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whom am atem o
haue lessb Inductive}Hectus displocemont o
with
Chavge Oubital)|etooavds nad
tVacont ahcbionuga
o Ro
moe bond lomomt weaR
(Fouma u apamanomt alloet and
1) Ha0 (faumal)4)
FOmaChage)It
Chag
97umd
,
&lectronic
Dusplacamant ect a)
03
axdoy change
Peumare An Sy
b)
63
Inductiue(o-o)
sTempeHONy
Od276376
6 647S2 7S3
Inductomonic
Rosonamc
Pexcongugating
(T-n)
(n) Elhetiomaxiepes t biedailn
+I SeHiJ
-CH2-NH
-ve chaHge)
O
3-2°-1 -
ee) Ccdo g
-c-co
-CH3
(Houp
ElectHon-ullithdnawing
(+I)
wuh espeat to
hum bonded paui of e axe dhifttdtowavds am
asom/ H0up
e withdrauing ioupPI
2
I
CaHbanion
(--
+Z +I
fe-withdyauwinggnops
Qustien
Y-T
R7Pg
3
(9)NH3 R)
F
I
(P) NO2
CH3 oCH3 O 9 PR I
- F
(P) (9) (R)
22
(P) (9) (R)
43
() -I-If-I (9)
-1
(R
K
(S)
RY S797P P9 RS
Resomamce
Robimson yclo.
2Z C-csun'C=c134À 2 CC 1-39A
Kekuulat stuctiue 2 Benzeme
Redonatmg Abuctu 2 Rardonatung tybd
2 Hypcthatital 2 Aeal
han
LUhem popextes ol o compoumd Cam not be enplaum by o imgl 4luuchu
Uauous Jtutwes a
duuon Tmeso 4tuctwes aa kmbon as ason abng/
as
sbuctuxo 8 vteal moleculs us kmoon Hybruüd.
Canmonucal/ contubutmg
RA Point
Resonama s undH amoleculan pHocess
Mae stabls stuctuw contrubute maxe.
ductures art Hypothotcal and vosonatmg hybud au aal
Rebon atumg
Deso calizdtien of T-e u kmown 0 Resonamce.
17 2 Ronana
x(me lbcals
ed
(46er)
(Pm) (defocalued)
17 MResonance)
4P) 4ne-dalocalised)
(Resonance) (Resononcevacan
ed)
(47TeDlocali,
67e-localied)
2 ne(3pn)
4 P)
10
(Rsolu)) (Reso(
(2ne) Reso()12
2
(67Te)
(27nedalocalsed)
P) (3Pm) (Loop) (Lo0p (Pn)
(LooP
Incase oamiln
137
(Sp2hybudusatien
noarlSp2 but
N
Reso(),e,3P RRso ()9me,3PT bemzyne amule
us
6Te
5 PT
Rbo(
(Loopant gne
Rebo ()
(fuwran)
prol) H Loop L0op Loop(6)7Pm
18
He(|9
Raso Resof209
5Pm
Reso
CRvaeand H LS 2s 2p2 A
d-Qtbitals
Ertemded CHOSS
whemow oeloctHOn us um enly whon ow of lectnonuh un
wingldiyerhien multiblo diyedtien
Leas Atable
Mou tab!
Tmpoutoamt Point
4 In onamce,
chamgo
radicab/+ve charg
ofmeons pai-Vechogepa T- Stability
movablo
enery Jelbased
not fiod
Delocalisabien
stahility
edfivede-enoy oloased
Localis
5 Tnthamoleculan phomomomon
bo un Sam plame
un vOso namca must
6 Atoms @
In vwsonanco
arbital which patepato
pu p-oxbital pure /
d-oxbital a patiapatd (unhybrid
bitals
7
wm vwsonamco
nbutal rnowen paiepate
8 Hybrud
ae un natuwu while rosonaing
hypothstical
9 AL QJonatingstuetu
hybu'd is oal wm natuwu
mo conty buhon
Atable Bonabmg sbuuetuu willgiwe
10 M@
Oonating hybud
Dxauwing o Rosonating sbucture
egunv alemt
2 +CH 2
CH2 CH 2 +CH2
(wdho) y(0dho)
lnaetiu
ating
+6CH2
(pana)
RA Point
(Hybid)
By onanca,e dunaihy deoraases
CH2
Hybud
49 CH2 CH2 CH2
OCH2
Achwahn9 J CH2
RA Point
59
NA2 NH2 +
NH2
6 c:0H OOH OH H OH
1)
Pybud)
6 6
30
19 8 2 (1oR
Aduance 201S
T&&
2
90 7R S 100 (6 R-s
Stability R:S
NON
Rulo 1RS. hauing Completn
actet us mow stable
Octet eg:CH-SCH3
inco mpltr
CH2 cH = CH FOumal
Octet
NH2 NH2
(neutnal (ienie)
