PHENOLS

Nomenclature
SYNOPSIS
Common IUPAC
Molecule name name
 Aromatic hydroxy compounds in which -OH
OH
group is bonded to benzene ring directly are
called phenols. Monohydroxy benzene is called Phenol Phenol
phenol. Phenol is also known as carbolic acid.
 Phenols are classified as monohydroxy,
OH
dihydroxy and trihydroxy compounds
CH3 2-methyl
OH OH OH o-cresol
Phenol
OH OH OH
OH

3-methyl
m-cresol
Phenol
monohydric dihydric trihydric CH3
 The simplest hydroxyl derivative of benzene is OH
phenol which is also its accepted IUPAC name.
4-methyl
 The hydroxyl derivatives of toluene are o–, m– p-cresol
Phenol
and p– cresol.
CH3
OH OH OH
OH
CH3 OH
Catechol Benzene-1,
2-diol

CH3 OH
CH3
Benzene-1,
o-cersol m-cersol p-cersol Resorcinol
3-diol
 Dihydroxy derivatives of benzene are called OH
benzene diols. OH
OH OH OH
OH Hydroquinol Benzene-1,
4-diol

OH
OH OH
HO OH
OH (Benzene 1,2,
Pyrogallol 3-triol)
Catechol Resorcinol Hydroquinol

 In phenols, the –OH group is attached to sp 2 OH

hybridized carbon of an aromatic ring. (Benzene 1,2,
Phloroglucinol
 The bond angle of C–O–H in phenol is 1090. 5-triol)
The carbon-oxygen bond length is 136 pm HO OH
OH
which is slightly less than that in methanol. This
H 3C CH3
is due to partial double bond character on 2,6-dimethyl
account of conjugation of unshared electronpair Phenol
of oxygen with the aromatic ring.
Methods of preparation: Phenol was first Physical properties: Phenol has higher
isolated from coaltar. boiling point than the arenes or haloarenes or
From Haloarenes: ethers of same molecular weight. It is due to the
formation of intermolecular hydrogen bond.
X  Compared relative to pure aromatic
hydrocarbons phenols are more soluble in water
 NaOH 350 C & 300 atm due to their ability to form hydrogen bonding
with water.
O Na OH  As the hydrocarbon part increases in size and
mass, the solubility decreases due to increasing
HCl of hydrophobic nature.
Chemical properties:
Acidic nature of phenol: Alcohols and
From Diazonium salt: phenols react with active metals like Na, K, Al
NH2

N2Cl
 etc to liberate hydrogen gas.
2ROH  2 Na  2RONa  H 2
 NaNO2  HCl 05 C 2 C6 H 5OH  2 Na  2C6 H 5ONa  H 2
OH  Phenols also react with aqueous NaOH solution
to produce the salt sodium phenoxide and water.
H2O2 warm N2  HCl
C6 H 5OH  NaOH  C6 H 5ONa  H 2O
 The acidic nature of alcohols is due to the polar
nature of O-H group.
From Benzene Sulphonic acid:  Electron releasing groups like alkyl groups
SO3H increase the electron density on oxygen and
decrease the polarity of O-H bond. This
conc.H2SO4,SO3 moltenNaOH decreases the acidic strength.
 Even though the electron releasing groups like
 CH 3 ,C 2 H 5 etc decrease the acidic strength
 
O Na O

HCl
of phenol, Phenol does not liberate CO2 with
 NaCl
Na 2CO 3 or NaHCO3 because phenol is weakly
From cumene:Phenol is manufactured from acidic than carbonic acid and carboxylic acids.
cumene (isopropyl benzene) Note: Acids stronger than carbonic acid, decomposes
CH3
Na2CO3 and NaHCO3 solutions liberating
CH(CH3)2 H3CCOOH
CO2 with brisk effervescence.
Relative acid strength: Carboxylic acid >
O2 (oxidation with air) Carbonic acid > Phenol > Methyl alcohol >
Water > Other alcohols
cumene hydroperoxide  The reactions of phenol with metals as well as
OH NaOH indicate that phenol is relatively more
acidic than alcohols and also water.


