11.alcohol, Phenol & Ethers Colour Booklet PDF

Chapter – 2
Part – A : ALCOHOLS
1 INTRODUCTION
An alcohol is a compound produced by the replacement of one or more hydrogen atoms of an
aliphatic hydrocarbon by hydroxyl (– OH) group i.e., alcohols are the hydroxyl derivatives of
hydrocarbons.
 General formula : Alcohols are the hydroxyl derivatives of alkanes having general formula CnH2n + 1OH.

2 CLASSIFICATION OF ALCOHOLS

 The hydrocarbon part of an alcohol may be saturated or unsaturated & accordingly, alcohols may be
divided into two classes, viz., Saturated & Unsaturated.
Examples: CH3CH2CH2OH ⇒ 𝑛-propyl alcohol (saturated)
CH2 = CH – CH2OH ⇒ Allyl alcohol (unsaturated)
 Depending on whether the molecules contain one, two or three hydroxyl group(s), alcohols are
classified as monohydric, dihydric & trihydric. When four or more hydroxyl groups are present,
they are generally called polyhydric alcohols.
Examples: CH3CH2OH CH2 – OH CH2 – OH CH2 – OH
Ethyl alcohol CH2 – OH CH – OH (CHOH)4
[Monohydric alcohol] Ethylene glycol CH2 – OH CH2 – OH
[Dihydric alcohol] Glycerol Sorbitol
[Trihydric alcohol] [Polyhydric alcohol]
 Classification of monohydric alcohols
Monohydric alcohols are classified as Primary (10), Secondary (20) & Tertiary (30), depending upon
the nature of the carbon atom to which the hydroxyl group (– OH) is bonded.
1. Primary or 10 alcohols: They possess a characteristic (– CH2OH group).
The carbinol carbon is attached to at least two H – atoms.
R – CH2OH H – CH2OH CH3 – CH2OH
Primary alcohol Methanol Ethanol
Here, R = H or alkyl group
2. Secondary or 20 alcohols: They possess a characteristic ( CHOH group).
The carbinol carbon is attached to at least one H – atoms.
R H3C CH3CH2
CH2OH CHOH CHOH
R H3C H3C
Secondary alcohol Isopropyl alcohol sec – butyl alcohol
(Propan-2-ol or, 2-Propanol) (butan-2-ol or 2-Butanol)
Here, R = alkyl group
3. Tertiary or 30 alcohols: They possess a characteristic ( CHOH group).
The carbinol carbon is not attached to any H – atoms.
R CH3 CH3
R – C – OH CH3 – C – OH CH3CH2CH2 – C – OH
R CH3 CH3
Tertiary alcohol tert-butyl alcohol 2-Methylpentan-2-ol
(2-Methylpropan-2-ol)
Here, R = alkyl group
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3 NOMENCLATURE OF ALCOHOLS
There are three systems for naming the alcohols:
 Common System: In this system, alcohols (R – OH) are named as alkyl alcohols, i.e., the word
alcohol is added to the name of alkyl group. In higher members, it is always indicated whether the
(– OH) group is attached to primary, secondary or tertiary carbon atom by prefixing ‘n’ for primary,
‘sec’ for secondary & ‘tert’ for tertiary.
CH3OH ; CH3CH2OH ;
Methyl alcohol Ethyl alcohol
OH
CH3CH2CH2OH ; CH3 – CH – CH3 ;
n-Propyl alcohol Isopropyl alcohol
OH
CH3CH2CH2CH2OH ; CH3 – CH2 – CH – CH3 ;
n-Butyl alcohol sec-Butyl alcohol
OH
CH3 – CH – CH2OH ; CH3 – CH – CH3 ;
CH3 CH3
Isobutyl alcohol tert-Butyl alcohol
 Carbinol System: The simplest monohydric alcohol, CH3OH, is called carbinol. All other members
are considered its alkyl derivatives. The alkyl groups attached to the carbon atom carrying (– OH )
group are named in alphabetical order.
CH3OH ; CH3CH2OH ; CH3 CH3 CH3
Carbinol Methyl alcohol CHOH ; C2H5 – C – OH ; CHCH2OH
CH3 H CH3
Dimethyl carbinol Ethyl methyl carbinol Isopropyl carbinol
CH3 C2H5
CH3 – OH ; C2H5 – C – OH
CH3 C2H5
Trimethyl carbinol Triethyl carbinol
 IUPAC System: According to this system, the alcohols are called alkanols, i.e., by replacing (–e) from
the name of alkane by (–ol), i.e., Alkane (–e) + ol = Alkanol.
The IUPAC names of a few other alcohols below:
5
CH3 C2H5
4 3 2 1 1 2 3
CH3 – C – CH – CH3 ; CH3 – CH – CH – CH3
H3C OH OH
3, 3-Dimethylbutan-2-ol 3-Methylpentan-2-ol
Br Br
ClCH2CH2 – CHCH2OH ; CH3 – C – CH – CH2OH
CH3 CH3
4-Chloro-2-methylbutan-1-ol 2, 3-Dibromo-3-methylbutan-1-ol
CH2 = CH – CH – CH3 ; CH ≡ C – CH2OH
OH Prop-2-yn-1-ol (Propargyl alcohol)
But-3-en-2-ol

