- -
-.
PROF i
So B
MUSTAFA.
MUSTAFA
#
SIR
AICOHOL PHENOL AND STHERS
Final Goops:
AcohOl · R-0H
Phenol Ar-oH I co
Ethers: R-O-R
(Ot) containing
cohols are
hydroxy zing
to cliphatic
compounds attached
eg: CHs-CHe-CHz-OH
(on) containing
henols
↑ are hydroxy
is attached
componds where on group
to the benzene ring.
[0]-on with Ohygen
Ethers are compared
arom attached to alkyl or
any
side.
group on either
9.
CaH5-o-C2Hs
E+5
[]
- o -
CLASSIFICATION OF ACCOMOUS
the on alcohols
Depending of group,
on no are
as
classified
on x city-on
hydric:
one
Mono
Dihydric: Two
three
ONzx
on
CHe-CMe
ove
Trihydric: IS
CH2-H-ceis
the name of carbon
epending
on
D
as
Alcohols are classified
1 alcohol: CH5-CHe-OH
a alcohol: Ciz-cH-C3
6H
3 alcohos: CH3
&
Ctz-c-OH
cy MUSTAFASIR
#
S OME OTHER CLASSIFICATIONS
attached to carbon
ic alcohol:
On
#
next to c = c
9 :CHz=CH-CHc-OH
enzylic
3) Alcohol: Of attached to caben bonded
--
benzone
to wing.
&cHe-on
NOMENCLATURE
A) ALCOHOLS
Common: Alkyl alcohol
UPAC:
*
Alkanol
LOOK
* INTO LECTURES FOR
ETTER
* UNDERSTANDING
B) FOLS;
⑳ #ERS
Ethers
Common Name:
-
Alkyl
-
IUPAC Name, lkoxy
A Alkane
--
MUSTAFA
#
SIR
METHODS OF PREPARATION (ALCONOLS
ACKYL HALIDES
#
FROM
->R 6H + kx
1 x
k0H
-
+
-
+KB2
CM5 Br +k0U -> CaN5OH
alcobo
sebromide Exyl
ALKENES
&
FROM
c
+HC1 ->(Hz-CHg-cl
CHa=CHa
I
2 there
Euylchioside
-C MR
Cus-CH=CHe +Hc1
-
->CUs--cts
2 -
chic propane
Note: MR: Malkonikoffs Rule
-
NUSTAFA
#
SIR
&
Reduction of Carbonyl compounds
a) om hyde
CHg--H L iA11y
->CH,-cHa-on
NgO
t
Athanal Ethano
3Ketonesits OH NOTE 8
-
cus-ciaon LIAlHy is
as a
acting
reducing
Propan-2-01
Ace lone which
agent,
can provide
2) From Anids? Ht to the
reaction
O
Li A lHY
Cur-i-on->(15-CHe-OH
As Ot
Acetic Acid Ithaw 1
d) From Essel
cric-o-cts
acetate
the city-ci,on+cou
meltyl Erraw ( methaw
NUSTAFA
#
-> IR
Addition of Grigned Reagent
Fodehyde s
(cis-gior
0 H
Br
O in Cky-cir-cny+Ng ~
citg-c-i+
geare
on
OM
Exuanal (
scomide propan-2 -o
<20 Alcohol)
From Kone; & It3
-(Custongn F,
I
aks--ches+ckbNgBr Cts-c-on
A
ce lone cits
2 Metal propante on -
↑ 3 Alcoholi
Mox: Fomaldelyde+UR->(alcoho
All occur
ordemde
+44-2"alcohol
9R -> Salcoh
becomes +
REPARATION
↑
OF PHENOLS
from chlorobenzene (Dow's Process):
#)
-
·If
· Na
Corres [].[
char S o diver Phenol
benzene ↑henoxide
B) from Comene (Iso propyl Benzene
CHs-CH-CH3 cks
-
300 -
H ·H
& O
↓i l
N ↑I
02 - -
CHz-c-CH,
+
423K HCI ↑
Ace to ne
propyl C mene
I
so
hydro peroxide henol
↑
Benzene
A cd
C) From
-
B
enzene
-
sulphaic -
OH
· Na
SO3H 503 Na &
& & &
NaOH Nao H di(
- -
-
HCS
he not
↑
enzene
* So dium So diam
B
enzene
SIronic Phenoxide
Acid S ulphonale
too Aniline -
d)
m
-.