H / H2O C3COCH3 This is explained on the basis of the structure of
phenol.
 The hydroxyl group in phenol is directly pKa Values of some Phenols and Ethanol
attached to sp2 carbon of benzene ring. The sp2 Compound Formula pKa
carbon attached to ‘O’ being more
electronegative than sp3 carbon of alcohols, it o - Nitrophenol o  O2 N  C6 H 4  OH 7.2
decreases the electron density on oxygen.
m - Nitrophenol m  O2 N  C6 H 4  OH 8.3
Because of this oxygen develops still more
electron seeking character and releases proton p - Nitrophenol p  O2 N  C6 H 4  OH 7.1
by taking the shared pair of electrons with it.
 The acidic nature of phenol can also be Phenol C6 H 5  OH 10.0
explained on the basis of resonance stabilization
of phenoxide ion. o -Cresol o  CH 3  C6 H 4  OH 10.2
 Electron withdrawing groups present at ortho
m -Cresol m  CH 3C6 H 4  OH 10.1
and para positions (but not at meta) increases
the acidic nature of phenol. Gretaer the number p -Cresol p  CH 3  C6 H 4  OH 10.2
of such groups at ortho and para positions higher
is the acidic nature of phenol. Ethanol C2H5OH 15.9
 Electron releasing group present at ortho and
para positions (but not at meta) decreases the W.E-1: O - Nitro phenol is less acidic than
acidity of phenols. Greater the number of such P - nitro phenol. Give reason
groups at ortho and para positions lesser is the Sol. O - nitro phenol exist in intramolecular hydrogen
acidic nature of that phenol. bonds. So acidic nature is less.
 Acidic strength increases with the decrease of
the pK a values. Esterification of Phenol: Phenols react
 Order of acidic strength of phenols is as follows with carboxylic acids and their derivatives like
acid chlorides and anhydrides to form esters.
OH OH OH
This reaction is called Schotten-Baumann
O2N NO2
reaction.
> >
C6 H 5OH  RCOOH 
 C6 H 5  O  CO  R  H 2O
O2N NO2  During esteification H comes from phenol
NO2
3,5-dinitro
NO2 and ‘OH’ comes from carboxylic acid.
Picric acid phenol p-nitro
phenol C6 H 5OH  RCOCl 
pyridine

OH OH OH C6 H 5  O  CO  R  HCl
NO2
 Salicylic acid on acetylation gives acetyl
> > salicylic acid known as Aspirin.
COOH COOH
NO2
o-nitro m-nitro phenol OH OCOCH3
phenol phenol conc.H2SO4
 (CH3CO)2O
OH OH OH
CH3 acetyl salicylic
acid (aspirin)
> >
Electrophilic aromatic substitution
CH3 reactions of phenol:In phenol, -OH group
o-cresol CH3 o-cresol is ring activating and ortho and para directing
p-cresol as these positions get more electron density
 The greater the pKa value, the weaker the acid. through resonance.
 Nitration  When the reaction is carried out in solvents of
OH OH OH low polarity such as CHCl3 or CS2 and at low
NO2 temperature, monobromophenols are formed.
dil.HNO3
  Here no Lewis acids like FeBr3 are required
because highly activating effect of -OH group
O - nitrophenol polarises bromine quickly.
NO2
P - nitrophenol  Phenol reacts with bromine water and gives
1) Intramolecular 1) Intramolecular 2,4,6-tribromo phenol (white precipitate)
H bond H bond
2) Steam volatile 2) Less volatile
 In water phenol forms phenoxide ion which
activates the benzene ring.
 Nitration of phenol is gives a poor yield OH OH
because nitric acid also causes oxidation of Br Br
phenol. H 2O
Alternate method of nitration:- 3Br2
0-5C