Rul 3 veon mo &N RS hauing (-ve)en moo locbronogatuwe us
mor tab lo
NH 0 NH NH
(1) 2 06 (3)
-HH -H
-H
m@He Atohl
OH OOH
H
1-5H273 (s)
(1) (2) (u)
(3)
tabl
Rule S itsRule RS hauing maxe Benz ent u mor0
e
(L) (2)
(1 (2)
Resonamce Sect
ElactonDonating Heet (+R/+M) (-R-M)Elactnon w thdyau ing
ham
Pouo o heonus auayom amy tohem low of lectionus towaHds
otbm d gtoup hom that alom Houp to1ll amy group/adm thon that grouP/atbm
(+R)
2)-NH2
+R)
3- CH ei)No2 2) N
-
(+R)
-NH-c- R)
-
RU
(Strongeat
CHa 5)-CH2-CH2 4)BH
3)-CH2
(+R) (NO Uso) (-R) (-R) (+R)(-R)
6) F (4R) 274
(27 (Robin h0od)
6 e (-R) C-OH
(-R)
(+R/-R)
Robun hood 8)-CH3 CH3
wham gwoup |atom shows both (tR)amd (-R (No g)-CHCHs
CH3
1o-NH3
Raso) (No Raso)
(No Raso)
-a,BH -T S-OR
qoHOups
aAet wll
uhich can show
Shouw
nt e
+R as well as -R
N=NH ecton
(-1) nubialsystem
egi--x
(halog en) ,
(-1) (-1)
AMomaticity,
Compounds which PHoducos 0imgnatie Rumg Cuttamt un pas emco o Magnabic
old ao known as AMomatic Compounds
that Conpound
that Gyclic Rebonane?
known as
(Rung uvwnt)
QuasiaNomatie 4n)
Te (4n+2)
No Te 23In),2.3 ,)2
10,19-re4,
Te 2,6,
6e
2 Na) 3? A) 6Te
(AMomatic)
(NA) |6 (NA)
1 4me
(NA) 8
27Te
9
2Te
109
6Te
T @
67Te
12
Te
(8R)
3 47Te 144
67Te
15
A2/Te
QuasiaHomate
16 174 6ne
4Te @
Thikaund
0> 2Te-(NA a6me
197 @)6ne- 20 21
6ne-
o
67ne
229 23 2
0Te 6ne
6Te
25 A) 21
67Te
mor
Nocalised1
28 29 30
9ne
147e 8ne
(Annulone) Cycloocta
UTethaene NA) Ot af pland
mer-plana
MA)0ut of plana
(mo-planul)
uth lezubility
Tn a ung,appl Huekle's Rul
singli
* Tn ca e-bond Co bond pesent than braok like --8fa
C=C,biak uch po so that allUumgs beromo Atomabie. h
Tn cass used vungs soloctdangest Joop &apply hueklos ule 8 Varget
Toluon
5Pm (Entendad)
RingC
2RS
0 3RS O 6ne-(Delocalsed)
27e-(Loc alisec)
20H
(CrOs) Phonol- 5 RS
Spm
6Te(nelocalued) Rivg(v)'
2ne(Localsed)
Phemonido-2
2NH2
Ring (5-RS) Pa,1 SRs
8ne- (Delocalisecl)
one(Localis
ed)
Ringl)TO
4ne (Delocalis
ed) Ppidune 6 P 27e-(Localue
6ne-(Delocaliyed)
4 PTs Oping 2 RS
5Pm
Py ole
Te-(Delocalused) Rin gl)
6n e-(oelocaliy
5 RS
ed)
H
4Te-(Localscd)
Hypecorugation(1932)
CH3
CH2CHs
(o]
Case I CaRbacaten
inding
l2)
H
CH3
-H73 2
CHa CH3
Hypeuconiugatuen
)
um Cobocatiem
7
Co&e AIkenelAlkyne
CH2 CH3 2)
9 6) 7
HC
CH3 8) 9
CH3 (-C3
-H:5 5) S
HpenceTyugatien un dokene
H H
HC-CH CH2 HC=CH-CH2 HOC =CH-CH2 H-=CH
H H H H
6H C CH CH2
6 ybrid)
fuind
fuincd Tota HS nuoluing C-H Bond un FolloingCompownd
H
10 9-
66
Aav 20 SH -
4H Bdh
H H Ben 2ylue
uperc.niuganen
HD-H P-H I1
um
. Bemzene
HDPca
Calbeo
Ous de Hypucony ugalien, e donsity 9 Hype +2
unbuasesat oP pasitien. o -Totdl 1 pen
Hupexconugotién loet
Peum anant et 8) tma
operdtas at oP pasihens Benzan
2)Hy pothobcal Contapt (HS) 9) -H,maxu (+tH) eet
notin
3)HC slctunvolue C-H6e 10)H)fut shoon
by -ccg(XJe€)
11)C-H CD C-7
1)
4)o eMOmti oly poubcipated un HC O0
un HC ffeeds e 4frong
5) HC let u uek cd than esonunce bcaus
bond a whulo un aboname
panticipalod 7 bond e a partiupotnd
Becausa C-H 'easy
Bond
R 7H7I do Be ak.