0H
Necl
#H2 &
&
&
NaNOZ H20 F
N2
+
HNO2
↑ - -
#Cl
B
enzene phenol
Aniline
diazonium
chlovide
NUSTAFA
#
SIR
PHYSICAL ROPERTIES
*
As are moleculal Forces
-
-> Alcohol and phenol are polae in nature
Y
If
held
together by Hydrogen Bonding
lower alcohols are
Basicalate:
colorless, toxic
alcohol
4) Boing point:
The boiling pt of
ncrease
↑
with molecular masses
CHEMICAL PROPERTIES
A) Reaction with base -
mmm
phenols less acidic compat
or:
↑ are
very
to alcohol; Hence phenols cannot be
reached with
Hancos out reacts with
#a 0 H
No reaction
Ar-oH +NaHCOs ->
An-oH+Naot-> Ar-orNa+ HcO
B) ht rPols:
↑henol+Ferric -> Ferric ↑ Hc)
Chloride phenoxide
c deep color)
Ar-oH+FeCs
->(Ar-0,-Fe +HC)
2) EriFintion:
O
O
R-OH + OH-C-R -
T
-
-
&- i-o-R+HzO
Acid [ESter]
Icohol
*
O
O
11
0-- 2H,
CH5-0-c-CHy
= >
H + H
: CHz
0 - -
-
Methanol
Acenfeid meterl
pare
ace
O O O
3)R-0H+ R-C- 0-i- RER-c- O-R
Ester
#
1040 1 Anhydride +
R-COOU
Acid
O O
2
CHz-OH +CH,c-0-c-CH3 CHj-c-0-CHE
O
D
=>
( mettr
alcolo ( Acenhydride menace race
+
CHgCOOU
Acetic Acid
O
2
R - 0x + c- -
x ->
R - a-- R +
HC
1cohol
# Acyl assee
chinde
O
O
c-i-CH3 -> c15-0--c + HC,
e. :CNgOH
+
mettel
meney ( Acetyl
alcohol chloside accrace
NUSTAFA
#
SIR
cetyl
A Derivative e
-..
100 H COOH
O
& &
-
OH O O
o--CH3
ctc-o-CHs
-
-
t
CHCOOH
#
Acetic Anhydride
Acetic
-> alicylic cety (
A
Acid
Acid
Acid Salicylic
& As pizin)
Aspirin known Generic dedicine.
Note: is well
Reactions of Alcohol
(Breaking of C-0 bond)
#
Action of Hydrogen halides (Ax)
R- OH + HX -> R- x +
HeO
encle
=.:(H50H +HCI - 'HyC1 + H2O
Ethanol EHt
chicride
or:
↓ Order of reactivity HITHB>HC,
* Reaction with phosphorous halides
cls
↑ 1 -
C 1
↑(Ig R- cl
R -
0 H
SOCI2 R -
cl
NUSTAFA
#
SIR
Dehydration of a
hol?
12 B1 Bl CHg-CH-CH=CH2
=>
a KOHf But 1 -ene
2
H5-CHe-CH-CH3
-
call
die 12 ⑧
CH-CH
CHz-CH= 3
But z
-
-
ene
<majo)
Note: Major alkene can be obtained
using "SaytzeR* Rule"
O XIDATION OF ALCOHOLS
Aldehyde > Carboxy1:(
oxidatice
1alcohol--
Acid
oxidation
2 alcohol ->
Kecome
9.
, CMsco
City-Con Pcc
Acetaldelyde
Ettey I
alcohol
CHz-CH-C13 -
COS CH3
-
"-cs
⑥H 1MnOu Ace tone
1 copan-2-01
Chlow Chromate)
Note
-
PCC (pyridinium
is a
reagent used as
oxidising agent
acid.