Br
Reimer-Tiemann reaction: Phenol when
treated with chloroform in the presence of NaOH
gives salicylaldehyde.
Mechanism:
i) CHCl3  OH   H 2O  CCl3 : CCl2  Cl 
Dichloro carbene ( : CCl2 ) is the attacking
electrophile in this reaction :
 Phenol when treated with conc. HNO3 gives
2,4,6-trinitrophenol known as picric acid O O
OH OH H
O2N NO2
: CCl2
conc.HNO3 CCl2

O O OH
CHCl2 CH(OH)2 CHO
NO2 ii) 
NaOH H
 The yield in the reaction is poor. Now a days
picric acid is prepared by treating phenol with
conc. H 2SO 4 and then with conc. HNO3 . Salicylaldehyde

OH OH
SO3H
OH
 If CCl4 / KOH is used salicylic acid will be
O2N NO2

conc.H2SO4 conc.HNO3 formed

OH OH
CHCl2 COOH
SO3H NO2 CCl4, KOH, 
Picric acid

Halogenation:- H / H2O
OH OH OH Salicylic acid
Br
Br2 in CS2 at 0C
Kolbe’s reaction: Phenoxide ion generated
 by treating phenol with sodium hydroxide is
even more reactive than phenol towards
Br electrophilic aromatic substitution.
 Uses of Phenol: It is a raw material for the
OH ONa manufacture of important dyes, drugs and
pharmaceuticals.
NaOH O=C=O
 2,4-dichloro-3,5 dimethyl phenol is used as
powerful antiseptic under the name Dettol.
ONa OH  It is used in the manufacture of drugs like
COO COOH Aspirin, Salol etc.
H  0.2% aqueous Phenol is used as an antiseptic.
H
 Phenol on reaction with urea and formal dehyde
(major) gives condensation regin (PVF) used as wood
2-hydroxy benzoic acid adhesives.
(Salicylic acid)
Tests of Phenol:
 If KOH is used parahydroxy benzoic acid will i) Phenol in water gives violet colour with a drop
be formed as major product. of FeCl3 .
Action of Zinc dust:Phenol on heating ii) Phenol in water gives white precipitate with
with zinc dust produces benzene. bromine water.
OH iii) Phenol gives blue colour indophenol with
ammonia and sodium hypochlorite.
 Zn  ZnO W.E-2:Give equations of the following reactions:
(i) Reaction of propene with mercuric acetate
Oxidation: Phenol on oxidation with chromic followed by hydrolysis.
acid ( Na 2Cr2O7  H 2SO 4 ) produces benzoquinone, (ii) Oxidation of propan-1-ol with alkaline
which is a conjugate diketone. In the presence KMnO4 solution
of air, phenols are slowly oxidised to dark (iii) Reaction of bromine in CS2 with phenol
coloured mixtures containing quinones. (iv) Action of dilute HNO3 with phenol
OH O Sol. (i) CH3  CH  CH 2 + Hg(OAc)2 + H2O 

propene

 CH3  CH  CH3
NaBH 4
chromic acid CH3  CH  CH 2 
H2CrO4 | | |
OH HgO OH
O (ii) CH3 – CH2 – CH2OH + 2[O]   CH3
Alk. KMnO 4
benzoquinone 
– CH2 – COOH + H2O
Fries rearrangement:
OH OCOCH3 OH OH OH
Br
anhydrous AlCl3 Br4
 (CH3CO)2O  OH OH
(in CS2)
(iii)
dil.)
OH OH Br (Major)
COCH3 (Major)
AlCl3 NO
OH OH
 OH
Rearrangement NO2

O-hydroxy dil.)  H2O

acetophenone COCH3 (iv)
P-hydroxy
acetophenone NO2
OH
NO2

H2O
W.E-3:You are given benzene, conc. H2SO4 and 7. Phenol is
NaOH. Write equations for the preparation of 1. a base weaker than ammonia
phenol using these reagents. 2. an acid stronger than carbonic acid
SO 3H 3. an acid weaker than carbonic acid
4. a neutral compound
H 2SO 4 (conc.) 8. Phenol reacts with bromine in carbon
  disulphide at low temperature to give
SO 3Na 1. m-bromophenol
2. o- and p-bromophenol
NaOH
 
