Physical Chemistry

Watch this:
HDRe GAKGONS| Kolbe's
elcd. Jc Aaids
illman NaoH
Rx +(R',uli
CDREY HOuSE YNTHESIS

Rx RR
RR
AUKANE 5 Cad

N/Pa/Pt
+ M2
NatDE. Wur6

AIR NABHy2/3 I*x*

Hyc bra+bPratolyat
SnH12s
R MyatPhg
thV

]
Q9: koH N2

hi
HXC" muth
ALKYL

el
HALIDES PO2/Pa5 /Sou
ALCOHOLS
Lenc. S y4

ferr.P +I2 H at 4/3K

AlC:
frs HerIRo»R
HXa ct
OR
D (443K) Ether)
R
OMD go, ITHf
ar OR li) Na®Hy
SH Mo
kOH
ploot 2
T
t Ba-0
Gulk bo0 >AKENESk
[II

n_add" NBS So,

0 Tollen's
LOs2 whitep aliadd
me-
c= f
Rud B2 Bayey' egav kviole
4
OvovDn
LoleuY ) Per-aa
oR
ind 8IR
ru

(Anf) Jmp8A
Na

Ri
Na - Na
tinNako+0
Alc Acelone
ainlin)8
Ti

NoNiH2 NoN2 (awti) Ayahanfr

Tetmina olbyna
05
A L

(viote)
DR

gam)
--
 Page No.

PHENOLS Date

EPREP
7 Y Me 1
683 71 Na0H
3oha HhSo enC HNO

H
So NO2 O1me
ummone
toouad
SnH
HO
DS1NaNo,t (mistien)
H wo H0 OH 0
OH OH

(TReacfens BY uwhite pp)

koH CO
Coo
CoOH
kolb c6
Schrvdt CO OH PCTIe Acid
Of1
kon (Baeg)

Keinne lienmann
Penai
6laum
eno
quineme
:CCe
C OH OH
OH

Sreom NO2
disflafion)
CenC

HNO
 OH
(O-CooH
Page No.
Date

L o t )
C h - - o H
0-CH

HC00
DK
-Ch,
-CoEH

R
Pspimin
OH

CH CH OH
Ht
AG0-

pil winleigpe
PhOH
O
OH
+0,
C-010Salel
(ankdephe (saticqbe acid
Pheuol

6te thod atTen

OH

N=0
HNO2
NU
CH-C-0

O So DH
HO -So

NO uNO

NO
NO
 Page No.

Date

In kolbes kn
ONaT O
T1Y0'c
G80th paa
CwPT
ONa OH

P 4-6 an
OK OH
k,
Co

OH NH,

Zn
OH
cluor

Rieme Ticman on Pyele

HO

C CHO
(aye)
 Page No.
Date

TESTS
0 wolet Celour w lral ted
Erete Lonen
LNiheso (Libes mann)
OH
OH
NoNo
HCe
N
ONAO Indephenol

NaO
CkoHT

d u e 1 o e t e o b l

Azodye Teot

OH

HOON-N O
Paoahydrot Azo enzene

B , aq) s t e p
OH

67
Ti
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 POC
nmayy
trUAttFARUE- a (oH
CalDtHh0 G(Ho)
Mitkindd
C
Ba(o)a> baC H o BaBa CHo)
nilkiness

SAy
H Cuso,5 H,o
Bue

ANa ÚN_ Fes F,Fe ( J hisianblue

N
NaSN reS& fe (SN), bloodl red

t2
+2
NetFeet
NaFe C), NoS Vinst
Na, S
Pb(OH,Coo0h PbS)
)black ppt
To emoue S/CN aH,S)HCN
HND, (Pn N,)
x Na x Ba lute ioluble
aBr Pols yeleud PaxialPelbblk_
yellou Tnieleb
fhmma phho nelajbcld

P Ng2 Na, Po N,P No

P TTBtgbeaale
PP Volyhedale
OR
yelew f
NHRy 12 MoO
VANTVANTI TATIUE
Cu D lo, + Ho

koM (all2 J aberb wt giuen

No2/-N=N-/ 3

Duma M TELDAH
a) uo N21 a) nso NH2NH4 J A
b) N ka Vel guen
6 NH3
c) tfratien with 504 V
3X Caiu NO C o + Ho t

given
No
() HNO
6all Ba SOy
wt giun V
Louiuo Tube)
MNO HPo
Armm
molybdake
Ticase
Mg NHy PO 2 P0q
H ,Po2 Mo0
Giuen w.

