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W
K

? ? ?
K?

W
K

KK

K
K


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W
W
K

W
K
W
K
W
KOverhead Projector
K
W
K

--

WJ
K
Organic

1828 WohlerK
EF

NH4OCN

H2N

NH2

K
K

--

KFunctional Groups

EOHF K

Ksp3

WFunctional Group J

K
O

O
O
CH3C H

[H]

CH3 CH2C H

[O]

[O]
[H]

CH3C-OH
CH3CH 2OH

( )
( )

CH3CH2COOH

( )

CH3CH2CH2OH ( )

--

[O]

O
CH3CH2CH2C H

[H]

CH3CH2CH2COOH ( )
CH3CH2CH2CH2OH ( )

( -CHO)
K

KEJ F

WEJ F

H2C

CH2

H
Br

EF

H C C

C= C

CH3I ,

CH3CH 2OH

C C

--

( X = I, Br, Cl , F )

C OH

CH3 O

CH3

CH3 C H
O

H C OH

CH3 C OCH 3

CH3

CH3NH2 , CH3NH

NO 2

O
C H
O

C C

C OH
O

C Y
( Y = Cl ,OR, NR 2 ,...)

C N

O
C N O-

CH3SH

CH3CN

CH3 C CH3
O

CH 3NO 2 ,

C SH

WJ
KEF

?hemolytic?K
K
?heterolytic?
K X

--

.
C. + X

C . .X

" "

C . .X

C + + .. X

carbonium ion
C . .X

C .. + X +

" "

carbanion

X
K

KXEF
KXEF

EF
KNucleophilesENu-FElectrophilesEE+F
F

WKE
--

H+ , Br+ , NO2+ , BF3 , AlCl3

F
WKE

. ._.
. . _.
. ._
. ._
..
. , RS .. , CN .. , H2O .. , R2N ..
HO
.
,
RO
..
..
..

substitution J
K

CH 3CH2OH + HBr

EF

CH3CH2Br +H2O

Waddition J
K

CH2

CH2 + Br2

CH2BrCH 2Br

EF

eliminationEF J

CH3CH2Br + NaOH

KE

CH 2 CH2 + H2O + NaBr

EF

--

WW

CH2OH

CH 3C N(CH 3)2

CH3

CH3CH 2F

CH3 Pb

CH3

CH3

CH 3OCH 2CH 2C H

CH3CH2 , ZnCl2 , F , CH3CH2 , CH3OH , CH3SH , CH3NH2

WW
O
a) - CH3 C H + CH3MgI

CH3CHCH3
OMgI

b) - CH3CH2I +

CH3CH2SH + NaI

NaSH

c) - CH2 CH CH3 + HCl

CH3CHCH 3
Cl

--

J J J J

W
KWCH3NH2
KWCH3OH
KWF KW

ZnCl2

KW
K

--


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W
J W
K .

K .
EF .
K

W
K
W
K
W
KOverhead Projector .
K .
K .

K .

W
K

- -

W
WJ

K
W

saturated K
Ethane CH3-CH3alkanes
J unsaturated K
W
EC=CFalkenes J

EC C Falkynes

K
Aromatic Hydrocarbons J
K C10H8

WAlkanesJ

- -

nCnH2n+2W

KEnFEKKKKKKK{{{=nF

K
WJ J

E-aneF

E-aneFE F
EJ F

EJ F
n

CH4

methane

ethane

propane

butane

5 pentane

hexane

heptane

octane

nonane

10

decane

CH3CH3
CH3CH2CH3

CH3CH2CH2CH3
CH3(CH2)3CH3
CH3(CH2)4CH3
CH3(CH2)5CH3
CH3(CH2)6CH3

CH3(CH2)7CH3
CH3(CH2)8CH3

- -

CH2
Methylene
W

Butane C4H8W
CH3 CH CH3

CH3-CH2-CH2-CH3
n-Butane

CH3

IsobutaneJ

Pentane C5H12

CH3 CH CH2 CH3

CH3

Isopentane

CH 3

CH3CH2CH2CH2CH3

N-pentane

CH 3

CH3

CH 3

Neopentane

WAlkyl Group ER-F

ER-F
methylCH3-

E 2-2FKEthylECH3CH2-F

- -

KJ

Methyl

CH3J

Ethyl

CH3CH2-

MethaneCH4
Ethane CH3CH3

CH3CH2CH2-

N-Propyl
Isopropyl
n-Butyl
sec- Butyl

CH3-CH-CH3
CH3CH2CH2CH2 CH3CHCH2CH3

Propane
CH3CH2CH3
CH3CH2CH2CH3
n-Butane

CH3
Isobutyl

_
CH 3 CH CH 2

Tert-butyl

CH3

CH3 C

CH3

CH3 CH CH3

Isobutane

CH3

Cycloalkanes
W
CH 2

- -

CH 2
CH 2
Cyclopropane

CH2

CH2

CH 2 CH2

Cyclobutane

CH2

CH2

CH2

CH2
CH2

Cyclopentane

CH2CH3

Ethylcyclopropane
WIUPAC

IUPAC W
International Union of Pure and Applied Chemistry.

W
EF

EF EJ F

ane
Wyl

- -

CH 3CH 2 CHCH 2CH 2 CH 3

CH 2CH 3

3-Ethylhexane
E
F

penta tetratridi

KKKKKK

CH3
CH3 CH CH2 C CH
3
5
4

CH3

CH3

2-2-4-Trimethylpentane

CH2CH3

CH3 CH2 CH2 CH CH C CH2 CH3

_

CH3 CH2 CH2 CH3 CH2CH3

3,3-Diethyl-4-methyl-5-n-propyloctane

W
7

CH 3 CH 2 CH CH 2 CH

CH 3

CH 2CH 3
- -

CH 2 CH 3

3-Ethyl-5-Methylheptane

EF

EaneFEylF

1'

CH3 CH2
1

CH3 CH3
2'

CH CH CH3
3
CH CH CH2 CH2 CH2 CH3
CH2

CH2CH3

CH3

3-Ethyl-4(1',2',Dimethylpropyl) nonane

EF

K
WE
NO2W Nitro

F: Fluoro

ClW Chloro

NH2W Amino

BrW Bromo

CNW Cyano

IW Iodo

- -

Br

W
2

CH3CHCHCH 2CH3
3

CH3

Cl

3-Bromo-2-chloro-4-methylpentane

neo-iso-

tridisec-tert-

WJ J
nonpolar

C4C1

C17C5

EF
K

WJ J

W
Wcombustion

KK
- -

CH4 + 2O2

CO2 (g) + 2H2O +

(g)
WHalogenation

Br2Cl2EF

W
WEF
Br
+ Br2

+ HBr

Bromocyclopentane

WEF

H
H

H3C _ Cl + HCl

H + Cl2

H
h

CH3 Cl + Cl2

Chloromethane

CH2Cl2 + HCl
Dicarbomethane

CH 2Cl2 + Cl2

h
hv

CHCl 3 + HCl
Chloroform

- -

hv

C H Cl 3 + Cl2

C C 14 + HCl
Carbontetrachloride'