3. p-bromophenol 4. 2,4,6-tribromophenol
9. Phenol is less acidic than
ONa
1. p-nitrophenol 2. ethanol
 fusion 3. cresol 4. benzyl alcohol
Sol. Na 2SO 3
 2NaO  10. Phenol on treatment with conc. HNO3 gives
OH 1. picric acid 2. o-and m-nitrophenols
3. cresol 4. resorcinol
dil. HCl
H 2O
NaCl LEVEL-I (C.W) - KEY
1) 3 2) 3 3) 1 4) 4 5) 1 6) 4 7) 3
LEVEL-I (C.W) 8) 2 9) 1 10) 1

METHODS OF PREPARATION LEVEL-I (C.W) - HINTS

1. Phenol is also called 1. Phenol also known as carbolic acid
1. salicylic acid 2. benzyl alcohol
OH
3. carbolic acid 4. salol
2. Benzene diazonium chloride on hydrolysis 2. +
C6H5N2Cl  
2 H O
gives warm + N2 + HCl
1. Benzene 2. Benzyl alcohol
3. Phenol 4. Chlorobenzene 3. Picric acid
NOMENCLATURE OH OH
3. Which does not have a carboxyl group? Br Br
1. Picric acid 2. Ethanoic acid + 3Br2 
3. Aspirin 4. Benzoic acid 4.
PROPERTIES
Br
4. When phenol is treated with excess of
bromine water, it gives 5. Sodium bicarbonate
1. m-bromophenol 2. o- and p-bromophenol 6. It is Reimer Tiemann reaction
3. 2,4-dibromophenol 4. 2,4,6-tribromophenol 7. PKa of phenol = 10
5. Phenols does not react with PKa of carbonic acid is less than 10
1. sodium bicarbonate 2. sodium hydroxide
OH OH OH
3. potassium hydroxide 4. ferric chloride Br
i ) CHCl / NaOH
   3   Br in CS
6. Phenol ii ) H 
Salicylaldehyde. This 
2 2 +
8.
reaction is known as
1. Gattermann aldehyde synthesis Br
2. Sandmeyer’s reaction 9. PKa of phenol is 10
3. Perkin’s reaction 4. Reimer-Tiemann reaction 10. Picric acid
 9. Br2 dissolved in CS2 reacts with phenol at
LEVEL-I (H.W) 273K to give ..... as the major product
1) o - Bromophenol 2) m - Bromophenol
METHODS OF PREPARATION 3) p - Bromophenol 4) 2,4,6-Tribromophenol

1. Cumene  i ) O2
ii ) H O/ H
(X) and (Y) LEVEL-I (H.W) - KEY
2

(X) and (Y) respectively are 1) 3 2) 3 3) 2 4) 2 5) 2 6) 2 7) 2

1. toluene, propene 2. toluene, propylchloride 8) 4 9) 3
3. phenol, acetone 4. phenol, acetaldehyde
2. NaNO  HCl / O C
In the reaction C6 H 5 NH 2  LEVEL-I (H.W) - HINTS
X
o
2

CH3 CH3

H2O, warm
Y . ‘Y’ is
H3C – CH H3C – C – O – OH OH
1) C6 H 5Cl 2) C6 H 6 3) C6 H 5OH 4) C 6 H 5CHO

O

2 
H O
H
+ CH3COCH3
NOMENCLATURE 1. 2

3. Picric acid is a yellow coloured compound. X Y

Its chemical name is phenol acetone
1. m-nitrobenzoic acid 2. 2,4,6-trinitrophenol +