which stop conversion of aldelyde to
NUSTAFA
#
SIR
R
FACTION OF PHENOLS
A) Halogenation of mo
Off
& If
& &
Be Br
H20 * -
+ 3BU2 3HBr
-> ->
"Ba
2. 4.6 Tribromo
Pheno
& If & If & If
& & &
Br
CS2 ~
+ Bue ->
+ + 2H Ba
0-BCom o Bo
phenol ↑- B20m8
phenol
B) Amation of Anou B
& If & If
& If
& & &
NOZ
->
t H NOs - # 2H20
↑
LOH -
NO2]
ix02
·-Nileo
↑he not
p-Nicro
& If Phenol
&
& If
Conc
&
3HNOs
= NOz NO2
He sou
↑
LON -
NOL] 3H20
↓
Oz
↑
2) 416
Trixito phenol
② Sonation of Phenol e
on
&
SO3I
293K*
& If
&
HesOn
· -phenol
OH-SOSH 37,k & If
-
opphonic
⑱
& Acid.
Sos'
p
-
phenolsulfonic Acid
④ Enmer-Fann Ration
9 *I a ·
forcanon
cno
CHO
↑eco
-
->
2 -
Hydro all
Benzaldeyde
asicyal day
-> de
#
KABE RENTION:
& If & If
& & & If
NaoH ~ COONC &
Cool
->
a
-
-
CO2/398K
so dirm
salicylate 2-Hud20 x
T
enzoic Acid
B
&Salicyclic Acid)
T
NUSTAFA
#
SIR
&
OXIPATION of HENOL
↑
9
i 8
H
as ,
P-
Benzoquinone
&
Catalytic Hydrogenation of phenol
cons
9
i
she
-
henol
↑ 9 clohexanol
& -FAo):
Reduction
& If
&
an
1x
*
->
+ zn0
Benzene
henol
↑
NUSTAFA
#
SIR
&THERS
Method of Penn
-
④ Dehuation of at
ho
He sou
2 cHyCHeON->
4 13K
CHj-CHz-0-CH, -CHs
&full alcohol icstyl[thee
*
Ethanol it carried
ote: Dehydration of
↑
instead of Ether
out an husk gives a there
⑬ Williamson Sytmsis:
-
Do 1-0-1+Hax
1 -
x + Na-0-k ->
Skee
S odiuce Ether
lkyl
A
Alkoxide
halide
NaBr
CH-O-CeHs
-
:
&
CettsBr+Na-o-CHs
&thox y
Et 1
600 mide 2 Mane
ole I
-
#EMICAL PROPERTIES OF ETHER.
⑰ Formation of Provide: o
- 0 -
H
C.Hg-CHe-O-CHjCUs tOc
->CAs-CH-o-GUs
Peroxide of
Diettyl Ether
pic/tys [thee
NOne i
-
with nor Heson:
⑬ Reaction
21 -
01
H- on-
R- o-R +
*Icohol
& thes
-o-p'
R + H -
On -> R-OH + R'ou
alconer
ecHz 0 cxz H +
(Hj-Oi
-
+
cHz-0H
-
- ox ->
Dimeter l meter (
2 ther
methyl
alcohol alcohol
MUSTAFA
#
SIR
Reaction with PC15
R
-
o - R +
P(15 -
R -
c1 + x -
c1 + POCs
e:CH5O-C13 -C1 +POCIs
Dimetry I PC1y ->2(Hj
+
2 then metly
chloride
Reaction with hot HI
HX -> R-OH + R x
⑭ O-R+
-
1 -
alcohol Alky
2 ther
halide
CHg-O-CH3 +HI -> cHg-OH +CHs- I
meter/ metly/
methONY alcohol bromide
methane
on:
#
Order ofReactivity
& I> HBr>HC/
8.
CHg
20] + H+
398K
- [ + CMsF
Anisole Phenol i
met
#
LECTROPHILK SUBSTITUTION
⑰ Halogenation:
got
to
Loos
OCH3
I
So on
p-Bromo
sole
Br o-Bromo
Amisole
An:
want on:
⑬
Fidels
Coto
a
[of Timor &
cl
Methoxy
Cnetin
inter
dobois
can
cast-> Coats so
O
Acetyl
chiovide d
Methoxy
0
2-
=
cikg cetophenone
A
4 -Methoxf
cetophenone
A
* TION;
give city
XOZ
Logoc
~
CETOs IS,
on
↓Oz
9 - Niko
a-Hithole
Anisole
M YOU
#
HUSTAFA SIR
ALL THE BEST