W
KEF

H 2 /Pt ,Pd Ni

C C

H H
Alkane

Alkene

CH3CH2CH2CH2CH = CH 2
1- Hexene

H2 , Pt

CH3CH2CH2CH2CH2CH2
n- Hexane
W K

KGrignard reagents
K
R-X + Mg

Alkyl halide

- -

RMgX

Alkyl magnesium halide

R-MgX + H 2O

RH + Mg(OH)X
Alkane
RH + Mg(OCH 3)X
Alkane

RMgX+CH 3OH

Br

Mg Br

CH3CH2CHCH 3+Mg

CH3CH2CHCH 3
H2O

Mg(OH)Br + CH 3CH2CH2CH3

W K
K

2R - X + 2 Na

R - R + 2 NaX
Alkane

2 CH 3 CH2 Cl + 2 Na

CH3 CH2 CH2 CH3

W K

WLithium dialkyl copper ( R2CuLi)

(CH 3 CH2)2 CuLi + CH 3 CH2 CH2 Br

CH3 CH2 CH2 CH2 CH3 + CH3 CH2 Cu + LiBr

- -

W
CH 3 CH2 Cl + Li

CH 3 CH2 Li

(CH 3 CH2)2 CuLi + Lil

2 CH 3 CH2 Li + Cul

WJ J
K
K

K

KRefining

- -

WalkenesJ
EC=CF

CnH2nolefins

KC2H4CnH2n-2

120

C
H

C
H

WJ J
W K

ylenealkane ane
W
KE1-3-2F
Alkene

Ethylene

Propylene
Butylene

B-Butylene

Alkane
Ethane

CH 2=CH 2

CH3-CH =CH2

Propane

CH3CH2CH=CH2

CH 3CH 2CH 3

CH3CH=CHCH3

n-Butane

Isobutylene CH3 CH = CH2

CH3CH3

Isobutane

CH3
- -

CH 3CH 2CH 2CH 3

CH3 CH CH3
CH3

CH2=CH2

W( Vinyl group )CH=CH2

CH 2 = CH

CH2 = CH
Cl

CH2 = CH

Br

Vinyl Chloride Vinyl bromide

Vinyl Cyclohexane

W( allyl group)CH3CH=CH2

CH2CH = CH2
Cl

Allyl Choride
WIUPAC K

E FIUPAC

KEF E
ane E

Kene

E
K

- -

CH3CH-CH = CH-CH 3
CH3
4- Methyl - 2- Pentene

CH2 = CH2

CH3CH2CH = CH2

CH 3 -CH = CH

Ethene

1-Butene

Propene

CH2-CH = CH2
Cl

3-Chloro -l- Propene

2-Ethyl-1-Butene

K
6

4
5

Cyclohexene
(1-Cyclohexene)

2
1

3-Methylcyclohexene
(6-Methylcyclohexene )

eneKKKKKKtetratri di

- -

CH2 = CH-CH 2-C-CH 2CH3

1 CH 2

2-Ethyl,1,4-Pentadiene

2
1

1,3-Cyclopentadiene

6

4
3

1,3,6-Heptatriene

E2-butane 1-butene
K

W2-butene

CH3

CH3

H
C

CH3
C

CH3
H
trans-2-butene

H
Cis-2-butene

EF

FE
cisF

KtransE
trans-2- cis-2-butene

K {butene

- -

WJ J

WJ J
W
W

H+

KH3PO4H2SO4

H ,

H
C

+ H2O
H

OH H

( )

( )

F
E
W

CH2

CH

CH CH3

OH

2-Butanol

H ,

CH3-CH = CHCH3
2-Butene
+ H2O

CH3=CHCH2CH3
1-Butene
- -

KKOH( I , Br, Cl =X ) HX
CH2

CH2

Cl

KOH /

CH2 = CH2 +K +CI +H2O

CH2

CH

CH

Br

CH3

KOH /

CH3

CH = CH

CH3 + K+

J EFJ

H+Br-+H2o

CH2 = CHCH2CH3

EFJ
W H2SO4 K

K

K

- -

CH2 = CH2 + H2SO4

CH2

CH2

OSO3H
H

WPolymerization K

Kpolymers
K

WW
Naphtha fraction

J
J
K

ECr2O3+Al2O3)
K

CH3CH2CH3

Cr2O3 +Al2O3
700c

CH2 = CHCH3

W( X = Cl ,Br, I ) HX

- -

+ HX

H X

CH2=CH2 + HCI

CH 3

CH2 CI

( )

KMarkovnikov's Rule
CH2 = CHCH3 + HCl

CH2

CH

Cl

CH3

WHydration

KH+

K
CH2 = CHCH3 + H2O

CH2

CH

OH

CH3

- -

WJ J
K
WK
WHydrogenation .
KCatalystsEFPdNi Pt
CH2 = CH2 + H2

Pt or Ni

CH3 CH3

WHalogenations .

X2 / CCI4

(X = CI , Br)

CH2 = CH2 + Br2 / CCI4

CH2
Br

CH2

Br

EF

- -

WAlkynesJ
J F

CnH2n-2KEJ C C
spC2H2

CaO

KCaS2

3C + CaO

2500 oC

CaC2 + 2H2O

CaC2 + CO
C2H2 + Ca(OH) 2

WJ J
EIUPACF

Wene yne

HC

CH

Acetylene
Ethyne

CH3C

CH

Methyl acetylene

Propyne

CH3CH2C

CH

Ethyl acetylene

1- Butyne

- -

WIUPAC
CH3

CH3

CH3C

CCH3

2-Butyne

CH3CH CH

C CH2CH CH3

Cl
3-Chloro-2,7-dimethyl-4-octyne

CH

CH

1,3-Butadiyne

yne
Kalkene
HC

CH CH2 CH CH2
1-Penten-4-yne

Kyne

WJ J

K

C17C16C4 C4C2
K

- -

WJ J

Dehydrohalgenation W .

KOH

CH3CH CH H

[ CH3CH = C

EtOH

Br

Br Br

Allylbromide

1,2-Dibromopropane

CH3 C

H]

NaNH2 /

Propyne

W .
W
HC

C Na+ + CH3Br

HC

C Na+ + CH3CH2I

CH3 C

liq NH 3

liq NH3

liq NH3
C Na+ + CH3CH2Br

Sodium propynide
- -

HC

HC

CH3 + NaBr

C CH2CH3 + NaI

CH3 C

C CH2CH3 + NaBr

K
W

W
W J
W

CH4 + O2

2HC

CH + 2CO + 10H2

W J

EF

CaO + CO2

CaCO3

Calcium carbonate
CaO + 3C

2500

CaC2 + CO

Coke

CaC2 + 2H2O

C
25

Calcium carbide

HC

CH + Ca(OH)2

Acetylene

- -

WJ J
W

WK
W .

R
R

R + H2

Pd or Ni

R
C=C

H2\Ni

RCH2CH2R

Ni-


Linders

catalyst

Pd + Pb(OAc)4B2

KPd/CaCO3)

W .

Cl
CH3 C C CH3 + Cl2

CH3 C = C CH3
Cl

Cl Cl
CH3 C C CH3
Cl Cl
1,1,2,2-Tetrachlorobutane

- -

W .