3. trinitrotoluene 4. trinitroaniline
PROPERTIES NaNO2  HCl
  H O

warm 
2. 0 5C
2

4 C6 H 5OH  CHCl3  NaOH salicylaldehyde

The electrophile involved in the above
3. 2, 4, 6 - trinitro phenol
reaction is.
 4. H 2O  CCl3  : CCl2  Cl 
1. dichloromethyl cation (C HCl2 )
electrophile (dichloro carbene)
2. dichlorocarbene (: CCl 2 ) 6. phenols are acidic in nature
3. trichloromethyl anion (CCl3 ) 7. cresols are less acidic than phenol

8. Kolbe’s reaction
4. formyl cation (C HO) 9. monobromo phenols are formed
5. The reaction,
C6 H 5ONa  CO2  H 2O  C6 H 5OH  NaHCO3
suggest that
1) Phenol is a stronger acid than carbonic acid
2) Carbonic acid is a stronger acid than phenol
3) Water is stronger acid than phenol
4) None of the above
6. Which of the following compounds when
dissolved in water, gives a solution with pH
less than seven ?
1) CH 3COCH 3 2) C6 H 5OH 3) C6 H 5 NH 2 4) C2 H 5OH
7. Increasing pKa values of o-, m- and p- cresols is
1) o<p<m 2) m<p=o 3) m<o<p 4) p<o< m
8. Identify the product Z in the following
sequence of reactions

phenol 
NaOH
 X  CO2
4  7 atm ,410 K
 Y 
H 3O
Z
1) Aspirin 2) Salicyladehyde
3) Benzoic acid 4) Salicylic acid
 P-nitrophenol
2) 4-Hydroxybenzene-1,3-disulphonic acid,
picric acid
3) 4-Hydroxybenzene-1,3-disulphonic acid,
PHENOLS 2,4-dinitrophenol
4) 3-Hydroxybenzene sulphonic acid, picric acid
LEVEL-II (C.W) 9. Phenol 
NaOH
 A 
1) CO2
2) H 
 B 
( CH 3CO ) 2 O
H
C
Incorrect statement among the following is
1) Preparation of ‘B’ from phenol is called
PROPERTIES OF PHENOL Kolbe’s reaction
1. Phenol (1 mole) reacts with bromine water 2) ‘B’ is steam volatile
to give sym.tribromophenol. The amount of 3) ‘C’ has a free -OH group of ‘B’
bromine required is 4) ‘C’ can be used as antiiflammatory, analgesic
1. 3.0 mole 2. 1.5 mole 3. 4.5 mole 4. 6.0 mole and antipyretic.
2. The most acidic compound among the
following is LEVEL-II (C.W) - KEY
1 phenol 2. ethanol 1) 1 2) 3 3) 2 4) 1 5) 4 6) 4 7) 2
3. 3,5-dinitrophenol 4.4-methoxy phenol
8) 2 9) 3
3. Which one of the following compounds would
undergo nitration with greatest ease LEVEL-II (C.W) - HINTS
1. benzene 2. phenol 1. Phenol required 3 moles of bromine
3. nitrobenzene 4. benzoic acid 2. If – NO2 is present on the benzene ring of
4. Phenol on distilling with zinc dust gives phenols acidic strength increases particularly
1. benzene 2. diphenyl ether when that group is at ortho (or) para positions.
3. diphenol 4. zinc phenoxide 3. PKa of phenol is 10
5. Salicylic acid is produced when phenol in
alcoholic KOH is treated with 4. C6 H5OH 
Zn

C6 H6  ZnO
1. CH 3Cl 2. CHCl3 3. CH 2Cl2 4. CCl4
6. In the fololwing compounds, the decreasing
order of acidity is  CCl4 
KOH

+3NaOH
–NaCl

5.

