
. r Rx.n
➔ \ \ en Am\ntt)
Gto-H e I monn R',(.n
11 Ba l2 - Gchiernonn Rm
C fl A\kenes "

•
., I,. EXQ .
A
H
I I o~ovn, kov ~ u.Oe .

• l ~ 8AR I

2 ROS ts~o.Qk
•

• cf H+.
' 13.c+ · 4 . Reorrcn e ,m\I~

I
\tc hnl e ~n n CQn be donQ.
s CN -biomosLt ctinam1de ').

CH 2 -C---
,

Cl,
CH~-c/

C.H - CH- CH ,__cH

I
OH

OH
 OATe: \ \

-> H Bo~~1on Ox\dotion

I a.) C c \; c \ n- te~ d, ~e b) roQu<l- ,~ Qcc ti Mor~ Ru.\
I c ) No c+ C- No reQ "ts~ n etT )en t .

d) \t ot\ows. .s n Qc\d,~on i~e rt+ and ctt.oched

. rem sor ne s, cle
OH-

CA R. .TR
'-' N
C S N'\ T~ s R
C H..3 H .(O .E') H -~- H
C ==- c
/ -....... !l ) H 0 H _,._ _ 0

t-

t") No C +1 N e r-ea rro n e rne nt .

d) tt
r ·-

PAG£:: NO.
DATE ;
\
--
..
\
- =::::::::::::
.;.

. ~
-)

• ,~~$ \-\QIOQ@n ExchQ nce

R-X + RQP
Rxn
\j
t<\ethod

~ R-P
•
'
...........

--
✓ + A°'X
.., (x~c~,8r-J (t-f~:iF\, CoP.2, Sbf\;, accom;us~d b~ this r~n--
. t~t:
.
' I -
-
-~
11!
... 0
\I Rnk~\ stetn Rxn
-
-
~·
,ti D~
R- C'H ..-'X + Na 'I - A
·-, R- C'Hi-I. + No.><( ~-)
j (x=-CQ.,Br')
C ?C~{1Q..
t -
...J'. D~n ~r~ DC~>.od •
I
I I
l
...
L,-· = I: Barodioe
I
Huncls diker Rxn
..... , or~f""'IC\\ .n a.\ku\ brnm\~ ~~ faH11 fired ~~!~~r ~
I \ I :/ I
I I

. I m~ 't ,e . R COONo • RCOOA c., e:k .

\.)
. .. II 0
11 CCI+
"... R-C' -OAq + Br_ ~ R-B r + ACt Ar-
Ia ~ - u \J - K€{1U 'X
f3r
..,j
,. ~~
~----
Ll;d
~
"'...
~- I • 'Product hos an.o_ \es9. co.o\oor,
I. R°'c\,'c 0-.Q M~c. hor,,'s. m
~e.

fl- I -

·-•- ~
 DATE : \ \

R- CH,.--x + Nue -4 n)dun t() -I 'X

SD~ b" ~ h
1 J
43
br td is~ d C .

I bJ C - x b on cl ti.'lBo..ll -= bond chc.wa.<ler - ResonoMe

I o.) d e\oco...Q,so&-,oo -ve cha e .

benzene . :. Ha\oorenes \es~ n?Qdlve ~o~~sSN R)(")

€.xom Nuc\eo hiltc

RCH ~N ( N ttr, \e) 100,c ")

R CH~C ( isonttrtle) Covo..Qei'\.i-

R CH2 -~02. ( N l ~ro) Covo.Qe.cl!

\ \ ,
Rtvl ")( R-~'
e
R -H
 PAGSNO. --
DATE:
\ \ -
-
- R-x o~ ·, ns.o\u b\e In li ,"\O .
--
- R- x hov~ -£Qrne d, ptl\eo
-
rnomQ V\_Q.
-
CCt+ < C H CI~ < CH~~ 2. .,<
I

C H.3 Ul CJJ') -
'--lJ O(_ I/No . ~ Cl~ m .
-
-
R~so nonce O(~ C Ao ~' \ hcJ) , ct.Q ) ·
I

tt) Subs tlhtl-,on nuc\t9 cph\ tic birno \eau\ ~ (gt0!1. ')
I '
I b ) Subs t1tt.tb\cn nudeo ph, \i c ~n,mo\ec.u \ ~ C.S~,)
I

I
Et 1m,nctionR ')..,,: Wh~n a ho\oq \KQt) € (._,.:)'iH, 8-
'
\
h4dro qen o&om \S ~ co',-\:-h ~\coh o\ i c s o\U t\ Or-,

.~
\ \)
kDH . t-netr e
\
\S ~
\ lfY>\f)
~ . c,.::q- n . Suon ~\ ,
1
m'1 oc&\o n
I
I

l is co\ l@c\ B - © \, m ·, ncdt, en .

