Phenols Aromatic

Phenol is the specific name its used

hydwxybenzene
forbenzene and
for the derivatives of hydwxy also

OH OH
OH
e
g 4 IT d
Lot Cling
Moz
3 Bromophenol h methylphenol 4 nitrophenol
or or
m Bromophenol p methylphenol p nitrophenof

i
6
3
5 4
2 Naphthol
1 Naphthol
B Noraphthol
or
a Naphthol

IUPAC Names Recap

OH OH OH OH
d Utz OH
da k
Lot Loko led
2 Methylphenol
o cresol
1,2Benzenediol 1,3 Benzenediot IH
catechol resorcinol 1,4Benzenediot
Hydroquinone
OH
1I
02N
6 12 Moz
S
s
ay
Lik
214,6 Trinitrophenol
Picricacid
PreparationofPhend
Lab preparation Hydrolysis of arenediazonium salt

EN
E me
FI É on

E de
15
de
Mechanism

EJMie.fm gni oJ rn
ig
ii o

Tf Tautomerise
Ph NII OH

I let
Ph nice or Ph I n éÉ Ph Mini
8g
Relativelystable
Benddiazoniford

X R NEN É É É ROH
 Industrial Preparation
t.is cess o
Effie
12 µg
phenol
addition eliminationmechanism

2 Alkali fusion of sodiumbenzenesulfonate

et so
soimat.gg ffjoNat
Phenol
e
g SOINat OH
350C
I HU
us 1
cuz

3 from Ceemene Hydroperoxide Most

ofthe worldwide production of phenol
is based on this method
Utz
Ii
i
Clement m I
AimeeHydroperonide
queue Uts Ue Uts

f µ

ae.info ph
I shift
Utz
Cee c o Ph
t's
aesfj.to ph cnsqo uytPh oH
 Acidic character
of phenol
stronger acids than alcohols due to resonance stabilized phenoxide ion

PKa
i s
EIS j FILET
1.0 Phenoxideion
ka 16

no
Ej L ka 15
S
pKa

Presence the acidity

EEG 9
of ELSE 4 the acidity

OH
es I
I 9 1
Mozem Moz Moz
PKa 7.23 8.35 7.14 4.01 1.02

OH 12 OH
metajarasouno
IET Ms
I
Ie G1 Hyperon
Pkg 10.28 10.08 10.19

OH
a
ortho meta para
egg I
U 1
a
pKa 8.48 9.02 9.38
Phenols react with
Nda while alcohols dont to a significantextent

0 Nat
t NaOH TT Hao
weakeracid
stronger weaker
acid
stronger
Bare pKa 16
bare
pKa 10 so e

OH t NaOH Mio Nat t HD

weakeracid weaker stronger strongeracid
pKa218 Bare LEE pka216

The fact that p sdissIeinag.N H while most a n't

allows us to distinguish a separate alcohols fromphenols
strongeracid
Most phenols however are not soluble in aq Nais but R H_
are solute Thus Naldo provides a method for distinguishing
separating most phenols from carboxylic acids

Nando
RCOOH soluble I
Ph OH No Rin
NOL NaHLOs
soluble
INOz
 2 Nitrophenol is a yellow crystalline solid

mp 46 C
Sinks in a slowlymixes with water
freely soluble in Css MOH
Very soluble in alcohol ether acetone Cl
In water 2 Ight at 20 C
Other reactions 0
o dR
rei E r E I
A noon
Ph 0 11

E
III r E
o R
a Bees
2 Williamson ether synthesis

k
eons o r inax
SO R
Nuc

e
g d
OH
name
gNat
III
TDI ploy
ON
Na
I Sµ2
Utz Ctl Uts

3 Cleavage
ofalkylarylethers 5
H
Snl
Ph OH R I
F Ph R t
p R a

let y spy2
dependingon R
e
g Ctl

Ph o
II Ph Ph OH IEGt3
J CH

Cee
in
g
z SNI
z
Cee

OH OH
Br
4 d Br
H2O
Br

Eoin
Br
 I
Major
II
1
Moz
lconc.ie
25 C
TEc 9
100 C

Magnani
I c

lessBP higher BII

o nitrophenol a p nitrophenol can be separated by
s_mLledisH_o

More volatile
I
Less volatile
sH
due to due to
intramolecular intermolecular
H bonding H bonding
d
steam volatile

1 With cone tenors phenol is converted to 2,4 6 trinitrophenol

Picricacid The yield
of rxn product is poor
PH Oz
IN
age
oxidojegelear picnic acid

Moz
pKa 1.04

owadays picric acid is prepared

by treating phenol first with
cone HEO which converts it to
P ul c acid and then with conc tenors to get picric
acid