K
Cl
CH3 C

CH

HCl

CH3C = CH 2

HCl

CH3 C

CH3

Cl

Cl

2,2-Dichloropropane

W .

mercuric sulfate
K

CH

CH + H2O

HgSO4
H2SO4

CH3 C

C=C

Acetaldehyde

OH
CH + H2O

HgSO4
H2SO4

OH

H
Enol

CH3 C

CH3

C = CH2

O
CH3 C

CH3

Acetone

- -

W .

W
O O

1)KMnO4 /OH
2)H2O / OH

1)KMnO4 /OH
2) 100
C/H +

R
-

1)O3
2)H2O /Zn Or H2O2

OH + R C

RCOOH

OH

+ RCOOH

J J

(PVC)
A
K

KPayragyline

- -

2-5

WIUPACJ

CH3CHCHCHCH 3

Br Cl CH3

CH3-C(CH3)2CH3

CH3

CH3CH2CH2 C = CH2

J
CH3

C2H5
CH C

CH

CH3
CH3 C = C

CH3

CH3 Br

J
J

2-bromo-2-methyloctane

2,3-dimethylbutane J

2-chloro-3-methyl-2-pentene J
1,1-dimethylcyclohexane J
2,2-Dibromo-3-hexyne J 2,3Dimethyl-1,4-cyclohexadiene J

C6H14

- -

W
J

CH3CH3 + Cl2
CH4 + 2O2

CH3CH2Cl + Na
CH3CH2OH
CH3CH=CH2

J
J

H+,

Pt or Ni

CH3CH=CHCH3 + Br2

CCl

CCl4

+ Cl2

CH3CH CH CH3

J
NaNH2 /

KOH

EtOH

Br Br
CH3 C C CH3 + 2Cl2

CH3 C

CH

HgSO4
H2SO4

J
W

i) CH3CH3

ii) CH3CH2Cl

iii) CH2 = CH2

W
3-Bromo-1-pentyne ,

4-Methyl-2-hexene

W
H2 , Br2/H2O , H2O/H+ , HCl
- -

W
2,2- Dimethyl Propane -

3-Ethyl-1-Methyl cyclohexane -

3-Methyl -1- butyne -

2- Bromo -3-Methyl -2- buteneJ

W
.
CH3 - CH -CH -CH3
CH3 CH3

CH 3 C

CH 2CH 3

Cl CH 3

Br
CH 3 C

CH 2CH 3

Br

.
KW

W
CH4 +2O 2

CO2 + 2H2O +

. J K

CH3 CH2 OH

CH3 - CH = CH - CH 3 + Br2

H ,

CCI4

CH2 = CH2 + H2O .

CH2CH - CH CH 3
Br

- -

Br

J K
J K


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W

K

W
W
K .
K .

K .
K .
W
K
W
K
W
KOverhead Projector .
K .
K .
W
K

- -

W1J 3

K
EFEAromatic)
J OCH3

J C6H5J J J J J COOCH3J COOH

J C6H5
EF
K

W2J 3
C6H6
K

Ksp2
(AF

KEA)C-CEA)C=C
WKekule

I
II
HybridKIII
KIII
Delocaized

- -

W3J 3
W
K
FPEF
KE

K K
K K

EHuckels ruleF K
En = 0,1,2,3KKKKKKKFE4n+2)

EF

WEFEFn

(4x1+2) = 6

EF

Benzen
n =1

Naphthalene
n =2

- -

Anthracene
n =3

Phenanthrene

4(1)+2=6 es

n=0
4(0)+2=2 es

N
..
Pyridine
n =1

n=3
4(3)+2=14 es

n =1
4(1)+2=6 es

..
N
Pyrole
n =1
4(1)+2=6 es
+

n =1
4(1)+2=6 es

W4J 3
K
{

- -

W4J 3

W

W K
W

Bromobenzene

CH2CH3

Br

Iodobenzene

Ethylbenzene

NO2

Nitrobenzene

CH3

Toluene

OH

Phenol

CH=CH2 CH _ CH _ CH
3
3

CHO

Styrene

Cumene

COOH

Benzoic acid

- -

O
C _ CH3

NH2

Acetopnenone

Benzaldehyde

Aniline

OCH3

SO3H

Benzenesulfonic acid

Anisole

Kphenyl

CH2CH2OH

CH3CHCH2CH3

2-Phenylbutane

2-Phenylethanol

Benzyl

Benzal

KBenzo

CH2Cl

Benzylchloride

CHCl2

Benzalchloride

CCl3

Benzotrichloride

K
ortho EOFK
meta EmF
- -

K para Ep F
K Benzene K

W
CI

CI

CI

m-chloroethylbenzene

O-dichlorobenzene

p-fluoroiodobenzene

COOH

CH 3

CH2CH3

NO 2

OH

o-chlorophenol

Br
m-bromobenzoic acid

m-nitrotoluene

CI

WCH3-
CH3

CH 3

CH3

CH3

o-xylene

CH3

CH 3

p-xylene

m-xylene

NO2

CI

CI 1

CI

1,2,3-trichlorobenzene

CI

3-chloro-5-fluronitrobenzene

F
E

(1,2,6-trichlorobenzene)

- -

OH
Br

CH3

Br

NO2

Br

NO2

NO2

2,4,6-tribromophenol

2,4,6-trinitrotoluene (TNT)

WJ

K
_
Al2O3 CrO3 / 500 C

CH3(CH2)5CH3

CH3
+ 3H2

Pt / 400 C

Toluene
CH3

Al2O3 _ Pt

+ 3H2

550 C

Benzene

- -

WJ

K
W .

W
WHalogenation K

EF
EF

K
CH2Cl

CH3

CHCl2

Benzoal
choride

Benzoyl
choride
CH3

Toluene

Cl2
/

Cl2
/

CI2
/

Cl2/FeCl3

CCl3

Benzotrichoride
CH3

CI
+

o-chlorotoluene
- -

Cl
p-chlorotoluene

W K

CH3

COOH
KMnO4 or
K2Cr2O7

Benzoic acid

CH2CH2CH3
CH3
KMnO4 or

COOH
COOH
+

K2Cr2O7

(CO2 + H2O)

Phthalic acid
( 1,2- benzenedicarboxylic acid)

W .
W -

EthylbenzeneK

KCyclohexane

CH 2CH 3
+ 3H 2

Ni,Pt or Pd

CH 2CH 3
Ethylcyclohexane

Ethylbenzene
- -

W
EF

W
Alkylation EF J

+ CH3Cl

AlCl3

CH3
+ HCl

AcylationEF

O
AlCl 3
_
_
+ CH3 C Cl

O
C _ CH 3

Halogenation

+ Br2

FeBr3

- -

Br

Nitroation

+ HNO3

NO2

H2SO4(conc.)

