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Haloalkane and Haloarenes
Haloalkane and Haloarenes
Arby an
Haloatkeonre
x
TUPAC name >
> ne propys bramicte Ceommon)
|= Brome propane, (TO PAC)
Bre
C-c-c - Br
a 2 | Y.
C-CHE Mo prepyd branwole
or
2- Bromopropane
Meeopensy Chto,
; or
Cc | -chloro -2,2- dimerhyh propane.
q3s 2) mal,
CHeHCH SH See Retyh ChE
ox
2- cChorobutan, |nu 1 =
Cig e Chee 3 Vinytaltorel / chtorntrene
t ud
CHECHO te 3 Ally Ctericke / 3 -CALoreprop-|-ene,
Chu ahlaneks
a Cy Patrylanr
Diohtoronntnare
CHU —3 CMowjorm ] Trerlove ©
CH Bry 2 Bromojorm | Trbromomethane
Cig 3 Todojorm | TWiodametnane
Clg 3 Carbon Tehachloncle / Tetra chlorort an’
Naming of Bry haliclt 3
hye Kote | Heoburaine
ne — > Bomoba : é
rome | be bromo
ae’ 6 _ o]m)p
Br A bromobenethe
Br
2G, 0 CHorvtobuene | 2 - erterot Quatre
Vy No ae
Hg I-Chior-2- metry benzene,
Chu Ben Clemo,
Ly, o
C Moro p habe methanecH ‘
(Cs), COM, CH CBr) Que (Cag=e?— cn, = CFP StL Gs
Cus Br
+ Bromp-3,3- emetiyk -|- phanglbu tans
ome
Doering rg Sr
CH CHC (CE) CHa CH CCH), D[CHZ = CHES = Eiig~ CH= CHB)
a CHy
J
B-chlova -s- wath dhere-2- tre
ee
1 _entorortys
Chay |
a
ls S35
Ci -e — Cis
CH3
2, rechimdhey prepy
mM-Ct Ci4_& Hep Cuy C CCitg) 9 3
|-ciMlorvomathyl-3-(2,2-clinciyprepgh )burzens
een
4 z20
UCH CECE BR, >
u Br
\-Brome-4-chtorobat2- gre4 uy
(cus), CU > ofa = era
La
Or ore
Ge po iment
15 1)),243,3,3-He prachters -2= Cte lorrnetnays) Pre pate
(CH) COM = CCH) hy TP CHa, U
D (Cig et ene? ]
r
| -cttore -1-C4-loctophanyh) -3,Folimuthyl but 1-th¢
———
FES) conte tre Stucae of HM potinadg apawic
halogen Campaund
O 2 = C2-Cloropheneyh) ~[-focdooctang,
i z 3 4 s 6 2 8
TPC Ha CH HC — Clty = Ca ~ CM, CH= CNG
© | bom MA Se Crbetey re metry brent
br
SCs
zZ
|
Ci —CH-CH- CHfeb Choad ee fotlawtyy erganehelogen Compasund
D Chez Cw CH CCHy) CH CGH)
¥ 2° carbery
CHy CH cH = +e] 2° (teen) aleye +t bok
Chy Qity
D(C Hady CHa CH CED Cor
ae carb
dt Chg
Tet cny-b-em
. Cty
NZ 2° Benzyhic hatiol
BD Chg cn cecaycu cH Cen),
Y vin opr?
CH; 4foree- Cty may ~CHy
a C hy
Vingdic Holic
“eer
@ Cig CHEECH ~CC BY) (015),
| rs
CR a
J, Kr
ava
wy i nse.
TAommm +
DO Chain Tsomercim a
Cg - CHy-C Hy Cll - By
Cg Cl —CNy By
!
