11.

ALCOHOLS, PHENOLS AND ETHERS

Can you recall ?
Do you know ?
1. What is the name and formula
of 2nd member of homologous Epoxide are cyclic ethers in which
series of alcohols? the ethereal oxygen is a part of a
2. What is the structural formula of three membered ring.
functional group of ether? C C H 2C CH2
O O
3. What is the name of the compound
having -OH group bonded to benzene (Ethylene oxide) (1,2 - Epoxyethane)
ring?

11.1 Introduction : Alcohols are organic 11.2 Classification : Let us first consider
compounds whose molecules contain hydroxyl classification of alcohols, phenols and then
group, (-OH) attached to a saturated carbon ethers.
atom. 11.2.1 Mono, di, tri and polyhydric
C OH compounds : Alcohols and phenols are
classified as mono, di-, tri, or polyhydric
Hydroxyl group can also be present in aromatic
compounds on the basis of one, two, three
compounds. There are two types of aromatic
or more hydroxyl groups present in their
hydroxy compounds: phenols and aromatic
molecules as :
alcohols. Phenols contain a hydroxyl group
directly attached to the carbon atom of benzene CH3 - CH2 - OH H2C - OH H2C - OH
ring. When the hydroxyl group is present in the H2C - OH HC - OH
side chain of aromatic ring, the compound is H2C - OH
termed as aromatic alcohol.
OH OH
OH
OH OH
OH OH
OH
Monohydric Dihydric alcohols/ Trihydric
Phenols alcohols/phenols phenols alcohols/phenols

CH2-OH Monohydric alcohols are further classified on

the basis of hybridisation state of the carbon
atom to which hydroxyl group is attached.
Aromatic alcohol
a. Alcohols containing sp3C - OH bond : In
Ethers are compounds which contain these alcohols -OH group is attached to a sp3
an oxygen atom bonded to two alkyl groups hybridised carbon atom of alkyl group. These
or two aryl groups or one alkyl and one aryl alcohols are further classified as primary (10),
group. Ethers are organic oxides. Ethers are secondary (20) and tertiary (30) alcohols in which
considered as anhydrides of alcohols. -OH group is attached to primary, secondary
and tertiary carbon atom respectively. (see
R-O-R', R-O-Ar, Ar-O-Ar'.
Fig. 11.1), refer to Std. XI Chemistry Textbook
Chapter 14, sec. 14.3.2)

234
 Primary
b. Alcohols contianing sp2C -OH bonds :
H Secondary
carbon R carbon In these alcohols -OH group is attached
R C OH R C OH to a sp2 hybridised carbon atom which is part of
H H a carbon-carbon double bond. These alcohols
10 alcohol 20 alcohol are known as vinylic alcohols. For example
tertiary CH2 = CH - OH (Vinyl alcohol)
R carbon
11.2.2 Classification of Ethers : Ethers are
R C OH
classified as symmetrical ethers (simple
R ethers) or unsymmetrical ethers (mixed
30 alcohol
ethers) depending on whether the two alkyl/
Fig. 11.1 : Primary, secondary and tertiary aryl groups bonded to oxygen atom are same
alcohols or different respectively. For example :
Each of these three types of alcohols can also R - O - R/Ar - O - Ar
be either allylic or benzylic if the sp3 carbon
carrying -OH is further bonded to sp2 carbon. CH3 - O - CH3/ C6H5 - O - C6H5
symmetrical ethers (simple ethers)
• Allylic alcohols : In this type of alcohols
-OH group is attached to sp3 hybridised R - O - R'/Ar - O - Ar'
carbon atom which is further bonded to a
carbon-carbon double bond. Allylic alcohol CH3 - O - C2H5/C6H5 - O - CH3
may be primary, secondary or tertiary. unsymmetrical ethers (mixed ethers)

• Benzylic alcohols : In this type of alcohols 11.3 Nomenclature :

-OH group is attached to sp3 hybridised 11.3.1 Alcohols : There are three systems of
carbon atom which is further bonded to an nonmenclature of monohydric alcohols.
aromatic ring. Benzylic alcohol may be
a. Common/trivial names : The common
primary, secondary or tertiary.
or trivial names of alcohols are obtained by
adding word alcohol after the name of alkyl
group bonded to -OH. Names of higher alkyl
Use your brain power groups also include prefixes like normal, iso,
Classifiy the following secondary, tertiary (see. Table 11.1).
alcohols as 10 / 20 / 30 and allylic/ b. Carbinol system : In this system alcohols
benzylic are considered as derivatives of methyl
CH3
H2C = CH - CH2 - OH, alcohol which is called carbinol. The alkyl
group attached to the carbon carrying -OH
H2C = CH - CH - OH, group are named in alphabetical order. Then
CH3 the suffix carbinol is added. For example :
CH3 H Carbinol carbon
H2C = CH - C - OH, H 3C C OH
CH3 H
Methyl carbinol
CH3
CH2 OH CH OH

235
 11.3.2 Nomenclature of phenols : The
Use your brain power hydroxyl derivative of benzene is called
Name t-butyl alcohol using phenol. The IUPAC system name of phenol is
carbinol system of nomenclature. benzenol. The common name phenol is also
accepted by IUPAC. The common names have
c. IUPAC system : Accoriding to IUPAC
prefixes ortho, meta and para in subsituted
system (Std XI Chemistry Text book, Chapter
phenols. IUPAC system uses the locant 2-, 3-,
14), alcohols are named as alkanols. The
4-, etc. to indicate the positions of substituents
ending ‘e’ in the name of the parent alkane,
(see Table 11.2).
alkene or alkyne is replaced by the suffix
‘ol’. For naming polyhydric alcohol, ‘e’ in the 11.3.3 Nomenclature of Ethers : In the
ending of alkane is retained, the ending ‘ol’ is common system of nomenclature, the ethers
added and number of -OH groups is indicated are named by writing names of the alkyl groups
by prefix di, tri, etc., before ‘ol’. The positions attached to the oxygen atom in alphabetical
of -OH groups are indicated by appropriate order and word ether is added. If two alkyl
locants. For example ethane -1,2-diol (see. groups are same, prefix di- is used. According
Table 11.1). Similarly cyclic alcohols are to the IUPAC system of nomenclature, ethers
named by using prefix cyclo to the parent are named as alkoxyalkanes (see Table 11.3).
alkane and considering -OH group attached to The larger alkyl group is considered to be the
C-1 carbon atom. parent alkane. The name of the smaller alkane
is prefixed by the name of alkoxy group and its
locant. For example :
OH
C2H5 Some alkoxy group
1 CH3-CH2O- Ethoxy
OH CH3
Cyclobutanol 2- Ethylcyclopentanol 2 3 CH3-CH2-CH2-O- n-Propoxy
CH3 - O - CH - CH3 CH3-CH-O- Isopropoxy
CH3
2-Methoxypropane
Table 11.1 Common/Trivial and IUPAC Names of some alcohols
Structural formula Common/ Trivial Name IUPAC Name
H3C-OH Methyl alcohol Methanol
H3C-CH2-OH Ethyl alcohol Ethanol
H3C-CH2-CH2-OH n -Propyl alcohol Propan -1-ol
H3C-CH2-CH-OH sec-Butyl alcohol Butan -2-ol
CH3
H3C-CH-CH2-OH Isobutyl alcohol 2- Methylpropan-1-ol
CH3
CH3 tert-Butyl alcohol 2-Methylpropan-2-ol
H3C C OH
CH3
H2C CH2 Ethylene glycol Ethane-1, 2-diol
OH OH
H2C − CH − CH2 Propylene glycerol Propane-1,2,3-triol
OH OH OH
H3CCH = CHCH2OH Crotonyl alcohol But-2-en-1-ol