+ H2SO4

SO3H

SO3

Sulfonation

WJ

AnisoleK

K nitroanizole
K
OCH3

OCH3

OCH3
NO2

HNO3
H2SO4

NO2

K
NO2

NO2
HNO 3

H2SO4

- -

NO2

=OR+F
EH+Br+NO2+CH3C+

.
W
-NH2(-NHR,-NR2) ,-OH >-OR,-NHCOCH3 > -C6H5 ,-R

KERF
K .
E-F,-Cl, - Br )

WK .
K-NO2, -N+(R)3,-C=N,COOH( -COOR ),-SO3H,-CHO,-COR

- -

NO2

NO2
Br2,Fe

HNO3
H2SO4

Br
Br

Br2,Fe

m-bromonitobenzene
Br
NO2
HNO3
+

Br

H2SO4

NO2
p-bromonitro
o-bromonitro
benzene (38%) benzene (62%)

WJ

KEF

KEF

K
K

- -

WW

CH = CH
Br

a)

COOH

CH3

c)

b)

NO2

CH3

CH3

d)

e)
I

COOH
CI

NO 2

WW
a) 1,3,5-trichloro benzen

b) m-bromotoluene

c) p-bromoniro benzene

d) lsopropyl benzene

e) 4-bromo-2,3-dinitrotoluene

f) m-chloro benzoic acid

WW

CH(CH 3)2
KMnO 4 / OH

CH 3

Br 2 /hv

- -

NO 2

Br 2
FeBr 3

OC 2H5
AICI 3

+ CH 3CH 2CI
CI
O
+ CH 3 C - CI

AICI 3

CH 3
H 2O 3
HNO 3

+ CH 3 CHCI CH 3

AICI 3

CN
Br 2
FeBr 3

- -

W
O-Bromostyrene J
3,5- Diiodo tolueneJ

W
CH3

Br2

CH (CH 3)2

CH(CH 3)2
KMnO 4/OH

COOH

NO2

NO 2
Br 2

FeBr 3

CH3

CH3
HNO2
H2SO4

Br

NO2

CH3

+
NO2

+ CH 3 CHCI CH 3

AICI 3

CH (CH 3) 2

- -


]<gj]<]<j<^]<]

W
W
K .

K .
K .
W
K
W
K
W
KOverhead Projector .
K .
K .

W
K

- -

1J 4

RR - X

K
2J 4

K

KW

FAlkyl

EFIUPACE
W

CH3Cl

CH3CH2CH2Br

(Methyl chloride)

(n propyl bromide)

Chloromethane

1 - Bromopropane

1 halides

CI

I
CH3 - CH - CH3
EIsopropyl iodide)
2- Iodopropane

2halides
(Cyclopentyl chloride)

Chlorocyclopentane

CH3
CH3 - CH2 - CH2 - C - CH = CH2

CH3
CH3 - C - CH3

Br
Br
3-Bromo-3-methyl-1-hexene (tert-Butyl bromide)
- -

3 halides

W
_
CH2 = CH CH2
X
Allylhalide

CH2 = CH
X
Vinylhalide

CH2X
Benzylhalide

W
CCl4
(Carbontetrachloride)
Tetrachloromethane

CHCl3
(Chloroform)
Trichloromethane

CHBr3

CHI3

(Bromofoem)

(Iodoform)

CH2Cl2
(Methylene chloride)
Dichloromethane

Br
CH3 - C - CH2CH3
Br
2,2-Dibromobutane

3J 4

FK
KE

- -

3J 4


W

EF .

K
CH3CH3

Cl2

CH3CH2CI + HCI + ...

UV or heat

CH3 - CH = CH2

Br2
UV or

CH2 - CH = CH2 + HBr

Br

W
CH3 - CH = CH2

HCl
CCl4

CH3 - CH - CH3
Cl

W
CH3-CH = CH2

HBr
R-O-O-R

CH3CH2CH2
Br

- -

W
HCl

CH CH
CCl4

CH2 = CH

HCl
CCl4

CH3CHCl2

Cl

EF .

HX

WEPCl5 , PCl3 , PBr3FSOCl2

CH3(CH2)5 CH2OH

HCl
ZnCl2 / 150

CH3(CH2)5 CH2 +H2O

Cl

NR 3

CH3CH2OH + SOCl 2

CH3CH2OH +PBr3

CH3CH2Cl + SO 2 + HCl

CH3CH2Br + P (OH)3

5J 4

KEF
KEF
KKKK
Nucleophilic substitution reactions K

EF
- -

W
R3C+-

R3C-Nu +

W
-

SR , SH , CH3NH2 , NH3 , - O - C - R , OR ,OH

..
N (CH3) 3 , HN (CH3)2 ,
CN ,R - C = C

CH3CH2CH2Br

KOH
H2 O

CH3CH2CH2OH

Elemination reactionsEEFEF K

KEF
+
KOH (Or) CH3CH2O Na
_
CH3 - CH = CH2
CH3CH
CH3
EtOH /
Br

- -

-4

Grignard formation K

K
CH3CH2CH2Br + Mg

ether

CH3CH2CH2MgBr

K
K
W
- +
CH3CH2CH2 Li + LiBr

CH3CH2CH2Br + 2Li

K
J

KD.D.T.
H
Cl

Cl

CCl 3

D.D.T

[CF2CF2]nTeflonW
[H2CCl2]n

K[CH2 CHCl2-]nPVC K
- -

CCl3FCCl2F2CF3CHClBrHCX3haloform

K
AntifungusAntibiotics

EIUPAC FW

Br

CH3CH_ CH _ CH3

E
_
CH CH3

_
_
CH 3 CH2 CH=CH 2
Cl

CH2 = CH CH2Cl

Cl

NO2

Br CH3

E
E

E3 21FW

Cl CH3

CH3
CH3 C CH3
Cl

Br

KW

CH3

HCl

CH3CHOH ZnCl
2
CH 3

HBr

E
- -

CH3

Cl2
hv

CH2CH3

SOCl2

OH

+ _ CH Na O CH2CH3

CH3CH2CH
Br
Br
CH3 C CH2

KOH
EtOH
NH2CH3

CH 3CH 2CH 2Cl

CH 2CH2Br

Br

3 CH3CH2OH

CH3

CH 3CH _ CH 3

Br2
hv

CH3CHCH3

CH3C

E
-

C Na

KOH
EtOH /

CH 3CH 2CH 2Br + Mg

E
E

ether

WW

OH

CH 3CHBrCH 3 ethanol
-

OH
CH 3CHBrCH 3 H2O
-

(CH 3)3CBr
(CH 3)3CBr

CN
ethanol
H2 O

- -

2-Bromo-3-methyl butane

1-Bromo-2-Nitro cyclohexaneJ

1-chloro-1-buteneJ

W
CH3

HCl

CH3CHOH ZnCl
2
CH3
CH3CHCH3

CH3
CH3CHCl + H2O
CH3

Br2
hv

CH3 C CH3
Br
NH2CH3

CH3CH2CH2Cl
KOH
CH CH_ CH
3

Br

3 EtOH /

CH3CH2CH2NHCH 3
CH 3CH=CH 2 + HBr

E
E
E

J
J

- -


]<gj]<]<j<^]<]

W


K

W
W
K .
K .

K .

W
K80
KW

W
KOverhead Projector .

K .
K .