Cig
@ Patthon Lromercim 9
Cltg CHa Ca ~ Br
Chg “CH &- &,
Cake betity
G3 jfrtoatkare and paloarhy are tyelubl wh Waly
a nea
PS Heloalkare, bay dorm Hg crogem bonds urtith Watley
Lene pew cetrrachon fore betuztn heloatkan anal
Wealtr molcul 4A weaker tran oraigthal Hy dre pr,
bond ty water Mokicuk » Herne Halocdicany ang
Anjalubee wn water -
% Morcousr yelrated Abtygy 44 Ley Hran required
dy
G3 Hetoctkane arg Saleh ain Organi. Aaluenr
Pos ‘Fhe pend thtutrmeliictar — athrachory, between
haat and Salus modrathis have Path Hae
Aarau strength o4 resmured to deParale —reloalkane
and feluertd matialy,Dipak Momenr
% DPipal momtnt 4} arg olipals 44
he Grd
Menee orcler cop olipale manny 44
RID PHD RUD RE
die te clecreabing or cten ey bond Lungin
b CHR 2 C-&D CHa > GE
& Nex cipal Momet 44 olehermied Ling. Vector
Ao Oo addition
Q3) br ,
set. ange He makicul ah ordir a} ctipaly movers
| Cay, CHs CO
[ae CHO D CHEK D CCG
Y
a ak OG a,
ae pete > oe
ue a > ue Na
QA He clipak mont *} Chtorobenrine 44 Later
tran thar oy Cgctotereyt crloricl
63> spe Mybrad Carbon SPS hybrid Carbon
Lb ¢-
7 Sha £
\=/5 L {
ley charge Prone, Charge
Speersbian porationi
{
|
4 AS C-atom tn eltorbenrwe 44 5p by bcliscal Agus
7
Me chorigahutty then spF ey omolited Carber,
of CqULorhenys, chlomde , lesy Chargyr S-2parrren
445 fourd An Chlore benrene Cy aleeraoues |)
Dat to regonare, C-C, fond an Crlordbeyrers
Alyure patel daubls bona Characky
Lon Hy
Aw bord Lirgth
= —
OF <> [*
Partial eae lees
oleterbee hovel bend
Uenu bond Angin (d) ok reany 4
As ts yr*raChow'eat Properties oh oh byt hotel
Nedure 4} C-¥ Rand 7
* Cre bond ave Palar diu te mow thictrontgabivty
G1 halogen ay Campared te Carbon
$t
—UL x6"
+ A AE + Aatoyen atom tnereasy > C—x bond
Anan Any casey
C-LD C-&D C-uUD C+
NuckeprUic, substtehon yeachon
RNa, Ft Ny, 3 RAY, Nu,
& An thie Ytathon one nucleophile ye placy
eter nuchophit
¢t 7C- =
y oi xt +z? —s C2 +
Subbed Huicheephiey pont
¢ Dery. “hatick) CNucleopheee)
x Des fo prdtence “4 PAPAL pawhice Charge on carb
atom pucleeplyly Can otack on elopon Aepiciienr
Carbon .¥ Stronger nuclopil replacy weaker nuchaphyee
which 24 quod Arauing Graup
oo
TKN) 5 Row + ke
Con) (akconat)
e
Nie of R-o-R' + hax
(oe (eh)
atc es Rot kx
R-x —] (Za) (ate ge ening
tt A4gcN RNe + Ayr
(cea Arorynicle)
R-o-N=0 + kX
(Atte. nite)
AN +t Agr
(n boat kane)
g=t-2 e+ Agr
(R Coo®) (Ester)
+ neds RH
Cy
TNs 4 Ram +Hr
' (1? amine)
TRINH pean ¢ HA
(22 amin )
RRRIN + HX
{R’amn)[es Hetorthane Yead with ben to fom aU eyh Cynyele
AA mein proud White gem orm tretywicls a
Train procluct - Exphauiy
O45 « Kem th toe ang His Cycle ten tn Saluchon
ken —s £® + Son
* On SON jon Both Corben and nitrogen are
ticker Neh Can clonste Llictren Peu'r but attack
tks Phau thraugh Carbon atom because. O-c hone
Ls mon Mable Man C-N bong
* a4 CN 44 Coualens and oles not qe Sw 229
An Aalution Hen, attacks tharos, Nrtrageh 7D
for C-N bonol and RNC prrluct
frchatiam 4 Muclopwifta fulbstitection -y
LY ~—
SN, Puchalusm SM, DchawsnO Ssubshkebon Nuckoplilic Unimolecular C SM) 4
x gerretly Carcid eur tn palar prohe Salter