236
 Table 11.2 Common and IUPAC names of some phenols

Structural formula Common name IUPAC Name

OH
Phenol Benzenol/Phenol

OH
CH3
o- Cresol 2-Methylphenol

HO
p-Nitrophenol 4-Nitrophenol
NO2
OH
OH
Catechol Benzene-1,2-diol

OH
Resorcinol Benzene-1,3-diol
OH
HO
Hydroquinone/
Benzene -1,4-diol
quinol
OH
OH
Phloroglucinol Benzene-1,3,5-triol
HO OH
OH
HO OH
Pyrogallol Benzene-1,2,3-triol

Table 11.3 Common and IUPAC Names of some Ethers

Structural formula Common Name IUPAC Name

H3C - O - CH3 Dimethyl ether Methoxymethane
H3C - O - CH2 - CH3 Ethyl methyl ether Methoxyethane
H3C - O - CH2 - CH2 - CH3 Methyl n-propyl ether 1-Methoxypropane
C6H5 - O - CH3 Methyl phenyl ether (Anisole) Methoxybenzene
O - CH2 - CH2 - CH3
Phenyl n-propyl ether 1- Propoxybenzene

CH3
H3C OCH3 2- Methoxy-1,1-
-
dimethylcyclobutane

237
 alcohol. (Refer to Std. XI Chemistry Textbook
Problem 11.1 : Draw structures of
following compounds. section 15.2.4). This is an antimarkownikoff
hydration of alkene.
i. 2,5-Diethylphenol ii. Prop-2-en-1-ol
iii. 2-methoxypropane iv. Phenylmethanol Do you know ?
The mechanism of acid catalyzed
Solutuion : hydration of alkene involves the
i. OH ii.
3 2 1
following three steps:
1 C2H5
6 H2C = CH - CH2 - OH H
2
5 H - O - H + H⊕ H-O-H
H5C2 3 ⊕
4 Step 1: Formation of carbocation
iii. CH3-CH-CH3 iv. CH2 - OH intermediate.
O-CH3 H
H-O-H+ C=C H2O + C - C
⊕ ⊕
H
Try this... Step 2: Nucleophilic attack of H2O on C⊕
Write IUPAC names of the H
following compounds. C-C +H-O C-C
OH ⊕
i. ii. H3C-CH-CH2- CH3 H H O⊕
OH OCH2- CH3 H H
Step 3: Deprotonation
iii. CH2 - CH2 - OH iv. H C OH H2O
3 C-C C-C + H3O⊕
H O⊕ H OH
H H
11.4 Alcohols and Phenols : Use your brain power
11.4.1 Prepartion of alcohols : Predict the major product of the
a. From alkyl halide by hydrolysis with following reactions :
aqueous alkali or moist silver oxide (refer to • CH3 - CH = CH2
(i)B2H6 - THF
?
(ii)H2O2, OH
section 10.6.2)
b. By acid catalyzed hydration of alkenes : • CH3 (i) con. H2SO4 ?
(ii) H2O
Alkene reacts with sulfuric acid to produce
alkyl hydrogen sulfate, which on hydrolysis
gives alcohol (Refer to Std XI Chemistry d. By reduction of carbonyl compounds :
Textbook, section 15.2.4). This reaction i. By reduction of aldehydes and ketones :
follows Markownikoff’s rule.
Aldehydes on reduction by H2/Ni or
c. Hydroboration - Oxidation of alkenes : LiAlH4 give primary alcohols (10). Similarly
With diborane (B2H6) alkene undergoes ketones on reduction with H2/Ni or LiAlH4
addition reaction (Hydroboration) to give to give secondary alcohols (20).
trialkylborane (R3B), which on oxidation with H2/Ni or Pd
∆
hydrogen peroxide in alkaline medium gives R - CHO (i) LiAlH4 R- CH2 - OH
(ii) H3O ⊕ 10 alcohol

238
 O H2/Ni or Pd
∆ R CH OH Problem 11.2 : Predict the products for the
R C R (i)LiAlH4
R following reaction.
(ii) H3O⊕
20 alcohol ?
H2/Ni

ii. By reduction of carboxylic acids : CH3 - CH = CH - CH2 - CHO

(A) (i) LiAlH4 ?
Caboxylic acids require strong reducing agent (ii) H3O⊕

like LiAlH4 to form primary alcohols. Solution : The substrate (A) contains an
isolated C = C and an aldehyde group.
O
(i) LiAlH4 H2/Ni can reduce both these functional
R C OH (ii) H3O⊕
R - CH2 - OH groups while LiAlH4 can reduce only -CHO
of the two, Hence
However LiAlH4 is an expensive reagent.
Therefore, commercially acids are first H 2/
Ni CH3-CH2-CH2-CH2-CH2-OH
transformed into esters which on catalytic (A) (i
)L
hydrogenation give primary alcohols. (ii) iAlH
H O⊕ 4
CH3-CH=CH-CH2-CH2-OH
3