6
COTp
+2
Co kei eR Ra
w iven
St0+1,05 I,+5O
 Page No.

Date:

ETRERS
Prep 0wiliamson nth RoT+ Rx + R-0-R'
Cenc
R-OH R-0-R (R-OH acts ao Eand Nu
H E) Alkene
Alkoxy eY. Dem Ha CoAC,oH R-OH
Na BH NaOH
R-oH H-0H 0-C-H,wibe
ata ched

Ph-0+ROS-DR_ Ph-0-R+o-5-oR
oH

Boae)

Eporuy cc D, A
Xpfi
mepbA
aofev =c

+ebG (H Re Soath waala

O aala hai)

eunGven her 12- eon- 4

 Page No.

Date

AidAad leauage
a) Demo mese kC_pe S1 S
b Deepe S V SNS2 V

Me
CH
ApHE Me
Anly HE R-OH+T-R
SN -

O-0-
O-0-CH=CH r DH+0= CH-H

yclic Ether ring peninq

Aad Booe
|'o'H eke Laban se bond Nu wahan qttack maaiega
fodeno aban C dable ahan d+T auy S.H

Me-C C H
RMgX
me H
me Me- H
me OH Me

O2
Oxd R-OR R-0 - R- 0 -OH
(eny tat R which hag Stable
+2
Remeue fe" cene H,So faee Tadicol en i a t leaot 1 H)
KT +Stârch (8ue lelour)
O
Claisen Rea H2- CH=H
palat ke legta hai) -CH2-(H = H2 OH
-MR
baa
palas CH-H =H,
 elasSMAte
Date
Page

GOC
RCR H-RH D
NRa -SA,> -NH NO So,R Ar
fewG)
(ewg)-C00H Fru>BrI -o-Ph oh -OR -2-R>
SH SR> -o CECR> -h - H=CR,

Kesonante. e C c - d -
mubmen c a fype efonane Stability ) no. bera
net a) enm eNTalem
-ve
hybrid alu shuckne aut cu
8) Chogecl/uncha 1¢e
XXy Cem mbulien
e N atom a ulta naui hola !
3 dliuiont 6cutnplile e
NH3 H0 4,8ruderphile

H0 etC XXX ETno N XXX

Nu XXK atack C#C- (vepef maaeg
but com attack -C >o

Hype Trjuqofion -TT ouTap

-C-H
oR
-H2 2eo HC Kor CT
H,C
sut of pane
n0 pertovgafron Y%.
 CH= H inyl clASSMAte

phonyl Ct CH Date
Page
benzylic

5. axbe alion (AFA Carbenium)

Ca vhonium
Sfabil ty Ahrmlieil CH
Resonang
1) HapeY wnjugalm
I Tnductue
pital ao
a) CH3 =H- H
CHg H
6-c-F CBr

->F/u/8rI agarkinC 6bann gya C

R

C)

Dantirg
esonnce

RasYangemenl C ReZyada abl Oanane Re

(Stability muo ingeaewhile ye
duifting)
ing Npancl )
 alassmAte
Date
Page

6FreeAadilal
CH2
Stabiy O

7Carbanon Sp
Stabiuty a
eCH eme
Me me

Caroene : CH
215Ttt-

Sp10
mulrplia tSinglet Triple

H
gentrolOfabiuly
( paihing energy in sing)
futk
ending CF2
V
ca, >:CB22
V V
CT2Singét
Cf2 Ca C62 :CT2 mplut

obenZyne (dthqdrobenzene)
Arcnmalie in nalúre

Sp-SpDuerap
 alASSMAte
Date
age.

atp alomrs
Aromaliaty Cyclc + Cergugaled 7 fonar
Hutkh
Hutkh rule
Ly (tnt2) TT e3. Promauc.
4n Te 5 anf Fhpalic
H
H
NH2
fypical
N

NN-H H-NAN-H

3-Amulene nem-Qwmalic
1o-Anulene (nonplonwr)
non Armalre
plana
nen-planay Cyclo9CIofefen Cy clooctatelrene
danien
14-Armnubne npn- 4 p l i c BuT dtholro JArulert
0pmalic
nennen-plarar
H
H
P

sfaf ek T bonel løun hega

Cey ugalien mu'n)
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 Date

CoOH
NO IDS Page No.