H O
1. I > IV > III > II 2. II > IV > I > II 
2
HCl
3. II > I > III > IV 4. IV > III > I > II
7. Which order is correct about acidity 6. The correct order of acidity IV > III > I > II
1. CH 3COOH  C6 H 5COOH  C6 H 5OH 7. The correct order of acidity
2. C6 H 5COOH  CH 3COOH  C6 H 5OH C6 H 5COOH  CH 3COOH  C6 H 5OH
3. C6 H 5OH  C6 H 5COOH  CH 3COOH
4. C6 H 5OH  CH 3COOH  C6 H 5COOH
8. Phenol 
conc . H SO
2 4
A 
conc . HNO
3
 B Here A and B 8. A is
are respectively.
1) P-Hydroxy benzenesulphonic acid,
9. ‘B’ is salicyclic acid one that would react fastest with conc. HCl and
anhydrous ZnCl2 is
1) 1-Butanol 2) 2-Butanol
3) 2-Methylpropan-2-ol 4)2-Methylpropanol-1
1. One mole of aniline warmed with the mixture LEVEL-II (H.W) - KEY
of NaNO2  HCl . If we assume 100% yield, 1) 2 2) 4 3) 3 4) 3 5) 2 6) 2 7) 4 8) 4 9) 3
volume of N 2 gas liberated at S.T.P is LEVEL-II (H.W) - HINTS
1) 11.2L 2) 22.4 L 3) 33.6 L 4) 44.8 L 1. 22.4 L
2. Phenol reacts with which one of the following 2. Conjugate diketone is known as benzoquinone.
reagents gives a conjugate diketone will be 3. acetylation
formed ? 4. picric acid
1) Na2Cr2O7 2) conc.HNO3 5. presence of electron with drawing group at o-
and p- positions
3) Zn,  4) Na2Cr2O7  H 2 SO4 6. 22.4 L
3. The reaction, 7. CO2, CO2
C6 H 5OH 
CH 3COCl
Pyridine
 C6 H 5OCOCH 3 8. tertiary alcohol
is called PREVIOUS EAMCET QUESTIONS
1) Reimer-Tiemann reaction 1. The conversion of O -acylated phenol in
2) Schotten-Baumann reaction presence of AlCl3 to P - acylated phenol is an
3) Acetylation 4) Benzoylation example for this type of organic reaction.
4. Which of the following is most acidic ? 1) Addition reaction 2) Substituion reaction
1) Phenol 2) CH 3CH 2OH 3)Molecular rearrangement 4)Elimination reaction
3) Picric acid 4) p-Nitrophenol PREVIOUS EAMCET - KEY: 1) 3
5. The descending order of k b values of the
following compounds is LEVEL-II (H.W)

PROPERTIES OF PHENOL
a) b) c) d) 1. Benzenediazonium chloride on reacting with
phenol in weakly basic medium gives
1. benzene 2. chlorobenzene
1) d > b > c > a 2) a > c > b > d 3. diphenyl ether 4. p-hydroxy azobenzene
3) b > d > c > a 4) a > c > d >b 2. The reaction
6. One mole of aniline warmed with the mixture
of NaNO2  HCl . If we assume 100% yield,
+ ClCOC6H5  is known as
volume of N2 gas liberated at S.T.P is
1) 11.2L 2) 22.4L 3) 33.6L 4) 44.8L
1. Wurtz reaction 2. Kolbe reaction
7. When benzene sulphonic acid and p-
3. Rimer-Tiemann reaction
nitrophenol are treated with NaHCO3, the
4. Schotten-Baumann reaction
gases released respectively are
3. Phenol is
1) SO2 , NO2 2) SO2 , NO 3) SO2 , CO2 4) CO2 , CO2 1. a neutral compound
8. Phenol is heated with a solution of mixture 2. a base weaker than ammonia
of KBr and KBrO 3. The major product 3. an acid stronger than carbonic acid
obtained in the above reaction is : 4. an acid weaker than carbonic acid
1) 2-Bromophenol 2) 3-Bromophenol Phenol  Zn
 A 
conc.HNO3
 B 
Zn
C
4. distillation conc.H SO at 600C NaOH
3) 4-Bromophenol 4) 2,4,6-Tribromophenol 2 4