H⊕
R - COOH + R'OH R - COOR' + H2O
Ni/Pd
This reaction is useful in synthesis of a variety
RCOOR' + 2H2 ∆
R - CH2OH + R'OH of alcohols (see Table 11.4).
Table 11.4 Preparation of alcohols by Grignard
Remember... reagent
The advantage of LiAlH4 over Aldehyde/ Grignard Type of
Final product
H2/Ni is that it does not reduce the ketone reagent alcohol
isolated olefinic bond and hence it can H - CHO
R - Mg X R - CH2OH 10
reduce unsaturated aldehyde and ketones to (formaldehyde)
unsaturated alcohols. R' - CHO R - CH - OH
R - Mg X 20
(aldehyde) R'
e.By addition of Grignard reagent to R''
aldeheydes and ketones : Grignard reagent R' - CO - R''
R - Mg X R - C - OH 30
reacts with aldehyde or ketone to form an (ketone)
adduct which on hydrolysis with dilute acid R'
gives the corresponding alcohols.
δ Do you know ?
O OMgX
δ δ⊕
δ⊕C + R - Mg - X dry
Epoxide reacts with Girgnard
ether -C-
R reagent followed by acidic hydolysis
to give primary alcohols
(adduct) dry
H2C - CH2 + R Mg X ether
OH
H3O⊕ X O
- C - + Mg
H3O⊕
R OH [R - CH2- CH2 - OMgX]
X
R-CH2CH2-OH + Mg
OH

239
11.4.2 Preparation of phenol : d. From aniline : Aniline is treated with nitrous
acid [NaNO2 + HCl] at low temperature to
a. From chlorobenzene (Dow Process) :
obtain benzene diazonium chloride, which on
Chlorobenzene is fused with NaOH at high
hydrolysis gives phenol (Also refer to chapter
temperature and pressure (623K and 300atm)
13 for this reaction).
followed by treatment with dilute HCl to
obtain phenol.
NH2 ⊕
⊕ N2Cl
Cl O Na OH
NaNO2
NaOH + HNO2 HCl
623 K/300atm H3O⊕ 273 K
(Aniline) (Benzene diazonium
(Chloro (Sodium (Phenol) chloride)
benzene) phenoxide)
b. From Cumene : This is the commercial OH
method of preparation of phenol. Cumene H2O
(isopropylbenzene) on air oxidation in ∆
+ N2 + HCl
presence of Co-naphthenate gives cumene (Phenol)
hydroperoxide, which on decomposition with
dilute acid gives phenol with acetone as a 11.4.3 Physical Properties of alcohols and
valuable by product. phenols
CH3 CH3
H3C CH H 3C C O O H Try this...
Co-naphthenate Arrange O-H, C-H and N-H
+ O2 423K bonds in increasing order of their
bond polarity.
(Cumene) (air) (Cumene hydroperoxide)
a. Nature of intermolecular forces : Alcohols
OH CH3 and phenols are very polar molecules due to
C=O presence of -OH groups. The polar -OH groups
dil. HCl
∆
+ CH3 are held together by the strong intermolecular
(Phenol) (Acetone)
forces, namely hydrogen bonding.

c. From benzene sulfonic acid : Benzene δ⊕ δ - δ⊕ δ - δ⊕ δ - δ⊕ δ -

sulfonic acid on neutralization by NaOH H-O H-O H-O H-O
gives sodium benzene sulfonate, which on R R
fusion with solid NaOH at 573 K gives sodium
phenoxide, followed by reaction with dilute Intermolecular (phenol)
(alcohol)
acid gives phenol. ⊕ hydrogen bonding
SO H SO3Na
3
b. Physical State : Lower alcohols are
NaOH
colourless, toxic liquids having characterstic
alcoholic odour. Pure phenol is colourless,
(Benzene sulphonic acid) (Sodium benzene sulphonate) toxic, low melting solid having characterstic
⊕ carbolic or phenolic odour.
O Na OH
c. Boiling Points : The boiling points of
NaOH dil. HCl
573 K alcohols and phenols increase with increase in
their molecular mass (Table 11.5).
(Sodium phenoxide) (Phenol)

240
 Table 11.5 M.P/B.P and solubilities of some alcohols and phenols
Name Formula M.P. (0C) B.P. (0C) Solubility (g/100g H2O)
Methyl alcohol H3C-OH -97 65 0.793
Ethyl alcohol H3C-CH2-OH -115 78 0.789
n-Propyl alcohol H3C-CH2-CH2-OH -126 97 0.804
Isopropyl alcohol H3C-CH-OH -86 83 0.789
CH3
n-Butyl alcohol H3C-CH2-CH2-CH2-OH -90 118 0.810
Isobutyl alcohol H3C-CH-CH2-OH -108 108 0.802
CH3
sec-Butyl alcohol H3C-CH2-CH-OH -114 99.5 0.806
CH3
tert-Butyl alcohol H3C 25.5 83 0.789
H3C C-OH
H3C
Phenol 41 182 9.3
OH

p-Cresol 35 202 2.3

H3C OH

o-Nitrophenol OH 45 217 0.2

NO2
p-Nitrophenol 114 - 1.7
O2N OH

d. Solubility : Phenols and lower alcohols

Problem 11.3 : The boiling points of n-butyl (having upto three carbons) show appreciable
alcohol, isobutyl alcohol, sec-butyl alcohol solubility in water due to their ability to form
and tert-butyl alcohol are 1180C, 1080 C.
intermolecular hydrogen bonding with water
99.50C and 830C respectively. Explain.
molecule (See Table 11.5).
Solution : As branching increases
intermolecular van der Waal’s force become δ⊕ O δ⊕ O
weaker and the boiling point decreases. δ- H H δ- H H
Therefore n-butyl alcohol has highest R-O δ ⊕ Ar-O δ ⊕
boiling point 1180C and tert-butyl alcohol H Oδ - H H Oδ - H
Hydrogen
has lowest boiling point 830C. Isobutyl Hydrogen H bond H
alcohol is a primary alcohol and hence its bond Intermolecular hydrogen bonding
boiling points is higher than that of sec- of R-OH and Ar-OH with water
butyl alcohol.