16-NO02
15)-OR
n)-NO
-I
I
-B--1/-I
+R/tR/tR
-I
T
tR
+R
-R
-R
R
+R
+R8R
18-NMe3
20-CN
22)CH2
9-CH3
21)-BH2
23)
I +L
(Somuhme
+I
t1)
R
R R
24-PMe3 25)-CO0H -R R
26)CHO 27)-0 -I+I R +R)
20)-COC 29)-CONH2 I -I R R
80-CH CH2 31)
-I R tR
CyckopHopame
ut us
Dut to high ongl tnoun
rog 60°
mast uMstable
O 2u.5 245
Bonds m
L
Cyclopape
sugma
hahawe
bonds
ike -bonds.
o yclopopam
ENGtyclopuopar H H
Du te Hiah 7.sun
C-H bond,ut bicom
60
H-C-H sT,
ENT
.t prDUides
Hesonamel.
shown by
vey h h
yclopopamo
,
amcing
(sigma
Resonmance
Mout stablising
Phanoman 9.
L
2 D
<
<D D
37
+
Ph- CH2
3
Dancing
Brudt'sRule
H
AccaNdumg
o hs ul ung8, thon
plamanty (sp2)
Can't pasu bl
be at
budg canbon o bHidgo atem.
H
o1lR21o
Roal)
4 5)
9)
Total HSS 3 R:S ()
CH Bond
involving
(notpassiblo
tHeat o Combustiem
RA
HoC
Point - HOC poH CH2
mo caubons stabilit
Atabilitu (R)Pra)
PR74)
2)
( (9) (R) (P)
(9P)
(9P9)
4)
Colculabiem op HOH
1) #H dh gwen data ,yund dOBon anco eneHgy
H2
AH30-o KCal/mol
i) 22H2 H -50-0Kcal/mol
i
,
2) und
2H
tho
2usonanea
Ha
J
(HA)enpeehd =
btab!isatien
OH542R-6-3
60
emwgy
AHH-28.6Kcal/mol
H4 y9.8Kcal/mol
Kcal/mol)
Col/mol
Kcal/mol
Benzene
R8 -28-6)x3t49
RE=-858+49 8
RE-36 kcal/mol
KCal/mol
1 2)
hesonamc onu
UU
eleased/emgy d eunce b/o stoblRS
Cnovgy
amd hy bud w lm owñ as Rzs onanco stablusing
RA Point
REX lactiv
eness of Rusonamc
<[oya)
2) 0m) O N
6xtemtemt RosonamC
) (e
Khachu
(P)
PR29
(0)
)
(R)
NH2 7
(Becau
OH
Nil
(
do mor
e eechue usononct
b
denahng
(Duut a 8A)A
A&N(0N> 3) outite
RS)
cq ,(Peya"P
aso um Benzema)
(Ring notAro ma
CHa 9 CH3 PhO Y8)
36qu (SRSon26qui Arom
Rs atie
9) They a somnd
o Tntemg dliate
Stabiliy
(+)&DG 88
i0onicing
-)Ew +H+IJ
()+R,-R,
Tntic
R
Reo) 0ipde
Momunt>9P
NO2
N02
3 NO2
oo bend Lemgth
(C-N) U
(P70)
qHoup ize
AcidicStength Peuod &N.
RA Point
Acudic stungth o Ka L
PKa
HA H+A (CorugateBao)
1)SLR
i)H-Bondimg
Ka [H1[A KotCAJ
inCB oC8
stability
iü)Rabonanc CHA
H-bondung ot CB
iv)peconugaten ofAHomatuc pKa=- dog Ka
inAcid o EwG+R,+I
)
v)H-Bondug
vi)Tnducide
ae. d Qdtho Subhstitutod 8emzoic acids a
tR,+H+I EDO most acdic among us&mos (M,P)
1) HF HO HB
F C T57R9
2) CHy NH3 Ha0 HF OH DH QH OH
SR79P)
N02
3) H O
OH
H2S
HS
H (R79P) E) RNO2
(PRY97
(-T)
(PoM)
OH OH
OH
OH
H20 8) COoH Cooh
o
Ph-OH
OH o
CH CH3
5) CH3Co0H
2 eq
SOgH H20
-R)NO7
(Leq-
CRNO2
(2eg.)