I ;-;~ .
I

18 H I •

-C--C- ' 1.
➔ -c=C- +
\
B-H + X - -
1 1 t
X -

➔ ,--~
.,_. OtJSS \ b,Htu tJ) rM()~ &hon nn~ e,\ \ k~'tltl dt.tP_ .On -
\
'

ou0Ht1~1it I u
' '
~ '""Oii ~ .:M,,a ,~ I a{ - H e&onis, -H~ n Olr\ & --
-
\ I
olkctMl 1-~ 'MfJ>~t ~I -; ~ fl )t tt-tf>J •
I
" ~

f.
 Pf~~O.

DATE : \ \

➔ , d L h.oio •
tn en eno.ito n 'b"xn &h.Q. erred

r,o.

S• S~ ..
R <··.... M - Gt r, nClrd r~ en~ nN2..
Ce>vole nt 'bond,
~cHv e
On H ·+ coibon .
- ev&n \-\ () c.J).coh o\ca , arn'lnes ~ H droco.S-tbo n .
- II necessC()-i to avo\d t-roc e~ rno'tstu re G-t.R.
conv e.¥-8 r, ho.Q\des on .
I t\
I
+nee E'.W.
(:- N02') o.& oat-ht> ..
ond
'
"-\C~ 1'se reat¼\v1t
II ' ~Gt\(~
~°'--

NOi...
 PAG.E NO. -
DATE : \ \

" El<!?d ro h, \ic Subst'r~-ut,on Rxn .

Ott> m - s \i de o c.ti v1 ti n tea -,d i ~di f)
-> · due &o ~esono nce ~- deosi t 1'se rno--r-e o.¾-o-

en C-I; some c~ r~ rn ben2.er\.Q.

r··,.
I
o.s C 'l5E' to benZen Q.,
'~:-::--1- -4 h~\Dcn rene cccur 9\t)o)\ bu& re u,r-e
-- - t t__;:;___:___ ;;__..:..:....:.,_ ...:..:.:.:..;_=-. :;,;...;;___..:.. :::.____;:::;..: ::..;::,.;;:.;._.. .:~-,-_,;;;. .,;_.___
,;.-=-,-: ~--•
1
/ rno1re dms+i c c.cnd .

r-~c1~

c~ c~
Nitra+ tor) HNO
--->
Cone. Mt.SO~.
 c~

C: l, c~
tr
+ CH C - cJ

\
• Wurb f\ Hl Rxn. · No ir'I cl'?I el~rJ

C~CJ, ... 1 -1 II --"" HC:CH

C HI + 6
- ii

C.\.-l A I

·l
h~,V\S V\UM()h l I -\, rt,ceo~ G s()\\)(.()()t t n co\ rn VYl~OU
 Pr t y er- Br- t1 I
M'OI @0@~) ~ 19~
Br

t ·1 O"\t t
\i .
CJ},
(N\UO)
+ Par~>
-lt cn~s
Cd L
PAG:; NO.

DATE : \ \

~ c.o. CL, C l.
I 11 H H ➔•
CL-C -C-H :,. ➔

rn
Ch \o t o.Q. ~~ -C-~ \ CC\- -H
( tr, ch\ oro.Q oc..cd:_o..O de h"{ do. 0~ ' ),.

I C,C\3

• la ~-CH ')-c.Q
,
.
I I
• c_H c ~ lens(' t -hr,c-n\o'5o ~thDn e.
• I t t - T~ .hl o~c - !} .2 - 8 i s ( 4 - Chohrc

I"'

• Ullmann R..xn
Nuc \~o hil~c &tb st,t ut- ton A\k l Ha \ide C R- X;
 PAG::N O. O I
DATE . o.3 \ 0'8 \ 19

,S TrT UT I -R.xn

CH
r: - - C - - -c -
I
C
•

G ~cH -CH h--

All l L

2. Nu ~)~ le {N ~)
+ CL-
· No- R- C'l > No --R
. r3·· +- H -C l > (3- H + Cl.-
 p -

• ce
tn b

I ("')\'"'C:, ("'\f., r.' t, ( have low '-tem ()ro lure )