241
 Ar - OH + NaOH(aq) Ar-O Na⊕(aq)
Problem 11.4 : The solubility of o-nitrophenol
+ H2O(l)
and p-nitrophenol is 0.2 g and 1.7 g/100 g of
H2O respectively Explain the difference. Ar - O Na⊕(aq) + HCl(aq) Ar - OH↓
+ NaCl(aq)
Solution :
δ-
O δ⊕ Do you know ?
H (intramolecular hydrogen Sodium bicarbonate, sodium
⊕ O- bonding in o-nitrophenol)
hydroxide, sodium metal are
N
Oδ - increasingly strong bases. Weak and strong
acids can be distinguished from each other
O δ⊕
δ⊕ ⊕ δ⊕ δ- H qulitatively by testing their reactivity
H δ⊕ N O-H O
O-H O towards bases of different strengths. A
δ- - H
δ⊕ weak acid does not react with a weak
(intermolecular hydrogen bonding in p-nitrophenol base, it requires a stronger base instead.
and water) Hence phenols react with NaOH but not
p-Nitrophenol has strong intermolecular with NaHCO3. A strong acid shows high
hydrogen bonding with solvent water. On reactivity towards weak as well as strong
the other hand, o-nitrophenol has strong base. For example : HCl is a strong acid.
intramolecular hydrogen bonding and Its reacts with both NaHCO3 and NaOH as
therefore the intermolecular attraction shown below:
towards solvent water is weak. The stronger
HCl(aq)+NaHCO3(aq)
the intermolecular attraction between solute
and solvent higher is the solubility. Hence H2O(l)+ NaCl(aq)+ CO2↑
p-nitrophenol has higher solubility in water HCl(aq)+NaOH(aq) NaCl(aq)+H2O(l)
than that of o-nitrophenol.
11.4.4 Chemical properties of Alcohols and • Alcohols show no acidic character in
Phenols aqueous solution, thus, alcohols do
not react with either aqueous NaHCO3
a. Laboratory tests of alcohols and phenols :
or aqueous NaOH. Very weak acidic
i. Litmus test : Water soluble alcohols and character of alcohol is revealed in the
phenols can be tested with litmus paper. reaction with active metal. When alcohols
Aqueous solution of alcohols is neutral to are treated with very strong base like alkali
litmus (neither blue nor red litmus change metal Na or K they react to give sodium
colour). Aqueous solutions of phenols turn or potassium alkoxide with liberation of
blue litmus red. Thus, phenols have acidic hydrogen gas.
character.
2R - OH + 2Na 2R-O Na⊕ + H2↑
ii. Reaction with bases :
Liberation of H2 gas is used to detect the
• Acid strength of phenols being very low, presence of alcoholic -OH group in a molecule.
phenols cannot react with NaHCO3 but
iii. Characteristic test for phenols : Phenols
react with NaOH.
reacts with neutral ferric chloride solution to
Ar - OH + NaHCO3(aq) No reaction give deep (purple/violet/green) colouration of
Phenols dissolve in aqueous NaOH by forming ferric phenoxide.
water soluble sodium phenoxide and are 3Ar - OH + FeCl3 (Ar -O)3 Fe + 3HCl
reprecipitated/regenerated on acidification (deep colour)
(neutral)
with HCl.
242
iv. Distinguishing test for alcohols (Lucas Electron donating inductive effect (+I effect) of
test) : Primary, secondary and tertiary alkyl group destabilizes the alkoxide ion (the
alcohols can be distinguished from each other conjugate base of alcohol). As a result alcohol
in the laboratory using Lucas reagent (conc. does not ionize much in water, and behaves
HCl and ZnCl2). The reaction involved is : like neutral compound in aqueous medium.
R - OH
HCl
R - Cl • Ionization of phenol is represented by the
ZnCl2
equilibrium shown in Fig. 11.1.
Alcohols are soluble in Lucas reagent but
the product alkyl chloride is not. Hence, the
clear solution becomes turbid when product O-H O
starts forming. Tertiary alcohols reacts fast
+ H2O + H3O⊕
and the reagent turns turbid instantaneously.
Secondary alcohols turn the reagent turbid (phenoxide)
Phenol
slowly. Primary alcohols turn the reagent
turbid only on heating. O O O
b. Reactions due to breaking of O -H bond.
i. Acidic character of alcohols and phenols :
I II III
From the laboratory tests it is
understood that in aqueous medium phenols O O
show weak acidic character while alcohols are
neutral. It is clear, therefore, that the reactivity
of alcohols and phenols towards ionization IV V
of O-H bond in them is different. The reason
behind this difference lies in the extent of Fig. 11.1 Ionization of phenol and resonance
stabilization of their respective conjugate stabilization phenoxide ion
bases by electronic effects as shown below. Phenoxide ion, the conjugate base of
• Ionization of alcohols is represented by the phenol, is resonace stabilized by delocalization
following equilibrium of the negative charge.Therefore phenol ionizes
in aqueous medium to a moderate extent, and
R - OH + H2O R O + H3O⊕ thereby shows a weak acidic character.
(alcohol) (alkoxide)

Problem 11.5 : Arrange the following compounds in decreasing order of acid strength and
justify.

i. CH3-CH2-OH ii. (CH3)3C-OH

iii. C6H5-OH iv. p-NO2-C6H4-OH

Solution : Compounds (iii) and (iv) are phenols and therefore are more acidic than the alcohols
(i) and (ii). The acidic strenghts of compounds depend upon stabilization of the corresponding
conjugate bases. Hence let us compare electronic effects in the conjugate bases of these
compounds :
Alcohols : H3C
C O (Conjugate base of (ii))
CH3 CH2 O (Conjugate base of (i)) and H3C
H3C

243
 The conjugate base of the alcohol (i) is destabilized by +I effect of one alkyl group,
where as conjugate base of the alcohol (ii) is destabilized by +I effect of three alkyl groups.
Hence (ii) is weaker acid than (i)

O O O O O O

N N N N N N
O ⊕ O O ⊕ O O ⊕ O O ⊕ O O ⊕ O O ⊕ O
I II III IV V VI

Phenols : The conjugate base of p-nitrophenol (iv) is better resonance stabilized due to six
resonance structures compared to the five resonance structures of conjugate base of phenol (iii)
(see Fig. 11.1). The resonance structure VI has -ve charge on only electronegative oxygens.
Hence the phenol (iv) is stronger acid than (iii). Thus the decreasing order of acid strength is
(iv) > (iii) > (i) > (ii)

Use your brain power O O

H⊕
R-OH + HO-C -R' R-O-C -R' + H2O
What are the electronic effects (alcohol) (acid) (ester)
exerted by -OCH3 and -Cl ? predict O O
the acid strength of H3C-O- -OH and H⊕
Ar-OH + HO-C -R' Ar-O-C -R' + H2O
Cl - -OH relative to parent phenol (phenol) (acid) (ester)
-OH .
Alcohols and phenols react with acid
anhydrides in presence of acid catalyst to form
ii. Esterification : Alcohols and phenols form
ester.
esters by reaction with carboxylic acid, acid
halides and acid anhydrides. The reaction O O O
H⊕
between alcohol or phenol with a carboxylic R-OH+R'-C -O-C -R' R-C -OR'+R'-COOH
acid to form an ester is called esterification. (alcohol) (anhydride) (ester) (acid)

Esterification of alcohol or phenol is carried O O O

H⊕
out in the presence of concentrated sulphuric Ar-OH+R'-C -O-C -R' Ar-O-C -R'+R'-COOH
acid. The reaction is reversible and can be (phenol) (anhydride) (ester) (acid)
shifted in the forward direction by removing
water as soon as it is formed.