CH3
2
e9) e)
(ey )
(9P>RYS) (g A>P7S)
(Gy R P)
oCH3 (P9) ÇOOH CoOH
(PR9)
COoH
COOH COOH fooH
(P9R)
a)
Lo
(tH)
oro
12)OH
COÓH
H-bonding
HOOC (P4)
(Maleic acid) (Funvue acid)
(P>9R)S)
CoO CoOH ng
-CoOH
H-bonding
18) HCOoH Ph CoOH
AH-bondi Reso)
COOH Co0H (P9)
(Reso) (P>O) (x Reso)
NaOH
QH
(Ogamic Solvent)
3.0
Soubilihy8 Alkame< Alkene R-NH2 <R-8CH <H20
H 6-35 QH pH 15.7
<Ph-0H
9-95-10
NO2H2cog< O< NOz 2Rc00 H<
4
KS0gH
NO2
<HO OH ZInagamie oud
NO2
POM
Squaxie
acidHo o FoH (HCR H&, HNO3, H250y-) Porol
tho/Meta
Basic Abiemg th od
(9)
U
edonatng tendomy
B H H
to am H
K CH8) pkbgb
CHJCBJ
R.A.Point
Qytho ubaituhd Bemzem
Bauic tmgth kb
Animp au Joast Badic among
edenaity (localwed
&DO (+R +H +T)
&
8d(-R,-1)
EwH
Soluatisn eet(SIP)
NH2 CH2NHh
2 QH 7 O
COO
p la PkaPka)
2
9 NH2 NHB wn aquous SoluhOn
2
23 2
3
Na
NH
COOH
CooH
)
2
1oKH
HOOC
CO0
COoH
3
12
UH2
C00H
)NH
COO
COo
HOoC COOH
1 CooD ONH
COD
12
Coo-2 Co0w
NH2
1200 NH2
COo
et*tt*
Soluathen ect
Bauie bumg th of Amuna in Dater CH3-NH-CH3 CH3- N-CH3
CH3-NH2
-
cH3
H.
-o. Pg7R o 3°22°
H
0-H
CHa-N HOH H20 172*73° Solvahion hhoc Hbond
H H Net 412°>
1°3° Me
H
273°1° &+
ONth Subatiuted of Anilime 0 Ost Badicameng u womas (PlM).
NH3
o
NH2
H+.
O
Backo aHd
duo to JoastSo lvaton
NH2
N (Rao) R 2
H H (RY P7g)
TautomeUm
desmolnopy
044cdN aten a migation am atom bond u kmoun as lauutomusn
30 OH 1)Diad -ohan migalion tokas plars
HaC--cH HsC-C CH2 bahoean boo aty
STPAototuoPH) H-CEN NA
(Catio
notoPH)) tokas
B-whan migyotien place
2)Tuad
OH betipean tHoD Cdormy
OH/H20 30 PH
HaCC CH2-C-CH3
(enol)
8)Spac g-whan miguatientakos placa
HoEI) Ho (O1 booewn mau than thus atom.
50 OH
HC-C-CHs CH2-CHa
H
nol Tautomrism
*Keto
Carbamon a emolade ion obtained
Ezist us dynamie equillbrium (awke)
RA TUGHAD
hemove the H ,sothat corjugote base willshow Kesononce wlth elacdonegalive
afom (0,N,S-)
9
(4)
T D
(4) 6)
T P
( (1| ) (7)(88 T
(3) H 3)
12)
3)
)H--H (X) ( (x)(o) 13)X
(6) (5)
O (3 T2)
3)H-H (3)(3) 13)10N
2H ()(5) (99 (a)
(6) (S) 9)
(5
(e) (4)
4 (x) (O)
lo) (2)
(x)
(x) (o) 15) FO ((o)
H
(3)
(4)
Deubuium Enchamge
OD
OD/00
H3C-C-CH3
long tim DC =C02
1
SHim
HaC--CH CH3--CH0 C03--C03
3
Yaxm (-ve) & duauo RS, (3)
a
pMouido 'D'
at which (-ve)
pasent duum
Rabonam
3) (3) ( (H)
(1H-7D) (13H-160)
of kato
Stability &mol
0 OH
enol
Aldthyde Reto
(1120k3/mol)
(I1
60 K3/mol)
Kuo enol
OH
7.enolX aHomatuC emd
( (
99-97
1,2-dicorbony!(yclic)
(1007.
Kato)
Cl007.
enol)
1,3-di covwbonu
0
OH O
(767)