C6H5 CH2OH
CH3 – CH2 – C – CH2CH3 ;
OH
3-Phenylpentan-3-ol Cyclohexylmethanol
CH2 = CH – CH2OH ; CH3 – CH – CH2Cl
Prop-2-en-1-ol OH
(Allyl alcohol) 1-Chloropropan-2-ol
CH3 – CHOH – CH2OH ; OH – CH2CH2CH2 – OH
Propane-1, 2-diol Propane-1, 3-diol
CH3
CH3 – C – OH OH CH3
OH
; ; Br
Br
2-Phenylpropan-2-ol 1-(2’-Bromo phenyl)-2- 1-Bromo-1-phenylethanol
methylpropan-1-ol
 The common & IUPAC names of some monohydric alcohols are listed given beside column.
Formula Of Alcohol Common Name IUPAC Name

CH3OH Methyl alcohol Methanol
CH3CH2OH Ethyl alcohol Ethanol
CH3CH2CH2OH n-Propyl alcohol Propan-1-ol
CH3 – CH – CH3 Isopropyl alcohol Propan-2-ol
OH
CH3CH2CH2CH2CH3 n-Butyl alcohol Butan-1-ol
CH3 – CH – CH2CH3 sec-Butyl alcohol Butan-2-ol
OH
CH3 – CH – CH2OH Isobutyl alcohol 2-Methylpropan-1-ol
CH3
CH3
CH3 – C – CH3 tert-Butyl alcohol 2-Methylpropan-2-ol
OH
CH3CH2CH2CH2CH2OH n-Pentyl alcohol Pentan-1-ol
CH3 – CH – CH2CH2OH Isopentyl alcohol or, 3-Methylbutan-1-ol
CH3 Isoamyl alcohol
CH3 tert-Pentyl alcohol 2-Methylbutan-2-ol
CH3 – C – CH2CH3 or,
OH tert-Amyl alcohol
CH3 Neopentyl alcohol 2, 2-Dimethylpropan-1-ol
CH3 – C – CH2OH or,
CH3 Neoamyl alcohol