244
The reaction of alcohol and phenols with ii. Reaction with phosphorous halide :
acid chloride is carried out in the presence of Alcohols react with phosphorous pentachloride
pyridine (base), which neutralizes HCl. (PCl5) and phosphorous trihalide (PX3) to form
O O alkyl halides. (refer to Chapter 10 section
pyridine
R-OH + Cl-C -R' R'-C -OR + HCl 10.3.1).
(alcohol) (acid chloride) (ester) iii. Dehydration of alcohols to alkenes :
O O Alcohol when treated with concentrated
pyridine
Ar-OH+ Cl-C -R' R'-C -O-Ar + HCl sulphuric acid or phosphoric acid or alumina
(phenol) (acid chloride) (ester) undergoes dehydration to form alkene and
water. (refer to Std. XI Chemistry Textbook
Acetyl derivatives : The CH3-CO- group section 15.2) The reaction gives more
is called acetyl group. The acetate esters of substituted alkene as the major product, in
alcohols or phenols are also called ‘acetyl accordance with Saytzeff rule.
derivatives’ of alcohols or phenols respetively.
The number of alcoholic or phenolic -OH
groups in the given compound can be deduced
from the number of acetyl groups introduced Problem 11.6 : Write the reaction showing
in it as a result of acetylation. Aspirin, a major and minor products formed on heating
well known generic medicine, is an acetyl butan-2-ol with concentrated sulfuric acid.
derivative of salicylic acid formed by its Solution : In the reaction described
acetylation using acetic anhydride. butan-2-ol undergoes dehydration to give
but-2-ene (major) and but-1-ene (minor) in
COOH accordance with Saytzeff rule.
OH O O
H⊕ OH CH3-CH=CH-CH3
+ CH3-C -O-C -CH3
CH3-CH -CH2-CH3Conc H2SO4 But-2-ene (major)
∆
(Salicylic acid) (Acetic anhydride) (Butan-2-ol) -H2O
CH2=CH-CH2-CH3
COOH But-1-ene (minor)
O
-O-C -CH3 + CH3COOH
(Acetic acid)
Do you know ?
(Aspirin/
Acetyl salicyclic acid) According to the common accepted
mechanism dehydration involves
c. Reaction due to breaking of C-O bond in
following three steps.
alcohols : ⊕
1. Formation of protonated alcohols R-OH2
i. Reaction with hydrogen halides :
Alcohols reacts with hydrogen halides to form 2. Its slow dissociation into carbocation
alkylhalides (refer to Chapter 10 section 10.3.1) 3. Fast removal of hydrogen ion to form
In general, tertiary alcohols react rapidly with alkene.
hydrogen halides; secondary alcohols react
⊕ -H2O -H⊕
somewhat slower; and primary alcohols, -C -C- H -C - C- -C -C - -C = C-
fast slow ⊕ fast
even more slowly. The order of reactivity of H OH H ⊕OH2 H
hydrogen halides is
(Alcohol) (Protonated (Carbocation) (Alkene)
HI > HBr > HCl alcohol)
HCl reacts only in the presence of anhydrous
ZnCl2. No catalyst is required in the case of
HBr and HI.

245
 O
Problem 11.7 : Write and explain reactions KMnO4/K2Cr2O7 (O)
R-CH2-OH HNO3(O)
[R-CHO] R-C -OH
to convert propan-1-ol into propan-2-ol ? (10 alcohol) (aldehyde) (carboxylic
Solution : The dehydration of propane-1-ol acid)
to propene is the first step. Markownikoff
hydration of propene is the second step to Tertiary alcohols are difficult to oxidise.
get the product propan-2-ol. This is brought On oxidation with strong oxidising agents at
about by reaction with concentrated H2SO4 high temperature tertiary alcohol undergoes
followed by hydrolysis. breaking of C-C bonds and gives a mixture
Al2O3
of carboxylic acids containing less number of
CH3-CH2-CH2-OH 623K
CH3-CH=CH2 carbon atoms than the starting 3° alcohol.
(Propan-1-ol) (Propene) Heating with Cu : When vapours of various
i. Con H SO
CH3-CH=CH2 ii. H O 2 4 CH3-CH -CH3 types of alcohols are passed over hot copper
2
OH the following reactions are observed.
(Propan-2-ol)
Cu/573K
R-CH2-OH Oxidation
R-CHO
iv. Oxidation of alcohols : (10 alcohol) (aldehyde)

Can you recall ? Cu/573K

R-CH -R' Oxidation R-C -R'
What are the various definitions of OH O
oxidation ? (2 alcohol)
0
(ketone)
Cu/573K
On reaction with oxidising agent H3C- C(OH) -CH3 dehydration
H3C- C = CH2
primary and secondary alcohols undergo CH3 CH3
dehydrogenation to form carbonyl compounds, (3 alcohol)
0
(alkene)
namely aldehydes and ketones respectively
Primary alcohol on oxidation with CrO3
forms aldehyde. However, a better reagent to Problem 11.8 : An organic compound
bring about this oxidation is PCC (pyridinium gives hydrogen on reaction with sodium
chlorochromate). metal. It forms an aldehyde having
PCC molecular formula C2H4O on oxidation
R-CH2-OH R-CHO
(O) with pyridinium chlorochromate Name the
(1 alcohol)
0
(aldehyde)
compounds and give equations of these
Seondary alcohol on oxidation with reactions.
chromic anhydride (CrO3) forms ketone.
CrO3
Solution : The given molecular formula
R-CH -R' (O) R-C -R' C2H4O of aldehyde is written as
OH O CH3 -CHO. Hence the formula
(20alcohol) (ketone)
of alcohol from which this is
When common oxidizing agents like
obtained by oxidation must be
nitric acid, potassium permanganate or
CH3-CH2-OH. The two reactions can,
potassium dichromate are used to oxidise
therefore, be represented as follows.
primary alcohol, the oxidation does not stop
at aldehyde stage, but the aldehyde formed is 2CH3-CH2-OH 2Na 2CH3-CH2O Na⊕+ H2
further oxidized to carboxylic acid containing (Ethyl alcohol) (Sodium ethoxide)
the same number of carbon atoms. [O]
CH3-CH2-OH CH3-CHO + H2O
PCC
(Ethyl alcohol) (Acetaldehyde)

