KEY CONCEPTS

ALCOHOL . .
'

methods of preparation

H20/He
CH2=CH2

0
CH2=CH2 BH3'H202/0H

(Ac0)2 Hg/H20/NaBH.t
CH2=CH2

aq. NaOH
CH3CHrCl
63
CH3MgBr/H30
H-C-H
II
0
63
Hi/Pd or LiA1RJH
CHrCH=O
reduction
63
LiA1RJH
CHrC-Cl reduction
II
0 63
LiAlllt/H
CH3-C-OCH2CH3 - reduction
- II
0
NaOH
CH3-C-OCH2CH3

H30e
CH3-C-OCH2CH3 reversible reaction
II
0
NaN02+HCl
CH3CH:rNH2 orHN02

dil. H2S04
CH3CH:z-O-CH2CH3 A
fJ Chemical reactions of alcohol
PCl3 or PCl5 or SOCli ::-- R--Cl

Lucas reagent -~ R--C

(H--Cl + ZnCli)

H NH 2/AliOia R- NH2
(-H2O)
-
H-0-NOz/l 00°c ; R-O-NO2 (Alkyl nitrate)
(- H2O)
H2SOJ100°C ; R-HSO4 (Alkyl hydrogen sulphate)
(-H2O)

0 0
. llttme II
R'--C-0 ; R'--C-OR
(-H2O) -

0 .
II 0 ..
CH~-Cl II
: CH3--C-OR'
(-HCl)

R-0-H (i) Na (ii) R'-X

- Williamson synthesis
. R-0-R'
Alcohol
. CH2=C=O
; CH3-C-OR
.. Ketene II .
0
HN=C=O ... H N-C-OR
Isocyanic acid
. 2
II
0
.
R'MgX
..... R'-H
Grignard reagent

0 ..
II
Ph--C--Cl _,._
Schotten-Baumann reaction

HI +redP
.... R-H
reduction

CH2Nz/~
....
H2SOJ170°C
.... Alkene

H2SOJ140°C .- R-0-R
Oxidation [O]
,... aldehyde/ketone - - ~ Carboxylic acid
 ation of ethanol by fermentation
Crystalisation
cane sugar Sucrose molasses _
(1) .
hydroJyliJ
Zymase
invert sugar EtOH

30% surcose (30-32% Invert sugar)

in __. Starch Diastase

(2) gra HOH , maltose - Ma11asc
g1ucose ZYDlae EtOH

ETHER

l[General methods of_p~e~~~~tion

J
A 20

(2) CiHsl ~- CzHsONa

Williamson ether synthesis

(3) ~HsOH _ _;___· C_·o_'n_c.-:--H..;;2s_6_4""'.',l:-4_0"C_· --~r, CzH,--0--GH,

, Williamson continuol,IS ether process
i-' r - },t>-. -- -
. I

,... I"' • \ J -, ;

. . -. --~ci-c H~HrCHJ
(4) ~Hs-Mg-Br
. Lower ether

(5) CiHsOH 180:-200"0:

II Chemical reactions

BF3 _ _.. CH3CH2'->0

- _
....__ CH3CHV .. -+ Bf3

CH3CH2 - -CH2CH3 -
RMgX -R-Mg-X
Grignard reagent ·. . t
CH3CH:rQ--CH2CIJ3 ·_: _' .
j
.}
•

EB- - - -·· e --.. . ,

I--HF::.::....---+[CHi;H~JI-CH2CH3) f
- EB · . e
1--....H::.::.;C;;;.l~-•[CH3CHz-2H-CH2CH3) Cl
·- ~.,:.;HI:.;;.~:'·/.:.;.HB=r~_,.cii3CH2I
;:, + CH3CH20H (Ziesel ~eaction)
(Cold and cone.)

HI or HBr 2 CH3CH2I + H20

(Hot~-con~.)