NH Serin - H2OOH

Aroine mreenive CH
0 Guind - H
Sif aa yrosine OH

Alanine
petlo, kat ae qulabjamun
P G
ysfen - CH,-SH

-C
Ag enfna zanori hai 5Methionine
Valin Aginine a .

yine
-CC 10 nen tao.
Avginine NH

12 ty H-NH- NH,
Prolinc NH
COOH
C
Pheny Alanine
Hisfdine NH,=-H=00H-
Tro sin
CH
Aspare Add CooH NH

Gutamic Aad 1 , 1, ooH

ASpaYagine CHl -N2

Typophan COoH

NH
Gufamina H

NHa
 ranjan_tatsam

NAMED REACTIONS & REAGENTS IN ORGANIC CHEMISTRY

]
S.
No Named Reaction Reagent Use Remark

hi
No rkn on deactivated ring or with Ph-NH2, NHR, NR2
1. Friedel Craft Alkylation RX + AlCl3 Alkyl group on benzene C+ rearrangement
Order - RF > RCl > RBr > RI

CO + HCl for -CHO

2. Friedel Craft Acylation RCOCl + AlCl3 Acyl group on benzene
No rearrangements

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3. Clemmenson Reduction Zn-Hg conc HCl C=O to CH2 Can reduce NO2

4. Wolff Kishner Reduction NH2NH2 in KOH C=O to CH2 Cannot reduce NO2

D
(i) SH-CH2CH2-SH in BF3
5. Mozingo Reaction (ii) H2 Raney Ni
C=O to CH2 Useful when comp is both acid and base sensitive

6. Corey House Synthesis Gillman Reagent - R2CuLi R2CuLi + R'X -----> RR'

To prepare CH2=CHMgX or Ph-MgCl solvent must be

7. Grignard RMgX As base or Nu

T
THF not DE

8. Birch reduction Na in Liq NH3 Trans addition of H2 across alkyne

9. H2 + Lindlar's Catalyst Lindlar - {Pd/BaSO4 + Quinoline} Syn addition of H2 across alkyne

10.
H2 + P2 Catalyst

11. Wurtz Reaction

P2 Cat - Ni2B

Na in DE
[II Syn addition of H2 across alkyne

RX to R-R
CH3CH2X gives mixt of CH2=CH2 + CH3CH3 +
CH3CH2CH2CH3

12. Fittig Reaction Na in DE PhX to Ph-Ph

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13. Wurtz Fitting Reaction Na in DE RX + Ph-X -----> R-Ph

CH3CH2X gives mixt of CH2=CH2 + CH3CH3 +

14. Kolbe's Electrolysis RCOONa + H2O RCOONa gives R-R + CO2 + H2
CH3CH2CH2CH3

15. Bayer's Reagent Cold Alk KMnO4 Syn addition of OH across C=C Pink/ Purple colour gets decolourised
Ti

16. FinkelStein Reaction NaI + Acetone R-Cl/Br --------> R-I NaBr/Cl are insoluble in acetone

17. Swartz Rkn AgF/ SbF3/ CoF2/ Hg2F2 RX --------> R-F Aaj Sab ko hugg (Ag Sb Co Hg)
 ranjan_tatsam

18. Darzen Procedure SOCl2 in pyridine ROH to RCl without rearrangement Inversion of configuration

19. Reimer Tieman Reaction NaOH + CHCl3 Phenol to Salicadehyde dichloro carbene is E+

]
20. Kolbe Schmidt Reaction NaOH +CO2 Phenol to Salicylicacid

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21. Williamson Synthesis of Ethers RL + RONa Ethers prep Elimination may take place

22. Rosenmund Reduction H2 + Lindlar's Catalyst RCOCl to RCHO

A bulkyl intermidate is formed as ppt preventing further

23. Etard's Reaction

el
CrO2Cl2 Toulene to Ph-CHO
[O]

Not applicable to phenol (and their etheres);

24. Gatterman Koch Ald Synthesis CO + HCl + AlCl3 + CuCl Benzene to Benzaldehyde
Deactivated rings; Benzene with NH2/ NHR/ NR2

25. Gatterman Aldehyde Reaction HCN + HCl + AlCl3 Benzene to Benzaldehyde

D
Applicable to phenol (and their etheres); Not applicable
Deactivated rings; Benzene with NH2/ NHR/ NR2
26. Gatterman Formylation Reaction Zn(CN)2 + HCl Benzene to Benzaldehyde