W
K

- -

W5J 1
J OH

ArOHROH
Ar
RArR

SP3
KSP2

K
K

W5J 2

Tertiary 3

Secondary 2

Primary 1O
H

R
OH

OH

OH

J OH J OH J OH

- -

KR

W5J 3
KIUPAC
K
W K
W

CH3 OH
Methyl alcohl
CH3
CH3

CH3CH2OH
Ethyl alcohol

CH3
CH3

CH

CH2=CH-CH2OH
Allyl alcohol
CH3

OH

OH

Isopropyl alcohol

Tert-Butyl alcohol

CH2OH

OH

Cyclopentyl alcohol

Benzyl alcohol

WEFW K

OH

EeF
WKJ

CH3OH

CH3CH2OH

- -

ol

Ethanol

Methanol

-OH

WEF

CH3CH2CH2CH

CH3

CH3CH2CH2OH

OH
2-Pentanol

1-Propanol

C 2H 5

OH

CH3CH2CHCH2CHCH3
OH

Cyclohexanol

4-Ethyl-2-hexanol
CH2CH2Br

CH3CH2CH2CHCH2 OH

2-(2-Bromoethyl)-1-Pentanol

CH2CH3
CH2

CH

CH

CH

CH3

CH3CH
OH

CH2

CH3

OH

4-Methyl-1-Penten-3-ol

3-Ethyl-3-buten-2-ol
OH

CH

CH

CH3

OH
CH3

4-Methyl-2-cyclohexenol

3-Butyn-2-ol

- -

-ol tetra,tri ,di

KK

CH2

CH2

CH2

CH

CH2

OH

OH

OH

OH

OH

1,2-Ethanediol

1,2,3-Propantriol

Ethylene glycol

Glycerol or Glycerene

W

-OH

OH

OH

OH

Br

Phenol

m-Bromophenol

NH2

p-Aminophenol
OH

OH
COOH

OH

o-Hydroxybenzoic acid (
Salicylic acid)

Hydroquinone

- -

W5J 4

K
KEF

Ar

O
R

O
H

Ar

O
H

K
Ethanol

Propane

K
H

o
R

o
H

o
H

- -

W5J 5
W
K

K
H
+

CH3CH

CH2

+ H2 O

CH3

CH

CH3

2-Propanol

Propene

EthanolMethanol
W
water gasW K

KE F
O

C +H2O

1300 C

CO + H2

Water gas
K300 atm300c

CO + H 2 + H2

Zn + Cr 2 O3 as Cat.

CH3OH

Water gas

WNatural gas K

K900 Co

Ni as Cat.

CH4 + H2O

CO + 3H 2O

KSynthesis
CO + H 2O

ZnO + Cr 2 O3 as Cat.
O

300C , 300 atm.

CH3OH

- -

: Ethyl hydrogen sulphateCo

CH2

CH2 + H2SO4

CH3

CH2

OH

SO2

K
CH3

CH2

OH

SO2

H2O

CH3 CH2 OH + H2SO4

Phosphoric F

CoEacid on silca
K70 atm
W

K
- +
ONa

SO3H
NaOH

OH

HCl

Benzene sulfonic acid

Sodium phenoxide

Phenol

Propene Cumene E

AlCl3

K
CH

+ CH3

CH

CH2

CH3

Cumene
- -

CH3

Hydroperoxide
K
CH3
CH3

CH

+ O2

CH3

OH

CH3

OH

+
H

+ ( CH3 )2 C
Phenol

Acetone

K
W E
- +
O Na

Cl
Cl2

NaOH

330 C

40 C
Benzene

OH

Chlorobezene

Phenol

Sodium phenoxide

W5J 6
W
W -

K
H2SO4

2CH3CH2OH

(CH3CH2) 2 + H2O

140 C

Diethyl ether

Ethanol

CH3CH2OH

H2SO4
O

CH2

CH2

+ H2O

180 C

Ethylene

- -

W Oxidation
E1 F
K
W
CH3CH2OH

Cu/

CH3CHO

CrO3 or Pyridine

Ethanol (1)

CH3CH2OH

Acetaldehyde
3+

H2Cr2O7

CH3COOH + Cr
Acetic acid

OH
CH3CHCH3
o
Alcohol ( 2 )

O
H2Cr2O7

CH3

or Cu /

CH3-C-CH3
CH3

CH3

Ketone

O
Oxid.Agent

W -

K
CH3 OH

+ Na

- +
CH3 O Na + 12 H2
Sodium Methoxide

Methanol

- +

O Na

OH

+ Na

+ 12 H2

Phenol

- -

W -
K

K H+
O

(Ar)R

OH + RCOOH

(Ar)RO

R + H2 O

Ester

Alcohol or Phenol
+

CH3COOH + CH3CH2OH
Acetic acid

CH3COOCH2CH3 + H2O

Ethyl alcohol

Ethyl acetate

- -

EF

WE3 FE2 FE1 F

CH3 CH2 CH2 OH

CH2CH3

(B
CH3

(D

Br
CH3

CH

H2 C

CH2

(A

OH

CH2CH3

CH3

CH2

(C

CH2 OH

OH

W
OH

(B

(A

Br

CH3

OH

NH2

(c

OH

CH2OH

OH

CH3

OH

(A

CH

CH2CH3

CH3

OH

CH2CH3

O
(B

CH3 CH2 C OH

CH3 CH2 CH2 OH

OH

CH3OH

+
H

Cu ,

K2Cr2O7

(D

CH 3

W
CH3

H2SO4

(C

(D

OH
(E

- -

1) 2,4-Dimethyl-2-Octanol.
2) Cyclopentane-1,4-diol.

3) 2,2,2-Trichloroethanol.
4) 2-Butene-1,4-diol.
5) 3-Bromo-2-nonanol.
6) O- Bromophenol.
7) 2,4,6-Trichlorophenol
8) p-Hydroxybenzyl alcohol.

- -

EF
K3o

WE1F

1,1-Diethyl propanol

EA

1-Bromo-2-propanol

(D

. 2o

WE2F

4-Amino-5-bromo phenol

EA

EC

2,4,6-Trimethyl phenol

WE3F
KMnO 4
H2O

(A

(B

CH3 CH2 C O CH 3
O

(C

CH3 CH2 C H

WE4F

CH3
CH3-CH2-CH2-CH2-C-CH2-CH-CH3
CH3

(1

OH

CCl3-CH2-OH

CH3-CH2-CH2-CH2-CH2-CH2-CH-CH-CH3

(3
(5

Br OH

OH
Cl

- -

Cl

(7

Cl


]<gj]<]<j<^]<]

W
K

W
W
K .

K .

W
K80

W
K

W
KOverhead Projector .
K .

W
K

- -

W6J 1

R/RR-O-R/
WK

R/ R
K
W6J 2


Ether

CH3OCH2CH3

CH3CH2OCH2CH3

CH3OCH3

Ethyl methyl ether

Ethyl ether

Methyl ether

CH3

Methyl phenyl ether

Phenyl ether

( Anizole )

-O-RIUPAC
REAlkoxy)

WR(Aryloxy)

Br

CH3CH2CHCH3

o CH2CH3

oCH3

p-Bromophenoxy ethane

2-Methoxy butane

o CH2 CH3

Ethoxy cyclohexane

oxa
W K
- -

1
CH2

2
O

3 4
CH2 CH2

5
O

6
7
CH2 CH2

8
O

9
CH3

Cl

1-Chloro-2,5,8 -trioxanonane

W
O

Oxlane
or
Tetrahydrofuran

Oxane
or
Tetrahydropyran

O
1,4-Dioxane
or
1,4-Dioxa cyclohexane

( THF )

o
CH2

CH2

Oxetane

Oxiran e cepoxide
or
Ethylene oxide

or
Trimethylene oxide

K
W

- -

R
O

H
O

R
H

R
O
R

Ethanol

CH3CH2OH

o78

46

o24J

46

Methylether

o42J

44

Propane

CH3OCH3
CH3CH2CH3

W6J 3
F

E
K

EPeroxide) (F
K

Fe+++ FeSO4
W

- -

+++

Peroxide + Fe

SCN

Fe(SCN)3

F .
KE

K .