Ake water , al(cho ,atehe aciel
Che, GHyOM, CHe Coon)
» Thuy yeathon follows 4irit arcte Lined
Stap To
a" 5 stand ons
eNO ESOS BP
CH Cu CH; Neg
x Siewut and YeVerdebhe Shep
x Trveluy bregting “+f C-By boma for when
therqe Ay obtathed bg salvation af habiole 4p
With prot 4 prot’. helen
Ch Sow Cus Ons
& = d-on poe
7 a\
£ © + OW \
CH Ncw Cy hs Cie Cees
pr
(a) “wo produch earth
aby “¢ onfrguration
Rate Lae for SW, reathon
Rate = K CCH5),C- Br]| Over ay Vea chatty dor SN) Teathon
(7 Gxtader the SYabitity ©} Carhotat®n
aL
Father +e Yate “4 rtachay
ence order ty
(ews )gC-Pr > (CHS), Cw Rr > Copcmby ) CHR Re
(3°) C22) C1)
Rx Melhic, and Bemrglic. habicle pases -nigyy rhachivity
| usr SN, rLachon
93 Dee to SHebikiny cxf Adtylic and Reneylic, Carbicern
formed after rémoval of halogen atom
Oo
Me a — we Sens Cty
i
(oak a BEM Me OR
Skreochuwical A4pee oy SN, Prchanimy
——
x By dg Muchan4m le gu too oli erat ophcay
omer 0 4 and L) din Lapel proportion . tig Wirture
As Kneawn a5 teCerde mixture (Zum ophcat achucty)
# Wan by SNi Mechanism TeCemisatio tate platy
Besson 3 Carbocation 44 phanny tuberrmecliate yet attacked
frm bath Athi 4form mirdure of feo proclady.@® Substitecnan nucleopritic Bimolcukay CSMy) >
* In Huy ykachon ret, cenermting saw Step Conteh
Hoe Yeates (alkyl reticle and Incoming nuclenprvts)
* No fubeyvmidiate, formed
¥ |
' yl
OW + Cone a-CNp tC
7
nh Np Nu
x
#
¢-u +°oH 3
wo]
H
Trangihon Steche
* On FZ Dchanum brea bring C-u bond and Jorg.
GL CoH bond teks poate Atm poicauepeg, forming
UW fable Prwtevatns trantition Stale
Orday co} Peachiity 5
” Mos af ba Rea atkys graup year +he Carbon
atom af C-U bed jncressy
4
Approach of nuchopiiie 24 -Wirolxea
ts
Reaction rede clecresty
Od Cisce > Coe D(C) CHE > (Cr )c-cxi SHreechande oupecy OL SMa Pechanms
* AS ctlace a} nucleophe ee Ay qfourd oppassle
Atle ap Lrauig wuchoprite uence Configuranon
Mf Maleenke 14 snuertecl Cd tot [4 fod)
Tw, 44 Khawn oy snverssion S Contiyurabion
TES wren Compaund Uncltraoy (a, yeachbn fester
i
i
|
|
/ 0
Cana ant Ope
O25 Z SC ihe CUP hakiele)
Nok Order o4 rea chively o4 Lif. —tralvol
RID R& D> Rud RE
C Det fo in cecmus “4 bond olvyocuahm tudralpy)
(17 orclr 4} veaan vce four tome bromebutany,
bg Say y¥2athoy
CI CIh-Cih Cth By < (C5), CH CB
z City Cig cw CHR < (Ch C- Ry
Br
[aa] Orclir “4 rea chiity bg SNi YLathon
Colty Ch Br , Cote CHG HE Br, Coty CHCCHY By, 7 by Olen) Crs)
Gig
ht
larg & Bir > carpe - BrP mC Re DH Br
cuby eng Cy Cb@ Ekiminahion TKachon 9 ( Dehydrohaloynation ‘rAaehion)
* IW prenu op strong, bate C ake kon, No AH)
ere ak lamination ef He adem from fk -Carbar
and halogen tran x Carbon 14 found
of *y
Woe 4 SeeeQ + oH tre
t
1 2
Bo Roe Xm Leauni-g qreup Chatogen)
CH Che + Catey KOH A CH =Cm TRAE Mo
* op tee i peli 4 formation of marc thar
Ont alkene ler to pratense mort than ar 2 iy drogen
Han Major alkene 24 deberminad ator cing td Zaltaug
yak:
Zatisey rule ( Sayjodp rk) 9
ceed set ee
x On olety drohalogmation Teathon the Prefered produc
dy that etking WHCH has gqraster umber a4 abby d
qraups atieched +o deubty buded Corb ote
gf « 8B .