246
d. Reactions of phenols : Phenol undergoes OH
electrophilic substitution reactions more readily HO-SO3H SO3H
as compared to benzene. The -OH group in 293K

phenol is ring activating and an ortho-/para- OH

(o- Phenolsulfonic acid)
directing group.
+ OH
i. Halogentaion of phenol: Phenol reacts
with aqueous solution of bromine to give (Phenol) HO-SO3H
2,4,6 -tribromophenol (chlorine reacts in the 373K
same way.) SO3H
OH (p- Phenolsulfonic acid)
OH
Br Br iv. Reimer-Tiemann Reaction : When phenol
H2O
+ 3Br2 + 3HBr is treated with chloroform in aqueous sodium
Br hydroxide solution followed by hydrolysis with
(Phenol) (2,4,6-tribromophenol) acid, salicylaldehyde is formed. This reaction
is known as Reimer-Tiemann reaction.
If the reaction is carried out in a solvent of
⊕
lower polarity than water, such as CHCl3, OH ONa
CCl4 or CS2, a mixture of ortho- and para- CHCl2
CHCl3 NaOH
bromophenol is formed.
aq. NaOH
OH OH OH (Phenol) Intermediate
Br ⊕
+ Br2 CS2
+ + HBr ONa OH
Low
temperature CHO CHO
(Phenol) (o- bromophenol) Br H3O⊕
(p- bromophenol)
Major product (Salicyaldehyde)
ii. Nitration of phenol : Phenol reacts with
dilute nitric acid at low temperature to give If carbon tetrachloride is used in place of
mixture of ortho- and para-nitrophenol. chloroform, salicylic acid is formed.
OH OH OH v. Kolbe reaction : The treatment of sodium
NO2 phenoxide with carbon dioxide at 398 K under
+ HO-NO2 + pressure of 6 atm followed by acid- hydrolysis,
(Phenol) (o- nitrophenol)
salicylic acid (o-hydroxybenzoic acid) is
NO2
formed. This reaction is known as Kolbe’s
(p- nitrophenol)
reaction
Phenol reacts with concentrated nitric acid to
⊕
form 2, 4, 6-trinitrophenol (picric acid) ONa OH
OH OH COONa
398K
O2N NO2 + CO2 6 atm H 3O ⊕
+ 3HO-NO2 Conc. + 3H2O
H SO 2 4
(Sodium (Sodium
(Phenol) NO2 salicylate) OH
Phenoxide)
(picric acid) COOH
iii. Sulfonation of phenol : Phenol reacts with
concentrated sulfuric acid at room temperature (Salicylic acid)
to give o-phenolsulfonic acid and at 373K,
p-phenol sulfonic acid
247
 H2SO4/443K
Do you know ? C2H5OH -H2O
CH2= CH2
(ethanol) (ethene)
Sodium phenoxide is more reactive
than phenol towards electrophilic Symmetrical ethers can be obtained from
substitution. Hence it is able to react primary alcohols by this method. Use of higher
with a weak electrophile like CO2 at high temperature or 2°/3° alcohols gives alkene as
temperature and pressure in Kolbe reaction. the major product.

vi. Oxidation of phenol : Phenol on oxidation Do you know ?

with chromic anhydride or sodium dichromate Dehydration of alcohols to form
in presence of H2SO4 gives p-benzoquinone. ether is a SN2 reaction. Protonated
alcohol species undergoes a backside
CrO3(O)
OH O O attack by second molecule of alcohol in a
or Na2Cr2O7/H2SO4
slow step. Subsequent fast deprotonation
(Phenol) (p-Benzoquinone)
results in formation of ether.
⊕
i. Protonation : C H -O-H H⊕
Phenol oxidizes slowly giving a dark coloured 2 5
C2H5-O-H
mixture in presence of air. H
⊕
vii. Catalytic hydrogenation of phenol: ii. SN2: C2H5- O
H + CH2-O-H -H2O
Phenol on catalytic hydrogenation gives H3C H
cyclohexanol. In this reaction a mixture of ⊕
vapours of phenol and hydrogen is passed over C2H5-O-CH2-CH3
nickel catalyst at 433 K. H
⊕
iii. Deprotonation : C H -O-C H
OH OH 2 5 2 5 -H⊕
H C2H5-O-C2H5
Ni
+ 3H2 433 K
(Phenol) (Cyclohexanol) b. Williamson Synthesis : Simple as well as
mixed ethers can be prepared in laboratory
viii. Reduction of phenol : Phenol is reduced by Williamson Synthesis. In this method
to benzene on heating with zinc dust. alkyl halide is treated with sodium alkoxide
OH or sodium phenoxide to give dialkyl ethers or
alkyl aryl ethers.
+ Zn + ZnO R-X + Na⊕ O -R R-O-R + NaX
(Phenol) (Benzene) R-X + Na⊕ O -Ar R-O-Ar + NaX
11.5 Ethers This reaction follows SN2 mechanism. Ether
is formed as a result of backside attack by
11.5.1 Preparation of ethers
alkoxide/ phenoxide ion (a nucleophile) on
a. Dehydration of alcohols : When alcohol is alkyl halide. The alkyl halide used in this
heated with dehydrating agent like concentrated reaction must be primary. For example : t-butyl
H2SO4 or H3PO4 two products, either an ether methyl ether can be synthesised by reaction of
or an alkene, can form depending upon the methyl bromide with sodium t-butoxide.
temperature. For example : dehydration of
ethanol by H2SO4 gives ethoxyethane at 413 (CH3)3C-O Na⊕ + CH3-Br
K, while ethene is formed at 443 K. (sodium t-butoxide) (methyl bromide)