9. From amongest the following alcohols, the In the above reaction, compounds (A), (B)
 and (C) are respectively
1. benzene, nitrobenzene and hydrazobenzene LEVEL-III
2. benzene, nitrobenzene and aniline
3. benzene, dinitrobenzene and m-nitroaniline
1. When phenol reacts with chloroform and an
4. toulene, m-nitrobenzene and m-toulidine
alkali, the compounds formed is
5. Sodium phenoxide when heated with CO2
salicylaldehyde. If pyrene is used in place of
under pressure at 1250 C gives chloroform, the product obtained is
1. salol 2. salicylaldehyde 1. Salicylic acid 2. Salicylaldehyde
3. sodium benzoate 4. sodium salicylate
3. Phenolphthalein 4. Cyclo hexanol
6. Salol prepared from (internal antiseptic)
1. salicylic acid and methyl alcohol 2. The most suitable method of separation of
2. salicylic acid and phenol equal (1:1) mixture of o-and p-nitrophenols is
3. both 1 and 2 4. asprin and phenol 1. Crystallisation 2. Distillation
3. Sublimation 4. Chromatography
LEVEL-III - KEY
1) 4 2) 4 3) 4 4) 1 5) 4 6) 2 1. Both A and R are correct and R is correct
explanation of A
LEVEL-III - HINTS 2. Both A and R are correct but R is not the
__

1. C6 H 5 N 2Cl  C6 H 5OH 

OH
C6 H 5  N  N  C6 H 5  OH correct explanation of A
2. Schotten - Baumann reaction 3. A is correct but R is in correct
3. Phenol is a weaker acid then carbonic acid. 4. A is in correct but R is correct
4. A  C6 H 6 , B  C6 H 5 NO2 C=Hydrazobenzene 3. Assertion (A): o-phenol sulphonic acid on
heating at 1000 C changes to p-phenol
sulphonic acid.
5. + CO2
Reson (R): Sulphonation of phenol is a
reversible process.
6. Salol is obtained form salicylic acid and phenol. 4. Assertion (A) : Phenol and benzoic acid can be
PREVIOUS MAIN QUESTIONS distinguished by NaOH.
1. Sodium phenoxide when heated with CO2 under Reson (R): Benzoic acid is stronger acid than
phenol
pressure at 1250 C yields a product which on 5. Asseriton (A): Phenol is more reactive than
acetylation produces C. benzene towards electrophilic substitution.
Reson (R): In the case of Phenol, the
125C  intermediate Carbocation is more resonance
 CO2 
5atm  B 
AC2O  C
H . stabilized.
6. Assertion (A): p-Nitrophenol is stronger acid
The major product C would be than o-nitrophenol
Reson (R) Intramolecular hydrogen bonding
makes ortho - isomer weaker acid than para
1) 2) - isomer.
7. Assertion (A) : Phenol is more reactive than
benzene towards electrophilic reactions.
Reason (R) : The +R effect of OH group
increases the electron density on benzene
nucleus.
3) 4) 8. Assertion ( A) : Phenols are more acidic than
aliphatic alcohols.
Reason (R) : Phenoxides are stabilized by
resonance.
PREVIOUS MAIN - KEY : 1) 3
 LEVEL-IV - KEY
1) 1 2) 2 3) 2 4) 4 5) 1 6) 1 7) 1 8) 1

LEVEL-IV - HINTS

1. + CCl2 + 4NaOH

(Final product)
2. o- and p-nitrophenols differ in boiling points.
o-nitrophenol is steam volatile
3 . During sulphanation of phenol at law
temparature ortho isomer is major products
where as at 1000 C , it gives mainly para isomer..
4. Both Benzoic acid, phenol react with NaOH.
5. Conceptual.
6. P-nitro phenol is more acidic than o-nitro
phenol.
7. –OH group in phenol is ring activating and ortho
para directing
8. Phenoxide ions are stabilised by resonance but
alkoxide ions are not stabilised by resonance
LEVEL-IV