K .
W6J 4
WW
W
.
K
CH3CH2OH

H2SO4

140

K
CH3CH2OCH2CH3

W .

FEalkoxide ionF
KEphenoxide ion

CH3

CH

- +

O Na

+ CH3CH2Br

CH3

CH3

CH

CH2CH3

CH3

Ethyl isopropyl ether

- -

- +

O Na

O CH3

+ CH3Br
Anizole

WW
W .

K
WDiethyl ether .

W6J 5

K
+

CH3 CH 2 O CH 2 CH 3 + 2HI

2CH3 CH 2-I + H 2O
Iodoethane

- -

EF
W .

C6H5CH2

CH3 CH

C3 H7

CH2 CH CH3

CH3CH2CH2OCH2CH3E1

E4

(CH3CH2CH2CH2)2OE2

(5

O CH2CH3

CH3

CH3

(6

(3

CH CH3
CH3

O CH2 CH3

W .
1) Diisopropyl ether.
3) tert-Butyl methyl ether.
5) Phenyl ether.

2) Diallyl ether.
4) Benzyl ether.
6) 4-Ethoxy -2-Methylhexane.

W .
CH3

(1)

(2)

CH3

(1

CH2

CH3

O
CH3O + (CH3)3CBr

(CH3)C

+ CH3I

(3)

(2

(4)

(3

(CH 3)2CHCH 2OC(CH 3)3

HI acid conc.
with

- -

(5)

(4

K .
CH3CH2CHCH2CH2CH3

(2

CH3CH2CH2CH2CH2CH2CH3

(1

OH

CH3CH2CH2

CH2CH2CH3

(3

- -

EF
Dibutyl ether

(3

WE1F

Ethyl propyl ether

Isopropyl methyl ether

(1
(5

WE2F
CH 3 O C (CH 3)3

(2

(CH 3)2 CH O CH (CH 3)2

CH3-CH-CH 2-CH 2-CH-CH 3

CH3

(1

(6

O C2H5

WE3F
(CH3)3 C O CH 3
(CH3)3 C O CH 3

(2
(3

- -


]<gj]<]<j<^]<]

W
W
K .

K .
K .
W
K80

W
K
W
KOverhead Projector .
K .
W
K

- -

C=O

W7J 1

EArFR R(Ar)-C-H W
O

R , R R

W K

W7J 2
KIUPAC
W
WJ

J ic acid

aldehydeE F
K

O
H

Formic acid

Acetic acid

Formaldehyde

O
CH 3

Acetaldehyde

(C

- -

O)

W
CH3

CH2CH3

CH

CH

CH3

Dimethyl Valeraldehyde

WJ

F
WketoneE
O

O
CH3

CH3

CH3

Dimethyl ketone

CH( CH3)2

Methyl isopropyl ketone

( acetone )

Phenyl phenone

WE-oic acid F-ic acid

O
C

O
CH3

Acetophenone

Benzophenone

W
WJ

J alJ e
KK
K

- -

O
CH3

CH3

CH3

CH

O
CH2

Ethanol

3-Methyl butanal

K
O

O
C

Benzaldehyde

CH 3

p-tolualdehyde

J eEJ al FJ one

K
IUPAC

K
O
CH3

Propanone

CH3

CH2
Cyclopentanone

CH

CH3

3-buten-2-one

W7J 3

+ C=O

- -

K
K
O
C

Formalin

KE37F

56
K

W7J 4
W
W

K
O

CH3CH2CH2OH

Cu /

CH3CH 2C

Propanal

1-Propanol (1)

OH

CH3CHCH 3
o

H2Cr 2O7

+3

CH3C

CH3 + Cr

Acetone

2-Propanol (2)

W
- -

E

F
W
O

AlCl3

Cl

+ CH3CH2C

CH2CH3 +

HCl

Ethyl phenyl ketone

K
WJ
W K

W
O

CuO-Ag
O

2H

+ 2H 2O

500-650 C

O
CH2

+ O2

2CH 3OH

(1

CH2 +

1/2 O2

PdCl2

CH3

H 2O

(2
H

W K
K500 CO2-propanol
O
(CH3)2CHOH

Cu as Cat.
O

CH3

CH3

500 C

2-Propanol

Acetone

W7J 5

K
- -

EF
W
.(Cyanohydrine )HCN .
OH

O
C

CH3

HCN

CN

CH3

CN

Acetaldehyde cyanohydrine

O
C

CH3

CH3

HCN

OH

CN

CH3

CH3
CN

Acetone cyanohydrine

W .

WG-NH2
O

OH
NH Ar
H=G

C NH 2
NH

K
K

F

K E
O
CH 3

CH 3

NHNH 2

+
H

CH 3

NH

CH 3

Acetone Phenylhydrazene

- -

WReduction .

KNaBH4
OH
H2/Pt

O
C

CH3

CH 3

CH 3

1)NaBH 4
2)H 2 O

CH 3

CH

CH 3

CH

CH 3

OH

2-Propanol

WOxidation .

K
O

(O)

OH

- -

EF
O

Cl

W .

(2

CH 3CH 2C

(1

O
C

(4

(CH 3)2CHCCH(CH 3)2

(3

(5

CH 3CH 2CH 2 CCH 3

W .
Acetophenone
Benzylphenyl ketone
3-Pentanone

(2
(4
(6

Benzaldehyde
Benzophenone
Butanal

(1
(3
(5

W .

O
Cl

(1

O
CH 3 CH 2 CH 2 C

(2

(3

1) NaBH 4
+
2) H3O

1) NaBH 4
+
2) H3O

O
NH 2 OH

CH 3 C CH 3

(4

(5

(6

O
CH 3 C

Oxidation.

H
O

CH 3 CH 2 C

H 2 / Pt

- -

EF
. 2-Chlorocyclohexanone (2

WE1F

. Propanol
. Methyl propyl ketone

(1
(3

WE2F
CHO

CH3 CH2 CH2 C-H

(4

N-OH

CH3 -C- CH3

(4

(1

CH3 CH2 CH2 C-CH3

(6

WE3F
CH3 CH2 CH2 CH2 OH

(2

OH

CH3 CH2 C CH3

(6

- -


]<gj]<]<j<^]<]

W
W
K .

K .