2C2H5OH
H2SO4/413K
C2H5-O-C2H5 (CH3)3C-O-CH3 + NaBr
-H2O
(ethanol) (Ethoxyethane) (t-butyl methyl ether)

248
If secondary or tertiary alkyl halides are used,
C2H5-Cl + Na⊕O -CH-CH3 C2H5-O-CH-CH3
the reaction leads mainly to alkene formation
(Ethyl CH3 CH3
(elimination reaction). For example :
chloride) (Sodium (ethyl isopropyl
CH3
CH3
isopropoxide) ether)
CH3-C - Cl + Na⊕O -C2H5 CH3-C = CH2 + NaCl
CH3 (sodium ethoxide) (isobutene)
( t-butyl chloride) + C2H5OH + NaCl 11.5.2 Physical properties :
(ethanol)
a. Physical state and boiling points
Aryl halides do not give Williamson’s
synthesis. i. Dimethyl ether and ethyl methyl ether are
gases. Other ethers are colourless liquids with
Can you think ?
pleasant odour.
Williamson synthesis an effective
method for preparation of ethers ii. Lower ethers are highly volatile and highly
from hydroxy compounds. The inflammable substances.
substrates of Williamson synthesis, namely iii. Boiling points of ethers show gradual
the nucleophile and alkyl hadlides are increase with the increase in molecular mass.
obtained from hydroxy compounds as
shown below. Ether B.P. / K
OH ONa CH3-O-CH3 248
+ NaOH C2H5-O-CH3 284
Phenol (Phenoxide)
HX C2H5-O-C2H5 308
C2H5X (alkyl halide)
C2H5-OH Na b. Polarity and solubility : Since -C-O-C-
C2H5ONa (alkoxide)
bond angle is 110° and not 180°, the bond
dipole moments of the two C-O bonds donot
Problem 11.9 : Ethyl isopropyl ether does
cancel each other; therefore ethers posses a
not form on reaction of sodium ethoxide
small net dipole moment (For example, dipole
and isopropyl chloride.
moment of diethyl ether is 1.18 D)
C2H5-ONa + Cl-CH-CH3
CH3 R
× C2H5-O-CH-CH3 net dipole
CH3 110° O moment
R
i. What would be the main product of this
reaction ?
Weak polarity of ethers does not affect their
ii. Write another reaction suitable for the boiling points, which are about the same as
preparation of ethyl isopropyl ether. those of alkanes having comparable molecular
Solution : i. Isopropyl chloride is a mass. (see table 11.6).
secondary chloride. On treating with sodium Table 11.6 Comparative boiling points of
ethoxide it gives elimination reaction to alkane, ether and alcohol
form propene as the main product . Methyl
n-Hep- n-Hexyl
C2H5-ONa + Cl-CH-CH3 CH3-CH=CH2 Name n-pentyl
tane alcohol
CH3 (Propene) ether

(Sodium (isopropyl
ethoxide)

+ C2H5OH + NaCl Molecular
chloride) 100 102 102
(Ethyl alcohol) mass
ii. Ethyl isopropyl ether can be prepared
by using ethyl chloride (10chloride) as Boiling
371 373 430
substrate. point / K

249
The intermolecular hydrogen bonding that R-O-R + H-O-H
H 3O ⊕
2R-OH
∆
holds alcohol molecules together strongly, is ⊕
H
not present in ethers and alkanes. However, R-O-R' + H-O-H ∆ R-OH + R'-OH
solubility/miscibility of ethers in water is H⊕
Ar-O-R + H-O-H ∆ Ar-OH + R-OH
similar to that of alcohols of comparable
molecular mass. This is because ethers can ii. Reaction with PCl5 : Ethers react with PCl5
form hydrogen bonds with water through the to give alkyl chlorides
ethereal oxygen.
R-O-R' + PCl D R-Cl + R'-Cl + POCl
5 3
δ δ⊕
R- O H -O iii. Reaction with hot concentrated acid :
R H Alkyl ethers react with hot and concentrated
HI and HBr to give an alcohol and an alkyl
For example diethyl ether and n-butyl alcohol
halide.
have respective miscibilities of 7.5 and 9g per
100 g of water. R-O-R + HX R-X + R-OH
11.5.3 Chemical properties of ethers : R-OH HX R-X + H2O
a. Laboratory test for ethers : Ethers are The order of reactivity of HX is HI>HBr>HCl
neutral compounds in aqueous medium.
Ethers do not react with bases, cold dilute
Do you know ?
acids, reducing agents, oxidizing agents and
active metals. However, ethers dissolve in Mechanism of first stage : Reaction
cold concerntrated H2SO4 due to formation of of ether with hot concentrated
oxonium salts. HI involves formation of oxonium ion by
H protonation in the first step and subsequent
R-O-R' + H2SO4 R-O-R' HSO4 nucleophilic substitution reaction brought
⊕ about by the powerful nucleophile I . The
This property distinguishes ethers from least substituted carbon in oxoinium ion is
hydrocarbons. attacked by I following SN2 mechanism.
∆ ⊕
b. Reaction involving alkyl group of ether : CH3-O-CH2-CH3 + H-I CH3-O-CH2-CH3
i. Formation of peroxide : Ethers combine H
+ I
with atmospheric oxygen to form peroxide. 1 1
O-OH ⊕ 2 2
⊕
I CH3-O-CH2-CH3 I CH3 O-CH2-CH3
CH3-CH2-O-C2H5 + O2 Long CH3-CH-O-C2H5 H
contact H
(diethyl ether)
with air (peroxide of
(oxygen) diethyl ether)
CH3- I + CH3-CH2-OH
For example :
All ethers which have been exposed to • Use of excess HI converts the alcohol into
the atmosphere contain peroxide. This is very alkyl iodide.
undesirable reaction. Peroxides are hazardous • In case of ether having one tertiary alkyl
because they decompose violently at high group the reaction with hot HI follows SN1
temperature. mechanism, and tertiary iodide is formed
rather than tertiary alcohol.
c. Reactions involving C-O bond ⊕ slow
Step 1 : (CH3)3C-O-CH3 (CH3)3C⊕
i. Reaction with hot dilute sulphuric acid H
(Hydrolysis) : Ethers when heated with dilute

+ CH3OH
sulfuric acid under pressure undergo hydrolysis
to give alcohols/phenols. Step 2 : (CH3)3C⊕ + I fast (CH3)3C-I

