HALOAIKAN6 8HLOARENEs (01)

(u)) 9Nu@) 1
t
(BimolegularNucloophaliebubabtulion

CH3 CH3 2Nucdaophlieily

TT

l
OH
Reactien
C o 6 3)Ateuie Hindaram
A 4) Tpdaney TT
D HOD
w T
inwesion)
x CH3 CH3
Mechamum-
+oH Cww +X
HSX HO D
D CH3
x Hghly Unaab
HO
*Sp2 hybuidsed
D 10 Valncoe
H
30-4e0 bond.

SN s a Aungl tep aetion.

No corboc cionda ho vuavamemurb
Anion likocharacdey un S
*T:S s 3C-ye Bond

)A
sp hybidued T-s.
E CO stahlze the 7-S
o
oSN o Hato o R Uno
Waldom Inuesion A mist
Bond Tnuexsion takas plact h
Kimctic Tsotopiceet
(x)
* PE-dagram

elamandal ot oba0Ued, (cac)m u

K
 8 HRLOARENES(02)
A

Unimoleeuday
HALONUKANES

NuclaphulieAubatitubiem (SN)) A CH3

CH3 CH3
Raachen
A C PPs (Ha0) C Ph

PH x Dalacbuo ConsdauPh
OH

182) (Inweuien
Polaxity (Retonti n)
Machamisnm- CH3 CH3
Dgul
HH H
He0 0-H
Ph
C
H0 H
H
Sp2
*plama Soluation Eng
*Coubocatuon

CH3
CH3 CH3

+Hao C n ph
Ph
OH HO
Ph &t
*Emamtiomars
Two stp vuactorn Racomic Miztww
Casbo catien as ntemodiato
emont passibl. X
Riawamg
Raemid Miztww Obtainsduoh VUN o Au tg
*No Kumatie Isohpic Eect
* Unimoleculay Reachion
Rato laud
Ract o Rx
HKLR-XJ Psudo
= k/R-xJ[PPs),

Polavihy o Soluent LnS LOO7.

I do edcher
Racsmie mixtwo not obtunod
Stability Caubocation Ph
E DO
Bond Dusoiatien
Me C
t Me E Me

Leauing Cvoup emdom cy

Tntimato Ton pau)So)uentSepavalod
pai
Ton paiy on pai)
Both unuewion Red enien 0btainod
TighTon pain)
Guaph of Rxn8- Tn Snd, maw
Inwenw n lessrotemy On
.
,
*
(SelventSepenabd) (Cempleto)
(Tnhimat)
PE RD

R-x 271 987

P.0-R. Net TnueI®n = 49 +2 s17.1, 497 R
 aetouso S amd S)t

1)
Atuetw o Jubatato
)SN Ranctien 8 (dess dtndovad)
N
Ph
ph CH2C
OPh H
H
1M0

b CHgC Nu- H H

)
u Me
AMe
e

Me
).C
d)
Nu
Me
--u
Me
R09

OMe

Me-0-CH2C AA

Rate o Raactien
ab c<ecd
) SN Ronotien

3- 1-3,Me-0-CH2-X
X,2-X,

R-oR dab
e
2)Natu oLiauingtouP 3 Nabow oluemts

qood Moderato 1)SN Rano PAS

PooT

-C -F i) Sya Raac" PPS

N2 OH
oulb
) Natueeo Nueloophile
-I -0R )SN2 Ras Yood Nu@
ONS -0Bs SNL Reaen weak Nu
-oTF -0Ts SR2 S) Buanchimg-
OMS i)Su2 Reocben 3 2eIBManchimg
i)
Sp Roae Mavo Bamoh
maa dusocraten

SN2 SN
ED/6w &wb ED A
a Tendam a Hgh Lo
Solvent PAS PPS
tuincyamee Los
High
CNut) qvod Weak
Nucdeophiliaity Hgh
B am chung Less MoHO
 o

) Reoctiem with Ag

-F R-F
1OMF
pplicatien

Swavctz Raaotien
SN)

I
Halogen Exchange
*2, Sbf3Cof2

KEN R-CN
funcional
AgcN:R-NCuomu Ambidertata
Nuelesphile o
oill
KANO2 R-ONO
funchional
AgNO2 R-NO2 isomu