Clg —CH CH Cth okt Kali, Cy -CH= CH Ore
1 1 t A e
HBr # Bet-d-ene ¢ major)
+
CHR Ch — CHE Cr
Bat-I- ane © fuer)sts A ee oy cy
(Major) C miner)
ey ¥ ale Kon + e
(mejor) ( miner)
Nolfe >
* Bubkter Nuclophds ar a3 bate > Cams elimination
a4- (C1), C-0° Chg Ch -08
Bek; Smalt
4 4 . 4
Nackeepity oer Ber oy
23 Bo Muchophihe
+ 4
Eluiminatian Naclophitic Aubsheston
x 12 ky heatct > Sar
20 ali Webi 9 SH] mination
3° atk thalicu 3 SN! 2liminahan
G9 Trtatmes af RG with aquans koe Aros ty ty
formation 4 altos bat prarher 4 ohCoheuie koy
otkin, are mejor producefr InN adieu Kel , Koh clisouare fo Gite Ol }
fon wwlen te ty ign hy abraded In Watir $e prot
bare characty clicreai and Of” avas nuckept,
Re + Kom (on) ———_ Rett Calcohat)
L oS Muto phir I
Nacleophrti,
Adtbihtuhen
¥ 9h aktohate salubian Ken (R0*) Fon 45 pregence
loch 4s Ahronger bale “Han on? Jon ramours pt
Ton and
prooluct
Cotted tlitniinratar . SO elbue 44 major
Reachon with med 7
Ru, RB, RT rea with meted fo form Carbon ~ Mnetel
bendy hm. Such Compaund Khan o4 crgansinetaliic,
Companund
Grd gnayd Prager > C Ate. magician hatick)
CHSC By +My St —> CH Ch oy by
Orrdgnavel Agent
Re oe fe By
« -x 7
Covel = Fowe
4 4
tea ie strong
RO myxas Graghard Aboutd be Prepag Unclirr cuntbydlrceees
Conciihon
ft_ ra'guard Feagenr Ay Hig blag yaathue YLoy Lucy,
any fate a proton (Liter HL from Masia)
to pee shy dino corrbor
ee, “ny
Amy t Hocuton) RAFI,
Hema At is prepared Uncle anbadrany Conolin’en
luura yLach'n 3
ZRr F QNa ti RR + 2NaxX
LCi CH ce FLNa —Mt 5 Cy Ch -CA-CHy
ther A QNaeg
6 CHC
2 ona + rMa OO, 3
Ce
thir CMS CH
Cle cw
Wwurte Pring yLathon >
+ R
ry" ita t Rx bo cy New
Filtig ¥yeachen —
° (7 + 2m Te OW Fann
PipregRaschion a4 Neloarses
Os Arye atic 44 Ley neachise toewarcls Nucteophitie,
Aabsbtahion rLAachon
BSF OD Det PP THOMAne —C-ce bonal tin “Halooment
acquire parhal dauble bord character wWwtn +5 oliffubr
0 break
é
es <— by =o §
@ Dart sp +ybriclied C atom of C-C1 bond th
chaleoriny C-G bond wy pharter Hong oliiffents to break
% ye
(i
y 2
Ss
Shorter bond ¥ f
@D pry canon formed by self donlsanan of ty"
Ay yet dtabilned hy rhonance
@D Elechon xc nuchrepnide raped bg ctictrm yeh
henge Ving
‘er Aubititahon af Ch greup by Ob grap
Noo Naot yt yt On
6 Pe Iman Zoo ahn ONOOTRO pielenes af ehichren Wathdrauiving graup C-No, )
er ortho cind para palin shcneate reachiurty ay |
on.
OW
Macon, Ht. Hf
\ Y |
Tap 4 |
NO)
s on
t
iS No, Nacw, 4 SNe,
Y 369 fe fs
Noy Noy
a on
PMS Ne wwe nm nes
4 Lo
Ne ne,
ELichophitic subthtanan vLachon _,
——
G7 Mihargn Chimie 44 cletn catthabrenoting get te
4s orthe- para direchirg
Pi > Ur As Hheehron Witholreudting 04 af 4y -t graup
hank drereasy chron olunddty anet olacnyode 4'+
x Ber at ay +m group clas ty Lome par Uslleh ‘oltecali
An vhng An Cred, Lu ctron olen grty at Ortho and
Para patiten hence at olireuy Anconing ahretrophit
to 4 bythe and para p xsthonNOL maja)
i] ot Suatprovation J
Z
Son
CMajor)
ag
C Praca) Craps
eutkylahm)
om
thay or)
q “
Sze Ay CPrecut Cray
Bary, AU 4 vl ety todion)
Cre) Cock
C major)
¥ On Luchoprlic Aubshretion CL -raloarany bare thames
44 odwery Jodnd mayor amauur olt AY Lay Stee
yApelaion.