OH
 OH
ie
I ego i
reOz

action
koplhebzeoer.de P_nde ion is even more simple to Segar than

ii at
E
OH
k Coon

Salicylicacid
G Claisen Rearrangement Heating
allylphenyl ether to200C
intramolecular reaction to generate
ellects an
o
allylphenol
a

a En e
When the ortho position is substituted rearomatization can't take
place

ii cope OH

I i
re

E EE
7 fries Rearrangement
a
01k61g OH

EI Ius Esta Kouri

Phenolesters

RC O
acyliamion
Reimer Tiemann Reaction

l
formylatio s

i Ei c

Eu EI
ma

fig
in
ca

Carboxylation

on
Eog Finals f1 Eiji
Coote Major

Reaction with active metals

ma
III team
0 Reaction with neutral fell
Phenols generate colours like violet red green or white appearance

Even salicylic acid with a phenolic group gives violet colour

on
Is violet colour

00

E No colour

II É EI
Ej age zno
 Reactions with Formaldehyde
Under different conditions different products are formed

nano t Imo
Lederer Manasse Reaction

Phenol on condensation with insufficient amount in presence

of Homo
called Novotel
of an lyst gives a linear

III
me
sI amE
so

In presence of excess of tech and a 504

basic 9 NH
at
higher p a different kind of condensation occurs This
ultimately results in the formation of 3 D_ Bakelite or
OH
104 PM

Haig
exam 4 I
I 412
Utz
I
42

Ii.EE.EE
Bakelite
Of Complete the following reactions

E oatho e para nitro phenol

OH

Kou
D A
are e
Major kno
o a
or Its ini
orangey

w u
EoI Iii
OH
h
EEE usui ai E t

OH OH
by I
a 407
Utz Br

a
O
Ehs Egg'Igafers iain
D SN2 Egg
I
OH
 DX i
CaoID

COOH

of Is
Alas
I OH
Ht
Identity A B and C in above reaction

took
2
a is sc D

GENCt
Es
EI is III
Benzene
diazonium
chloride

1MHz
Bralfelexcessly 0 U
E
gogo Liao's.edu
No B nice
Br K Br
Hspa
I 1
NOz NU z

I
 TcuBr
Br Br
nor B pr
Br
E Error
e
let
INHz LIO
Leja
Br
L

Ef Write the correct reactivity order with NaI for the following
compounds SNA

no
Eira
no o o
o
l

B c A

i
Electrophile will attack mainly at 4 position

I
0 t
a
05 a
430
1
B In Phenol

LH 1

E ET
The major product following men is
of the
µ
Ph i today g
Ph o
offs cusp
Minas 92
Minor

EI see EIIK
iEI.gg
010 which of the following will not give elterrescence with Naidoo
b d
Phenol Benzoic acid c 2,4 Dio phenol Picariucd
t Acidic strength
of Phenols
Orthoeffect is operative Benzoic acids and not in
only in co substituted
0 substituted phenols

iii Ein
OH

III III de
csammbfi.no p's D

OH OH
E a'Eo
LO Noa
INO

OH OH
Tien T
Loden
I
CN
OH

II IET l
OH

IIIa IIIa pKa 9002

ETI
go11
EE 9.28
 III EI 8.48 8.53
II
8.81
pKa 8.42

Reagent Ethanol Phenol

K H Lg Hug
NaOH No Rich Pho formed

PBR R Br Mo Rin

HB R Br Nu Rin
ne au nunn
SOU R U No Rx
Acoteltet Forms acetate formsacetate
Feds No Rich violet coloration
Kirso1142504 Oxidised toaldehyde neo Rim
 Source
Chem ucalgary.ca
 Nitrobenzene

conc
n
in
HssOy

a Iii
Felted

Line he
Azobenzene

na n

Hydrazobenzene

4
EEI.o.E.ie no

I
Reduction
NO
s
r

Moz

soil

Eos I FEET
 Br
Ii Bry
Br
MHz MHz
sai M

MHz INK Moz

H NHz
f NO
t
I
NO

I
51 47 2

Eoi I
me
Hinsberg
m sjnn.ph

I
Reagent
MHz
 If Aniline
Carbylamine Reaction i amines aliphatic aromatic on treating
with all KOH form isocyanide alsocalled carbylamine

20 and 30 amines don't undergo this reaction

Clea KOH

Reaction with Nitrous acid

I aromatic amines react with nitrousacid HNo unstable

to form aromatic diazonium salts This reaction is known as

diazotisation

j d mad t no

1 aliphaticamines also react with Halo acid to formdiazonium

salt but aliphatic diazonium salts are unstable and decompose
to give mix alkene
of alcohols 1421g

R mm
É R nice rote alkene t Ma
unstable