4 ISOMERISM IN ALCOHOLS
Monohydric saturated alcohols show the following three types of isomers:
a) Chain isomerism: Alcohols containing four or more carbon atoms exhibit chain isomerism in which
the isomers differ in the chain of carbon atoms attached to the hydroxyl group.
Examples: CH3CH2CH2CH2OH & CH3CHCH2OH (C4H10O)
Butan-1-ol CH3
(n-Butyl alcohol) 2-Methylpropan-1-ol
(Isobutyl alcohol)
b) Position isomerism: Alcohols containing three or more carbon atoms show position isomerism in
which the isomers differ in the position of hydroxyl group when carbon chain is the same.
Examples: CH3CH2CH2OH & CH3 – CH – CH3 (C3H8O)
Propan-1-ol OH
(n-Propyl alcohol) Propan-2-ol
(Isopropyl alcohol)
CH3CH2CH2CH2OH & CH3 – CHCH2CH3 (C4H10O)
Butan-1-ol CH3
(n-Butyl alcohol) Butan-1-ol
(sec-Butyl alcohol)
c) Functional isomerism: Saturated monohydric alcohols containing two or more carbon atoms show
functional isomerism with ethers. Both have the same general formula C nH2n + 2O.
Examples: CH3CH2OH & CH3 – O – CH3 (C2H6O)
Ethanol Methoxymethane
(Ethyl alcohol) (Dimethyl ether)
CH3CH2CH2OH & C2H5 – O – CH3 (C3H8O)
Propan-1-ol Methoxyethane
(n-Propyl alcohol) (Ethyl methyl ether)
Besides the structural isomerism, alcohols having asymmetric carbon atom exhibit optical isomerism
(enantiomerism) also.
Examples: H Asymmetric C-atom
Butan – 2 – ol ; CH3 – C – OH
(sec – Butyl alcohol) C2H5
H Asymmetric C-atom
Pentan – 2 – ol ; CH3 – C – OH
(sec – Amyl alcohol) C3H7
5 STRUCTURE OF ALCOHOLS
 The general formula of alcohols is R – OH, where R is some alkyl or substituted alkyl group & the –
OH group in alcohols is attached to sp2 – hybridised carbon of – CH3 by a sigma (𝜎) bond formed by
the overlap of sp3 – hybrid orbital of oxygen.
 The C – O –H bond angle in alcohols is slightly less than the regular tetrahedral angle (109028’). It is
due to greater repulsion of loan pairs of oxygen on the bond pair.
 The oxygen atom is more electronegative than both carbon & hydrogen, the electrons of C – O & the
O – H bonds are a little more displaced towards the oxygen atom. As a result, the oxygen has partial
negative charge (𝛿 −) & carbon & hydrogen each have a partial positive charge (𝛿 +) & so alcohols
possess a net dipole moment.
 The C – O bond length in alcohols is 142 pm.
 The structure of the simplest alcohol is:
H
H C O
H H
108.50

Illustration: 1. (a) Classify the following as primary, secondary & tertiary alcohols:
(b) Identify allylic & benzylic alcohols in the given followings:
CH3
(i) CH3 – C – CH3OH (ii) H2C = CH – CH2OH (iii) CH3 – CH2 – CH2OH
CH3
OH OH CH3
CH – CH2 CH2 – CH – CH3 CH = CH – C – OH
(iv) (v) (vi) CH3
Solution: (a) Alcohols (i), (ii) & (iii) are primary.

Alcohols (iv) & (v)
Alcohol (vi) is tertiary.
(b) Alcohols (ii) & (iv) are allylic.
Alcohol (iv) is benzylic.
Illustration: 2. Write structures & IUPAC names of all the isomeric alcohols having molecular formula
C5H11OH which can exhibit enantiomerism.
Solution: There are three isomeric alcohols having molecular formula C5H11OH which can exhibit
enantiomerism.
(a) CH3CH2CHCHCH3 (b) CH3CHCHCH3 (c) CH3CH2CHCH2OH
H3C OH CH3
Pentan-2-ol 3-Methylbutan-2-ol 2-Methylbutan-1-ol
Illustration: 3. Write the structures & names of all the cyclic C 4H7OH isomers. Indicate any chirality.
Solution: (a) H (b) CH2OH (c) CH3
OH H OH
Cyclobutanol Cyclopropyl methanol 1-Methylcyclopropanol
(d) CH3 OH (e) H OH

H H CH3 H
2-Methylcyclopropanol 2-Methylcyclopropanol
(cis –) , chiral (trans –) , chiral
Illustration: 4. Write the structural formula & give IUPAC names for all isomeric alcohols of the molecular
formula C4H10O.
Solution: C4H10O is a monohydric alcohol, i.e., C4H9OH. It can have four isomeric alcohols.
CH3CH2CH2CH2OH & CH3 OH CH3
Butan-1-ol CH3 – CH – CH2OH CH3CH2 – CH – CH3 & CH3 – C – CH3
2-Methylpropan-1-ol Butan-2-ol OH
are primary alcohol (sec-Alcohol) 2-Methylpropan-2-ol
(tert-Alcohol)
Illustration: 5. What type of isomerism does exist between the following pairs of compounds:
(a) Pentan-1-ol & Pentan-2-ol ;
(b) Pentan-1-ol & 3-Methylnutan-1-ol
(c) Butan-1-ol & Diethylether
Solution: (a) Position isomerism ;
(b) Chain isomerism ;
(c) Functional isomerism