250
Aryl alkyl ethers have stronger and shorter OCH3 OCH3 OCH3
bond between oxygen and the aromatic ring. CH3
Anhydrous
Hence an aryl alkyl ether undergoes cleavage + CH3Cl AlCl3 +
of oxygen - alkyl bond and yields a phenol
(Anisole) CH3
and an alkyl halide on reaction with HI.
(4-Methoxy (2-Methoxy
toluene) toluene)
CH3 (major) (minor)
O OH
OCH3 OCH3
+ HI 398K + CH3I
Anhydrous
(Anisole) (Phenol) (Methyl iodide) + CH3COCl AlCl3 +
(Anisole) COCH3
d. Electrophilic substitution in aromatic (4-Methoxy
ethers : The alkoxy group in aromatic acetophenone)
ether is a ring activating and ortho-, para- (major)
directing group toward electrophilic aromatic
OCH3
substitution. This is evident from the resonance
COCH3
structures:
⊕ R ⊕ ⊕ R
O
R
O O
R
O OR (2-Methoxy
acetophenone)
(minor)
iii. Nitration : Anisole reacts with concentrated
(I) (II) (III) (IV) (V) nitric acid in presence of concentrated sulfuric
acid (Nitrating mixture) to give a mixture of
+R Effect of -OR group results in increased o-nitro anisole and p-nitro anisole.
electron density at the para- and two ortho- OCH3 OCH3 OCH3
positions (see resonance structures II, III and conc HNO3 NO2
IV). +
conc H2SO4
i. Halogenation : Anisole undergoes (Anisole) NO2
bromination with bromine in acetic acid even (4-Nitroanisole) (2-Nitroanisole)
in the absence of ferric bromide catalyst. It (major) (minor)
is due to activation of benzene ring by the
methoxy group. 11.6 Uses of alcohols, phenols and ethers
OCH3 OCH3 OCH3 Alcohols :
Br2 Br 1. Methyl alcohol is used as a solvent for
CH3COOH +
paints and varnishes.
Br 2. Ethyl alcohol is used as antifreeze agent
(Anisole) (major) (minor) in automobile radiators. It is also used as
(p-bromo anisole) (o-bromo anisole) solvent.
ii. Friedel Crafts reaction : Anisole reacts Phenols :
with alkyl halide and acyl chloride in presence 1. Phenol is used in preparation of phenol
of anhydrous AlCl3 (Lewis acid) as catalyst. formaldehyde resin For example : bakelite.
2. Phenols are used as antiseptic in common
products like air freshners, deodarants,
mouthwash, calamine lotions, floor
cleaners, etc.
251
Ethers :
1. Earlier diethyl ether was used as a general anaesthetic in surgical operations.
2. Diethyl ether is used as a solvent for Grignard reagents, fats, waxes, oil, etc.

Exercises

1. Choose the correct option.

i. Which of the following represents the v. Resorcinol on distillation with zinc dust
increasing order of boiling points of (1), gives
(2) and (3)? A. Cyclohexane B. Benzene
(1) CH3-CH2-CH2-CH2-OH C. Toluene D. Benzene-1, 3-diol
(2) (CH3)2CH-O-CH3 vi. Anisole on heating with concerntrated HI
(3) (CH3)3COH gives

A. (1) < (2) < (3) B. (2) < (1) < (3) A. Iodobenzene

C. (3) < (2) < (1) D. (2) < (3) < (1) B. Phenol + Methanol

ii. Which is the best reagent for carrying out C. Phenol + Iodomethane
following conversion ? D. Iodobenzene + methanol
CH3 CH3
vii. Which of the following is the least acidic
OH compound ?
OH
OH
A. LiAlH4 B. Conc. H2SO4, H2O A. B.
C. H2/Pd D. B2H6, H2O2-NaOH
CH3
iii. Which of the following reaction will give
OH OH
ionic organic product on reaction ?
C. D.
A. CH3-CH2-OH + Na
B. CH3-CH2-OH + SOCl2 NO2
NO2
C. CH3-CH2-OH + PCl5
viii. The compound incapable of hydrogen
D. CH3-CH2-OH + H2SO4
bonding with water is ......
iv. Which is the most resistant alcohol
A. CH3-CH2-O-CH3
towards oxidation reaction among the
follwoing ? B. CH3-CH2-CH2-CH3
A. CH3-CH2-OH B. (CH3)2CH-OH OH
C. (CH3)3C-OH D. C2H5- CH -OH C.
CH3
D. CH3-CH2-CH2-OH

252
ix. Ethers are kept in air tight brown bottles 4. An ether (A), C5H12O, when heated
because with excess of hot HI produce two
alkyl halides which on hydrolysis form
A. Ethers absorb moisture
compound (B)and (C), oxidation of (B)
B. Ethers evaporate readily gave and acid (D), whereas oxidation
C. Ethers oxidise to explosive peroxide of (C) gave a ketone (E). Deduce the
structural formula of (A), (B), (C), (D)
D. Ethers are inert and (E).
x. Ethers reacts with cold and concentrated 5. Write structural formulae for
H2SO4 to form
a. 3-Methoxyhexane
A. oxonium salt B. alkene
b. Methyl vinyl ether
C. alkoxides D. alcohols
c. 1-Ethylcyclohexanol
2. Answer in one sentence/ word.
d. Pentane-1,4-diol
i. Hydroboration-oxidation of propene
gives..... e. Cyclohex-2-en-1-ol

ii. Write the IUPAC name of alcohol having 6. Write IUPAC names of the following
molecular formula C4H10O which is
HO CH3
resistant towards oxidation. i.
iii. Write structure of optically active alcohol
having molecular formula C4H10O
ii. CH3-CH -CH -CH2-OH
iv. Write name of the electrophile used in
OH CH3
Kolbe’s Reaction.
3. Answer in brief. O-CH3
OH
i. Why phenol is more acidic than ethyl iii. iv.
alcohol ? NO2
ii. Why p-nitrophenol is a stronger acid than
phenol ?
iii. Write two points of difference between Activity :
properties of phenol and ethyl alcohol.
iv. Give the reagents and conditions necessary • Collect information about
to prepare phenol from production of ethanol as byproduct
a. Chlorobenzene in sugar industry and its
importance in fuel economy.
b. Benzene sulfonic acid.
v. Give the equations of the reactions for • Collect information about phenols
the preparation of phenol from isopropyl used as antiseptics and polyphenols
benzene. having antioxidant activity.
vi. Give a simple chemical test to distinguish
between ethanol and ethyl bromide.

253