BCh 3 GH3CHrCl + (CH3CHzhB0J

t • ""':"":'-- ...- . '; " -.- ,

PCI, I A . _2 CH3CHrCl + P~l3 _

~- .... ... -- .
<1tti '. • •'· ::.~- ._-{ j'-_..... .
-.
' ·. -..
CH3COCI /AICh .. 'l CH3CH;tl +CH3i--OCH2CH3
. . 0

~~3_C H~H2CH3
t' - 0
L-,:d:il:.::,.H~2S;;,:O~•'/;.;A__-+ 2 CH3CHz-()H

- --..CH3iH~H-CH3 (a,a'-dich1oro ether)

1--.:;;Cl;:..;2'.;:dadc;;;;;.
Cl . Cl

L-.:C~hL:.l.:::slin::::1::12i.;.;t_
- -+ CCh-CCh--0-CClrCCh (Per chloro ether)
~ I reactions

(1) air
Et-O-CH(CH3)-O-0-H

(2) PC
~H5Cl + POC13

(Hot & Cone.) 2HI

(3) 2C2Hsl +H2O
Determination of alkoxy
groups by Ziesel's method

(Cold & Oil) HI

(4) C2Hsl + ~HsOH

Ch,20°C
(5) a, a'- Diehloro ether
dark, /l.

Ch (C2ct5) 2Q penta ehloro etl

(6)
hv, sunlight
..
CH3CH2 --Q-
Diethyl e Cone. H2SO4
(7) Oxonium salt

BF3 (Et)20-tBF3
(8)

co, 1so c 0
Et-COOEt
(9)
H2O & BF3, 500 attn

CH3COG1 CH3COOC2Hs
(10)
anhy ZnCh

(11) AhO3 CH2=CH2

380°C

(12) . dil. H2SO4 EtOH

 I

ufBr
,. ., Synthesis of phenol & chemical reactions

@ Na,.__....:.:;~--t
Na or
NaOH
NaHCOi
. - -
. -
Br2
Halogenatton
c= H,O

~~or.
...,, 'r,
iQHr +Qj_HH_Br
rgT

I @NH2 ...
· -NHi/AhOi/6
-----t
(-H20) .
Nitration

I 'ry -~Zn---t
II
I I Cl
Reduction

~Q + PhiPO• --..:..=:~----1
(SJ PCls
11, Sulphonation
(Major)
I
HO--@._ ;@-OH CH1-CH3 I H2SO,
· CH~-CH3 · (-H20)
(Bis-Phenol- A) - OH OH

Ii' CHJCI/ AICh @rCH,

Friedel - Craft ~+
ii reaction CH,
I' (Phenolphthalein) OH OH
i @rCOCH,,
@-[ Jo' +--=@-c_t:_,
CH~-CI / AICh
-1
Scholten Baumann Friedel - Craft ~+
OH reaction , reaction COCH,

fl
0--C-CH,
OH

fl
CH,...C-CI
Phenol CHiCI / KOH (ale.) ©rCHO +
Reimer-Tiemann
(-HCI)
reaction
CHO
OH OH

u
(Cyclohexanol)
CCl4 /KOH
Reimer-Tiemann
reaction
©JcooH
+

COOH

OH
FeCI,
· Voile! colour - - - N 0111
--'.,al--_
-l (i) HCN + HCI / AICh
©rCHO +
(ii) H3Oe
' t Gattermann Reaction CHO
! (Quinol) -~H -__,;K,S,0;..;...1;.../K_O_H_ _ _ (i) NaOH
~o
OCOONa OH
I Elb's pursulphate
t--';(i,;-,i)~C..:Oi:../~14.:.;;0,..::°C:.___ /2_ H ramnged COON•
- oxidation
OH Kolbe-schmidt
reaction
l8J
0 l8J
OH
H+OH
KMnO,/Iie Liebermann nitroso test
oxidation NaNO2 + H2S04 H,so, Green~ Red
H--t-,-OH
COOH
NaoH.J,
N=O

r£
(mesotartaric acid) Blue

¢--au-· &;...:ligh:....t_ _1
Lederer Mannase

CH~
OH

·~+~".:":;::
0
CH,OH