27. Sommelet reaction (ADV+) (CH2)6N4 Ph-CH2Cl ----------- > Ph-CHO

28. Stephen's Reduction (i) SnCl2 + HCl (ii) H2O RCN ---------> RCHO

T
Must have α H; Can dehydrate easily; LDA will pick
29. Aldol Condensation Dil NaOH Ald/Ketones -----> β hydroxy Ald/Ketones most acidic H (100% enolate formation no self aldol)
while NaOH will form stable enol

30. Claisen Condensation

31. Dieckmann Condesation

RONa
[II (Intermolecular Claisen)
2 α H are required. If only 1, then stronger bases like
NaH,KH,NaNH2,Ph3CNa are required
ru
32. Perkin Condensation Aliphatic Ald do not give this rkn (They have α H)
Ti
 ranjan_tatsam

Nu attack on second CHO-Ph is RDS so, -CN will attack

33. Benzoin Condensation Alc KCN
on the more activated ring first.

]
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Disproportionation rkn; there shouldn't be any α H. RDS
34. Cannizaro Reaction conc NaOH R-CHO -------> RCOO- + RCH2OH
is transfer of hydride ion.

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Stereoselective - trans > cis
35. Wittig Rkn Ph3P=CH2 Regioselective - better than E2 (Double bond in just one
place)

D
36. Tischchenko Reaction Al(OR)3 RCHO -------> RCOOR

T
37. Knoevenagel Condensation

38. Reformatsky Reaction

[II It is like Grignard, but much weaker so that it does not
react with ester

Meerwein Ponndorf Verley (MPV)

39. Al[OCH(CH3)2]3 + CH3CH(OH)CH3 Redeuce Ald/Ketones to Alcohols (especially in presence of NO2, C=C etc.) Reverse rkn is called Opeenauer Oxidation
Reduction
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{ H > 3 > 2 >= Ph > 1 > CH3 } Migratory Aptitude for the
40. Baeyer Villiger Oxidation peracid like mcpBA group that will get attached to O (i.e. R2 has a greater
MA than R1)
Ti
 ranjan_tatsam

41. Diel's Alder Reaction

]
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Yield of RX : 1 > 2 > 3
42. Hunsdiecker Reaction Br2 + CCl4 + Heat If RCOOAg and I2 are taken as 2:1 then ester is formed
and in 1:1 R-I is formed (Simonini Reaction)

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43. Hell Volhard Zelinsky reaction Red P + X2 + Heat

Intermediates : RCONH- RCONHBr -----> [RCONBr]-

D
-------> R-N=C=O (Ketime)
Hoffman Bromamide Degradation
44. NaOH + Br2 N loses both its H
(Rearrangement) no Cross only self
Only 1degree amines

45. Lossen Rearrangement (Same as Hoffman, in place of Br- we have -OCOR)

T
46. Curtius Rearrangement (Same as Hoffman, in place of Br- we have -N2+)

47. Gabriel Pthalimide Reaction

48. Sandmeyer
CuCl + HCl
CuBr + HBr
[II On Benzene Diazonium salt to get halo/cyano benzene
Only 1 degree amines
No Aromatic amines

CuCN

Cu + HCl
49. Gatterman
ru
Cu + HBr On Benzene Diazonium salt to get halobenzene

50. Balz Schieman Reaction HBF4 + Heat Benzene Diazonium to Fluorobenzene

(i) HCN
51. Kiliani Fischer Synthesis (ii) H3O+
Ti

(iii) Na-Hg (pH 3 to 5)

 ranjan_tatsam

Arndt Eistert Reaction (Includes Wolff

52. {O = C = CH - R} ---- Ketene is formed
Rearrangement

]
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 W
AMINES
A
1 Nomen clafkse CH NH, melhanamine
CH3-NH- C N methylenclhananine
N, N-imehyl methanamine

NH NH2
Hniline Tolui' dine

NHp NH,) pNi (Ss )a- NU Nta NF

lo7A l03 120 6-2
prefer
)FetHt n tHt, ZntH , Fndty 1Ht
g. RND 2)H2 tatatyt RNH
3 itty CH
NHyHS
CHNo NO2
NO2 NH2 Na,s