W
K80

W
K

W
KOverhead Projector .
K .
W
K

- -

W8J 1
EJ COOH)

KE-OHF EC=OFK

K
W8J 2
WJ

KE8J 1FKWK
WEE8J 1FF

Formic

HCOOH

Acetum

Formic acid

Acetic acid
CH3COOH

Butyrum

CH3(CH2)2COOH

Butyric acid

KKK
K

- -

C
5

C
2

O
C
1

OH

W
CH3

CH3

CH3

CH

CH

COOH

2,3-Dimethylbutanoic acid

-Dimethylbutyric acid

WIUPAC W
eoic acid

W
Br

O
CH3

CH3

OH

CH

COOH

2-Bromopropanoic acid

Ethanoic acid
(Acetic acid)

COOH

CH3
CH3

CHCOOH
Cyclohexane

3-Methyl-2-butenoic acid

Carboxylic acid

- -

WW
W .
OH

COOH

CH3

COOH

Benzoic acid

Salicylic acid

COOH

P-Toluic acid

.
W

COOH

COOH

COOH

COOH
COOH

CH2
COOH

CH2

(CH2)4

CH2

COOH
COOH

COOH

COOH

Oxalic acid Malonic acid

Succinic acid Adipic acid

Phthalic acid

Fatty acids .
2612

CH 3 (CH 2)14 COOH

CH3 (CH 2)16 COOH

Palmitic acid

Stearic acid

- -

W8J 3

KO100L46Z

KO78L46Z

HCOOH

Formic acid

C2H5OH

Ethanol

O
R

EF
W8J 4

H2O

H3O + Cl
HCl

K
_

RCOOH

+ H2 O

RCOO

- -

+ H3 O

K
W
_

O
R

O
C

W
WElectron-withdrawing group .

....., -COOH , -SO3H , -CN , -NO2 , Br , Cl ,F

Benzoic acid p-Nitro Benzoic acid
KPara -NO2

:Electron-donating group .

-OH , -NH2 , -OCH3 , -CH3

KJ CH3

EInductetive effectF
EpKaF

WEChlorobutyricF

- -

CH3CHCH 2COOH

CH3CH2CHCOOH

CH 3CH 2CH 2COOH

PKa = 4.82

CH2CH2CH2COOH
PKa = 4.52

PKa = 4.05

PKa = 2.85

Z1

Cl

Cl

Cl

92

Ka

W pKa

Ka

_
+
[ RCOO ] [ H ]
[ RCOOH ]

_ log Ka = pKa
KpKaKa

Ka
pKa

3.74

4.47

4.85

pKa

Ka

1.77*10-4
1.76*10-5
1.43*10-5

HCOOH
CH3COOH
CH3CH2COOH

W8J 5

- -

W .
O
RCH 2

OH

OR

H2Cr 2O7

RCOOH

+3

Cr

( )

W .

.(Ar)R-CN

K
R-X

_
CN

RCN

K
+

RCN

H3O

+
RCOOH + NH 4

W .

R
KMnO4 ,

COOH

C2H5
KMnO4 ,

Benzoic acid

Ethyl benzene

- -

W 8J 6

K
K

W .
_

CH3COOH + NaOH

CH3COO Na + H 2O

Acetic acid

Sodium acetate
_ +

Ph COO Na + H 2O

Ph COOH + NaOH

Sodium benzoate
Benzoic acid

(Ar) R COOH + NaHCO 3

(Ar) R COO Na + H 2O + CO2

K
RCON

W .

RCOORRCOCl
O

K
R-C-O-C-R
W8- 7
E-OHF
NH2Cl-RCOO-J OR

W
- -

CH3 C

Cl

Acetyl chloride

CH3 C

OC2H5

CH3

Ethyl acetate

NH2

Benzamide

O
C

O
O
O

CH3 C

O
C

C
_

CH3

Acetanhydride

O Na Sodium acetate

O
C

OR

O
R

NH2

O
O

C
_

R
+

O M

7J 8J 1
:Acid halides W
-yl halide - ic acid

O
CH3

O
CH3

OH

Acetic acid

Cl

Acetyl chloride

:Esters W
-ate -ic acid

WKEF
- -

O
CH3

OH

CH3

Acetic acid

OC2H5

Ethyl acetate
WAmidesW

WKamideJ oicAcid
O
CH3 CH2

CH3 CH2

OH

NH2

Propanamide

Propanoic acid

WAcid anhydridesW

.anhydrideacid
O
O
C O C

O
C O OH

Benzoic acid

Benzoic anhydride

:Acid saltsW

O
CH3

O
OH

CH3

Acetic acid

O NH 4

Ammonium acetate

- -

W7J 8J 2

K
EF

K
O

..

R-C-NH 2

_
O

+
R-C = NH 2

,
R

.. +

NH2

- -

W7J 8J 3
K
O
R

Cl

SOCl 2
in Benzene
O

O
R

O
R

SH 2SO 4

Acid anhydride

OH

Acid
NH 3

O
R

ROH

OR

Ester

NaOH

NH 2

O Na

Acid salt

Amide

- -

EF

W K

1)

2)

OH

CH 3 CH CH C

CO 2H
OH

OH NH 2
NH 2

3)

4)

CH3 CH2 CH 2 C O NH 4
O

5)

O
O

CH 3

6)

7)

CH 3 CH 2 C

a) 2,3-dibromopentanoic acid.
b) Methyl benzoate.
c) Methyl formamide.
d) m-nitrobenzoyl chloride.
e) Potassium formate.
f) N,N-diethylpropanamide.
g) Benzoic formic anhydride.
h) Ethyl 2-aminopropanoate.

CH 3 CH 2 C

OCH 3
CH 3

CH 3

Cl

8)

CH3 CH 2 CH 2 C

NH 2

W K

K
K

K
- -

K
K

W K
+

1)

2)

CN

CH3

CH 2H5
O

3)

CH3CH2 C

OH

SOCl 2
Benzene

4)

CH3 C

OH

5)

2CH3 C CH3

H 2O / H

H2SO4

- -

KMnO 4

?
?

EF

WE1F

2) 4-Amino-2-hydroxy benzoic acid.

4) Methyl propanoate.
5) Acetic benzoic anhydride.
7) Propanoyl chloride.

WE2F
O
H-C-NHCH 3

(3

CH 3 -CH2-CH-CH-COOH

(1

Br Br

O _
+
H-C-O K

(5

-C-O-C-H

(7

WE3F

H-C-OH

+ H-C-O

KE H F
O
CH3-C-OH

+ CH3-C-O

" "

??E
CH3F
KEH+F
- -

K

K

WE4F

O
CH3-C-O C 2H5 (4

HOOC

COOH

(2

- -


]<gj]<]<j<^]<]

W
W
K .

K .
K .

W
K90

W
KOverhead Projector .
K .

W
K

- -

W8-1
EF
KEFEF

KEF

KRR3N , R2NH , RNH2

EF

K
W8-2
W8-2-1

W
3O

2O

1O

K
K

(C2H5)3N

(CH3)2NH

Triethylamine

Dimethylamine

Pyridine

CH3NH2

Methylamine

NHCH3

N-Methyl aniline

NH2

Aniline

- -

W8-2-2

WW

amine
W
CH3

CH3

CH3NH2

CH3

Methylamine (1)

NH

CH3

Dimethylamine (2)

CH3

CH3
o

Trimethylamine (3)

CH3

CH3CH2CHNH2
o

sec-Butylamine (1)

CH3CH2

CH3
o

Ethydimethylamine (3)

W
NH2

Cl

NH(CH3)