Dry Aga0 R
o *2CH2 CA2
H
Pow doi
CH2 =CH2

Mauh Hq20 R-OH 2 Powclo6 Ag

CHC
CH aCH

Ag Pouoder R-R

I NinXSN

)
heactien8
2fumk elstoin No
R-X+Na Renelion

R-X Na T Hcepra RINux,aj *Inuesion

yO
o
(Covadet Maxa)
* Jajan Rulo-NaI a)6
O
ationpet(niax)
O

* ving avofoum

aR-a
3SN
20 SN[SN Rso) H, pEls RCA

SN2 Nu) PCRs R-

SOCP2
SN(d good, PPS) OCE R-CR
lBpidin yR-
#(Reactien,
with H-XK

Geacton 8 R-OH+Hx R-X + Ha0

oohot
Machamum 1) R-OH +H-X (ROH2)
2)
RtoH 2 ids
Hds R + He0 (2,3
3) R x R-X
* Caubocalion Tntewmacl'at di
ReanHamgemomt Pasiblason
Su2 s -x 8SA s 20-X3 3-x
O
*Rato o Renation a ewmt
cdlilt R-oH
8-oH
2-0H 10H CH-o)
SN2
*Rado o Renotien farHX

(HIY HB HC HB

*Dexemt Conditiens u HX 9

HT mo conditien(Na1/HsPo)
HA Constant heat Na&/ H3foy ¥ Vab/2 ) aA a
3)HCO H0, A (70boak HC), H0A(A4c3 Sbca,Feclg,ZnCa) dy HCe
(LUCAS TEST)

Poc8 R-OH H0 tZn CR2) R-C qHooUe s PHocess

Solubloio lucas Inboluubl0 um
Reagent
Lucas Lucs
(whibo tuebiduhy) Atab.lih
p
cdopemd Kdo hai
3-0H mmd eb (So)
20 -0 S-7minutos (S)
b
-0H No d(n)
tweielihy Sp?)
at Room
Temnp exatwrp
tReaction with Pus

Reachen& R-OH + PCI3 R-C2+ Ha03

Mechanusm1) R-oH +PCO3 R-o +3C
H
w2
RGo-e
o P-0R +3ue 3R-OR+ Ha PO3

H
Druving foicwl b aumatien P-o Bonol

* SN aootien Occws
Inueion Occus
we Cam allso usMd Rad P+ CW2

6 timos SN Henetien takas plac.

Me
19
PR3 2)
HOH
OH

3) PR3

F(Roactienwith PIs

Reaction 8- R-OH + PRs R +H +PUs

Machanism-1) R-OH Py R--P H

2RL- H
PU
Co
R-l+
C9
R +H + PoC

R-OH Ah ows SN2 machamusm

achen s amauen aP-0
*Dquingfaxci ot
takas attack
* Incas etheH fut attack s SN2 so inueem plac and seeond

SN NHP SwSo etenien takas plac

(axzon PHoces)

Raachen- R-OH + Sou2 R-0+HC T tS021

Mechamism
)R-OH+ R-O-S R-0+S,.+HCAT
C

2)R-0-St R- +S02

BB ,BF
-ö 4 MCTS Coneted Meehamsm
* SN inteunalnuclhophil
Ce Bs * Redention

wih Pypidima)

R-OH stce R-0-o+Ha Ca

Papidim

C CoSR- + So,+ CR * SN mechaniam.

*Pepuiduni ay Net3 can bo used

AAK
Inu ewnoh
akas place

(ALRylie lcohel)

CH2 CH CH2-OH
SD2.