I I . I

•
•

, I

CH COO H ., Cl; COO - . .+ H+ l

•
Ac, d Co e
Bos e
➔
hov
• I

..
se > l . f

H-
.....
Cl) H {OH . • C
< RO .. ..
----· ROH
b) (_d) PhO > PhO H
- ------- ~ - -
 2

-tl - /

...2 ~~
____ ..,.,.___r______ · _/ ---"'ret_j__d-1...__ _ _ _ _1_--:._-:_-:.,l_ -__·/
- ---:-t-__r_. ,~ A f~ J.-J ~
I
1 - ,/

I S t'1 Gt Alorr)

Nu~
-
O;
-
Fr /
---- rJH - / t'4~ - ( /~ t'1o
~ - --- <,)

_ _ _....,. ~... j ___ ,~ H___:--'-~

----'~--r_____L~_____(____,_,::~~__L/_ - - - -
,
c/ r,Li
R@Gor,or)ce -
. -,,, .
7·

- I ,. /
.J

r, J ~ I /

~.,) -..
rfJ1 /7-s. . . ••
r / \.1 ·- 0
r- ~.~ r- •dz
~
/' (/
'-
'J-':r•
••
 ,f)ConjuQo.:\e base o~ ;,tronci - - - - - - : - ~1
ll 0. c:.1 d ts t()~C\ k. (J r, t.::>. 0 4
(. -- QAit_;: \ \

I'

\
• R-o . > No\- Possi b\e ..,
' H
R
-
cr---H
I+
) R-+ + H2: (0 ➔ Removo.l ~ ,..
H H2-.0, 1's ,.
'
Alk 1
OH >H 0 CB . N.) s •
~
~

. OH ... <. I~ ,O CL. Gt . Ab'i\',r )

l
\
. . I~
I L.G.A
I I

2. OH- <.. H O ( l1- )

'3.I CH -C-0 - < cr:-c-a·- C-11-1

I ~ II .
a 11
0 \
4.1 R H
0

c~- s -o- < CF~~ -S - 0 - ( - t i - )

0
4.
• r
co 0

rt
ioni -zot n t

➔ dime th l form rn· e

~ d,m~ th l Ac~~am,cL.
~ H~xorn~th L
Phos horom ,c1.
 S lotn
R.D.3

""(

't I . .
I CHARACIERI.S:T\C-S ~
II
,.!I Roi@= k [RL] 7

II .·. e, rd <!'r == I •' . S N 1

'2 . I RQ:l:@ is clin\>d h-i propar'ti coal .\.a
I .stab'! Ii t y cf c~rbJ c o±i ao •
..s.l R.:!?arcan5em@ol o•f carboccdioo Is ·,

4. Polar -prol ic: .so\vl!'>n:\: ls used, CH.z.O ,Ro,-t)

\ @/2 :nuc\Pcph'dg Qr cond&nso.¼ion ~

I 'nUc.leophl I~
~.I lcJ heo \So\vent '-Stor±s
So
 PAG2No. ol
DATE : \ \

IJ pol or: prot \c ..& o\ yE?0t,

r ?,I SN, al£c ~ \Ve J,b::,reoseled-ive rxo .
I Ph Ph pt,.-,
H---Cl H --+-- C ~ 4- ri O --+-- H

~----.----ttlI-,f -ch_1_ro_\_ co_<S'_b_o_n_ p_r_o _d_u_t l_ 1_o_,r_m_

I
&-h.Q.n
_ __we _ _~_e_t-_ _ __

roce

t o o ..
0 I SN -'> 3 > bEO'Z \ > ~ >- \ •

> 3 °~ "meth Q ~ci.O.et. · a..o_do.. stable ho lL

BenzL1I so..o_ bki
 ~ 03'
\ \

+ R- L -~> No -R ----- L

.-- L -~'> Nu -
I tf!
' z
/)<. (Tri on u\ar b'1
u-c

z
xn

I C1-1ARAC

r. I Ratt9 = k R-L No
y -= 2
2· Rah) ..1s de penden±
th
 0
0ui °t \-\°'Oe~ ',n V. P - p- ts .,ss b"-o,e.J)\. No,.._ l Vop\1wi P)
,

3. No corboc~'on foY-m~"or, and no

R-T >R-Br >R-cl >R-~ (L.G,.A

drn?

<;

6u\k ne~s
\ /b lkun@s ... ~ "Ir z
l
,xn.
\
~- ers1 On
9. CH3
~
~

H Cl +OH > CH H + Cl~-

fl)
D