Cl

NH2
NO2

Cl
O-Nitroaniline

2,4,6-Trichloroaniline

N-Methylaniline

NH2

CH3
p-Toluidine

KP- ToluidineToluidineAminotoluene

- -

N
N

H
Pyrrolidine

H
Pipyridine

N
N
Pyridine

Quinoline

Pyrrole

WW

IUPAC

Amino

W
CH3

CH3 CH CH2 CH

CH3 CH2 CH CH2 CH CH3

CH3

NH2

NH2
5-Methyl -3-aminohexane

2-Amino-4-phenylpentane

H2N CH2 CH2 CH2 COOH

CH3 CH

NH

CH2 CH3

CH2CH2CH2CH3

4-Aminobutanoic acid

2-(N-Ethyl amino)hexane
COOH

NH2
P-Aminobenzoic acid

WW

EAmmoniumFEAmineF

(Anilinium)EAnilineF

- -

CH3
+

+ _
NH3 Br
_

CH3-N-CH 3 I
CH3

Anilinium bromide

Tetramethylammonium

W8J 3

(C2H5)2NH, (CH3)3N, (CH3)2NH, WEF

J FCH3NH2

E11F E
K

K
E F

KE8-1F
KE8-1F

- 42

44

Propane

CH3CH2CH2

17

45

Ethylamine

CH3CH2NH2

7.5

45

Dimethylamine

CH3NHCH 3

78

46

Ethyl alcohol

CH3CH2OH

100.5

46

Formic acid

HCOOH

KK
- -

W8- 4

K
_

[ RNH 3 ] X
RNH 2 + HX

. NH2

NH2
_

NH2

NH2

Resonance structures of aniline

EF

KSO3HNO2

OCH3

NH2

NH2

>

NH2

>
NO2

OCH 3

- -

KKb

_
R NH 3 + OH
+

R NH 2 + H2O

Alkylammonium ion

Amine

Kb =

[ R _ NH3] [ OH ]

[ R _ NH2 ]

KK Kb

pKb Kb
WpKb
NH2

_ 10

CH3NH2

NH3

K b = 1.8 * 10

pK b= 9.38

pK b= 4.74

(CH3)3 N

pK b= 4.26
_
10

K b = 5.5 * 10

_4

_4

_5

K b = 4.2 * 10

(CH3)2 NH

K b= 5.1 * 10

K b= 4.4 * 10

pK b= 3.36

pK b= 3.29

- -

W8-5
W
W
W

W J
H3N

+ R X

OH

R NH 3 X

R NH 2

o
Primaryamine 1

Alkyl halide

W J

CH 3CH 2NH 2

1) CH3Cl
2) OH

CH 3CH 2NH
CH 3

(1)

(2)

+ H2O + X

K K

LIAIH4

K
CH3 NO2

H2 / Pt

CH3 NH2

Nitromethane

NO2

Fe / HCl

Methylamine
+

NH3Cl

Na2CO3

NH2

K K

LIAIH4

- -

CH3CH2 C

H2 / Pd

or

LiAlH4 / Ether

H2 / Pd

CH3 CH2 CH2 NH2

CH2 NH2

Hofman degradationW
NaOBr

WEF
O
CH 3(CH 2)4 C NH 2 + Br2

4NaOH

CH 3(CH 2)4 NH2 + By Products

H2O

K J

KNitroalkanes J
J
NitrobenzenePhenylamine
K

- -

W8- 6
W
WHCl J
CH3 CH2 NH2 + HCl

_
+
CH3 CH2 NH3 Cl

(CH3)3 N + HCl

_
+
(CH3)3 NHCl

WNitrous acid J
J
J F NaNO2

Diazonium saltsEO

K
K
O

Ph NH2 + HNO2

0-5 C

Ph N2
Diazonium ion

F J

ENaNO2HCl

KEFNitrosoamine

CH 3 (CH 2)4 CH 2 NH 2
o

(1) amine

HNO2

- -

+ N2

CH3(CH2) NH

N=O

HNO2

CH3 CH2-N-CH 2 CH3 + H2O

2 amine

+ H2 O

N-Nitrosodiethylamine

HNO2

No reactions.
(CH3 CH2)3 N
W J

W K

NH2

NH2
Br2 / H2O

Br

Br
Br

Aniline

2,4,6-Tribromoaniline

K
NHCOCH3

NH2

Br2

(CH3CO)2O

H2O / H

Br

Br

Aniline

Acetanilide

NH2

NHCOCH3

p-Bromoacetanilide

p-Bromoaniline

W K

N+H3

p- Nitroaniline

W

- -

NH2

NHCOCH 3

NHCOCH 3

+
H2O/H

(CH3CO)2O

NH2

H2SO4/15C
H2 O

NO2

NO2

P-Nitroacetanilide

P-Nitroaniline

W K

K
+

NH2

NH3

NH3HSO4
O

180-200 C

H2SO4

Aniline

Anilinium hydrogen
sulphate

SO3
Sulphanilic acid

WJ

H2N-(CH2)6-H2N"1,6-hexamethylenediamine"
hexamethylenediamine

C6H12N4Wurotropin

EformaldehydeFKo
oEFEF

octogenhexogen
C6H5-NH2
K

aniline

- -

EhydroquinoneF

KEF

- -

EF

W K

2) CH3 CH2 CH CH3

1) CH3 CH2 N(CH3)2

NH2

3)

4) CH3 CH CH2 CH2CH2

_
+
CH3 CH2 N(CH3)3I

5)

NH2

Br

6)

NH2

CH CH2 CH2
NH2

OH

Br

W K

1) Cyclopentylamine .
3) 1,6-Hexamethylendiamine .
5) N,N-Dimethylamine .

2) B-phenylethylamine .
4) Benzylamine .
6)tetra-n-Butylammonium
iodide .

7) P-Aminobenzoic acid .

K K
1)

CH3 CH2 CH NH2

CH3

3)

2)

+
(CH3)3 NHNO3

4)

(CH3CH2) C NH2

NH
_

5)

+
N(CH3)2 Cl

7)

N(CH3)2

6)
8)

NCH3

(CH3)2 CH N (CH3)3 Br

K K
W K
O2 N

NH 2

CH 3O

- -

NH 2

NH 2

(A

NH3
a)

(CH3)2 NH

2)

CH3-C-NH 2

(B

OH

Br

?
NH2

NO2
H2 / Pt

CH3CH2CN

e) CH3NH2 +

CH3 NH3Cl

HNO2

NH 2

(CH 3CH2)2 N CH 3

4NaOH
H2O

d) CH3CH2 C NH2 + Br2

g)

(CH3)3 N

1) CH3Cl

(CH 3CH 2)2 NH

b)

f)

W K

Br

c)

Br

NH 2
Br

Br

h)

NH2 + CH3Cl

- -

EF
1) Ethyl dimethyl amine .
5) O- bromo aniline .

WE1F

4) 1-Amino-4-bromo pentane .

WEF
CH 2NH 2

(4

NH 2
+

KE3
KE6

(1

(CH 3CH 2CH 2CH2)4 N I

(6

WEF
KE2
KE4

WEF

P-methoxy aniline > Aniline > P-Nitro aniline .

WEF
CH3CH 2CH2 NH2 (c

K (f

(CH 3CH 2)2 N CH 3

HCl

(a
(e

- -

W
W K
K

WK K

K K
K K

K K

WW
1.Fessenden, Ralph J.and Fessenden, Joan S. Organic Chemistry ,2nd ed, PWS, Boston
1982.

- -

J J

J J

J J

J J

J J

J J

J J
J

J J

J J

J J

J J

J J
J

J
J

J
J

J
J

J
J

J J

J J

J J

J
J

EF
GOTEVOT appreciates the financial support provided by BAE SYSTEMS