8 A So SO2
XH MCTS
+SO2

S X6MCTS
soC2
SA
oM
BF
 Aumma Me
+ SOCl2
H-OH

chimne AQeye -0H

Pyuy

Me
Me -CH CHCH2 CR
Me *SN H*SN2Tnu
H Ratemtion exi@n SN
D
D

CA
OH HC SN
ZnC2N

PCRs
*SN
C
PRS KSN
rC
SOd
*SN
SoCa 1 *S2
Pgydieoufk
#Cloawogn Eher)

By HX

Jugaad R-0R R-CH NH 0H

R-CH R-0-R'
Ho JHgo OR' HX
R-OH+R-OHR-CHH +NH3 T R-OH + R'x

R-CHO + R'OH
R-CHO R-X +R'oOH
 Meehanim
Mlcehanium8- H- R--R +)N, Maun&
Chock
Chock fo
far
R-0-R'
H/H0
R--R (H20)PPS to boak

Caat
1-OH
TC t31 (SN

o{3°)H2o (19
Stabl 1-OH 3-OH (SN4)
Cahen
not always

Ca 2
1-oH+ f-1
(sN
-0-
1-0H+1°-OH (SN)

1-020
H
Heo
I-T +2°-0H(Su) lo
SN SZ PRs?
OH t2-0(sSn)
Ha0 Sw Sw

I
IPPG)

Cene Hx/Colcl HX/ HX (1en,)Saums.

HI,A Hot HXHI(enCos) Same

Anhydyow HX alvay) hous SN 2

1 20
HL I*7OH
Ho oH OH

H
Ha0
T OH Ph-0k
H1 PhOH

H3oPhoH
OH

OH+ OH
6) Ph-0-Ph No Reaa"
H CH3 T+ CH3CH20H
9) 2) CH3-0-CH3 HLCHOH +CHaI .
H0 CHs0H +CH3 CH,OH
HCCH30 H
 o
Avomate
(Bimoleculay Nucleophllic Subahiltien)
NQOH, 623 K,300atm
Reactien
2) HO

Mechanm C oH C OH OH
C
OH
RDS

2 OH7
-C
OH
o9Na Caubomn
m complex
HO Lo EW at oP w
a
inctoaso ab

*Caxbanien Intewmediata

foHmatien of m-complax us RDS

*Racto acien ctm
stahility
0- oS
-Complex (anien)
stability 8w at @utho Poxa
pasitieri
EDo o DaavingOup

-1
Ewy at 0/P poaitionwl
hact odauing roup ww
F
(AH- AH-0
Unta

7
as Hato o oaction SA
una asthe ato
A-BM 7 A-I
S
 ation Rancion)
(Bimolecuda Elimin

Roactien
Ha H AD

Hak BB
Machanism-a)
BFBB

Hb bb bb
bf

XAg KoH Ale KOH NaOH/ Ha0 NoOHR-0H

Nu Nu6

Modaxat Bas sbieng Ba #Poor Ba

RO B,oH,
NH2
0Na NR3, SR2

KOH/EOH Alc KOH 080AB "Conwded

BO Machanwm

Kaavhg baou

x
Casa 1-Moderato Baso
us vey 900d
a ng)tp)mohen deaving roup

tala willdok dikee4

lo Ttanudion

catien ika
C CS+
C

pHoduc us caeiclodl al
butabillh
Ma @
d
AOkama
 69
gNp tohen earing goup as modex at
Maj@H

-
PHocluei
B

-c c x
alkeno lke 7-S

(83
daciclod by l

Ro
2) Ro

Cpg whon auing group w

vey poo0T.
pMOduet wl br
May@x
dacicdid day slabili

Ro

Case 2 sbiong Ba A
AO
o NaNH2, NEt3,DBN, LDA SLA
L01o
a)dp g- tohern
eng base w taken

8
Ece iko

x 658-

tBuOO

stbHong stabiluhy
Baaa
Base
100d (ALkame
4tability
Modonate Mo dayato

(Base
Atability
XPo@
 H20
OH

H20,A

etoNa,
9

uONa,A

NaT,
2Et0Na,A (e)
Ce
AAFf

(8) HBuonM, AM
D Wa,
2 HBuONa,A

#(Hotmam &xhaustwe Mathyl atien Emimatisn -)

Machamus m
CHt CHa pCHa
CNH2 NH o Me
Me VMe Me3/

NMe3
TO04 Me3
+N Me3

Broaking R-x Bond by (NH3) ammonia mo lecules us own as Hmono au

R-X
R-X NH3
R-NH2 R-XR,NH-
(2)
R3N X(R,N®)x©
(1) (3)
Xfov 1 amune, exces af ammonua us takan