NS NH2
NO NO NO Snttz O
ONH
HO
NO
OH NH2 NH2
OH
NO2 NH2 No. NH O 2
NHyHS
N0
NO
NO
N02 NH2
alk FtSOy oo
nd TH
CHo) (CHO
LAHu tT H2tN;-
4.R-CEN_ >RGH, NH,
TNa tp/Gtgo
5 R-X
RX
R,NH >RN RN

NHz (extess)
6 Gabriels Phtlalinmide nthS
(OD
koHRXX +Nt-R
Coo
phthalimide
D

NH, NH2 [OKCNH +NH, R

N-R

7HoHmann bromamule deg vadalhen

R--Nt, t 1 NaOH B r RNH, T Na, w t Naby1ih0

Rearrangeneul K 1R= -OCH, > H2> H> >Wo f

enly IntamolewlayNo (yoSS
infhemol SN etenlfen if R is dural)
*TnfermedielCd R-N-6Y R--NHBr R-N
R-C-N: nifrene R-N= C=0 alkRyt SoCyonale

N apne dene H Leoe Rata ha

R-
R-C NH2 R- ND,
Naob, bo Hho
0 C N-R
usdiuo R- - N-NEN
RoH
I
ooen R--N
N0iR_ R-NH-C-NH-R Ro-c-NHR
Urea derivaffe tqroarnate
 8 DiSn audhing 7eals
)
4 RNH2 aRNH 3 kN RemarR
Regpenet
A)HNO Na 1 -nitroso amlne X NO
NR2
CT
Yaso
SH
X
B)Hoffmann munda as B,N-
oil kni)Cs) blatkppf
+RNCS pyme
Muolay &mll

Hoftmam
cthaodé-oE Selicl X
-0

e
D)[Link] RNO, R,N-OH&,-
POattdo)

ECaabylamine RNC X arbone

Unpleag en infesmecli'ate
(CHL, tKOH)
douy

P hS 0 2 N R Ph-502NR
PHinSbux Teor PP pt (R) e taRe
h Ht HT NK3 exeo
Ph-SoYe)
Bunzo Gulphony PP xxx denr ol
Ph-S0,-NHR (R NH) N-SoPh Ph
Chlonde R

8aaics 1 alkali Soluble

2 alkalinsoluble WRyt R,N sa Ph
HtPPf
3 X XXX
 Diazoffzalien OH
NH2
NaNo, t Ha
N H
A
0-5C)
EtoH P
KI

JanduWyey Ph-I +CH CHO tHPog

CuCe uBr
He KCN Her
Ph-CL Ph-Bx Ph-N
N,Bf
koi ek &mijhle
O
u Sondmayer Calteomann NaNO2
u an. u poudeT
u uoter
Ph-t Ph-t Ph-F NO2
+TN
batz Smemam ma Sala
kn

[Link] Ph-N ad ad Ewth 4=Nt,/NRH/NR

OH

Nt OH
PHET2 13,
Ph-o p-Hydroy 02pbeng nt Orange dye

NtHNH2 N N Ni
P-ammoa ze benZerne yellew dye
OH
oH Me me N Me

Me
SoNa methy orange
 PAGENo
DATE: I201

NH2
NH2 NH2
HNO3 BY2 NH2Br
H
NO 47 / NH2 Br whe pP
5R ( NHPh mala)
NH--Ha
NH2 NH2
NHa HSOy
H2y
ermajps)
25C
NH2 NH2 To
get 0 prpduct
SOaH Uuphianil'e block pava by Se H,
aud then hy droy se
SogH

NH2 FCA NH,- Ra3

XXX Pformo SD Gyp
e

13 No aweak e Con pm _hew EAS

with

Ph- C-
YY
Ph-C - NH-H
CBenzoylaton O

IS
R-NH, + R-C R-NF-R+ H
Pvidine wwd which enaunned He G_foswaz.
Ti
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 Date

CoOH
NO IDS Page No.

NH Serin - H2OOH

Aroine mreenive CH
0 Guind - H
Sif aa yrosine OH

Alanine
petlo, kat ae qulabjamun
P G
ysfen - CH,-SH

-C
Ag enfna zanori hai 5Methionine
Valin Aginine a .

yine
-CC 10 nen tao.
Avginine NH

12 ty H-NH- NH,
Prolinc NH
COOH
C
Pheny Alanine
Hisfdine NH,=-H=00H-
Tro sin
CH
Aspare Add CooH NH

Gutamic Aad 1 , 1, ooH

ASpaYagine CHl -N2

Typophan COoH

NH
Gufamina H

NHa
Ti
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Ti
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