6 METHODS OF PREPARATION OF ALCOHOLS

Acid Catalysed Hydration H2O
H2C = CH2 + H2SO4 C2H5 – HSO4 CH3CH2OH
Ethene Ethyl hydrogen sulphate Ethanol
Oxymercuration Demercuration Hg(OAc)2

CH3CH2CH = CH2 CH3CH2CH – CH2
From
Alkenes THF/– H2O OH HgOCOCH3
CH3CH2CH – CH3 NaBH4
OH HO –
Butan-2-ol
By Hydroboration Oxidation
CH3CH = CH2 + (H – BH2)2 CH3CH2CH2BH2 CH3CH = CH2
Diborane n-Propyl borane
(CH3CH2CH2)2BH
di-n-Propyl borane
H2O2 CH3CH = CH2
H3BO3 + 3CH3CH2CH2OH (CH3CH2CH2)3B
OH–/H2O
tri-n-Propyl borane
By Grignard Reagent CH3MgBr H2O/H+

From H2C = O CH3CH2OMgBr C2H5OH + Mg(OH)Br
Aldehydes Formaldehyde Ethanol Hydroxy
& Ketones Magnesium
Bromide
By Reduction LiAlH4
CH3CHO + 2H CH3CH2OH
O
By Reduction LiAlH4
CH3 – C – OCH2CH3 + 4[H] 2CH3CH2OH
From Ethyl ethanoate Ethanol
Esters
O OMgBr
By Grignard Reagent CH3MgBr – C2H5OMgBr
CH3 – C – OC2H5 CH3 – C – OC2H5
Ethyl ethanoate
CH3
O
CH3 – C – CH3
OH OMgBr
H2O/H+ CH3MgBr
Mg(OH)Br + CH3 – C – CH3 CH3 – C – CH3
Hydroxy
Magnesium CH3 CH3
Bromide 2-Methyl propan-2-ol
By Hydrolysis
C2H5Br + AgOH C2H5OH + AgBr
of Haloalkanes Bromoethane Moist Silver Ethanol
H2O/H+
From Ethylene RMgX + CH2 – CH2 RCH2CH2OMgX RCH2CH2OH + MgX(OH)
Oxide
O
Ethylene oxide
(Oxirane)

Illustration: 1. Write structures of the products of the following reactions:

2 H O/H+
(i) CH3 – CH = CH2
O
CH2 – C – OCH3
(ii) O NaBH4
(iii) CH3 – CH2 – CH – CHO NaBH4

CH3
Solution: (i) CH3 – CH – CH3
OH
OH
CH2 – C – OCH3
(ii) O
(iii) CH3 – CH2 – CH – CH2OH

CH3
Illustration: 2. Complete the following equations:
H2O/H+
(i) (CH3)2C = O RMgX ? ?
[CO + H2]
(ii) ? ? LiAlH4 CH3CH2CH2OH
[Co(CO)4]2
Solution:(i) CH3 – CH2 – CH2 – CH2 – OH

(Butan – 1 – ol)
CH3
(ii) CH3 – CH – CH3 (iii) CH3 – C – OH
OH CH3
(Propan – 2 – ol) (2-Methylpropan – 2 – ol)
Illustration: 3. Complete the following equations:
(i) CH3CH2CH2COOH ? CH3CH2CH2CH2OH
(ii) CH3
C = O + CH3CH2MgI ? ?
CH3 H2O
(iii) CH3CH2COOC2H5 + 2CH3MgI ? ?
? MnO2
(iv) CH.COOC2H5 CHCH2OH
? BrCH2CH2CH2OH
(v) BrCH2CH2COCl ?
CH3CH2CH2OH
LiAlH4 or B2H6
Solution: (i) CH3CH2CH2COOH 4[H] / – H2O
CH3CH2CH2CH2OH
(ii) CH3 CH3 OMgI CH3 OH
H+
C = O + CH3CH2MgI C C
CH3 CH3 CH2CH3 CH3 CH2CH3
OMgI
CH3MgI
(iii) CH3CH2COOC2H5 + 2CH3MgI CH3CH2 – C – OC2H5 – MgIOC2H5
CH3
OMgI OH
H2O
CH3CH2 – C – CH3 CH3CH2 – C – CH3
CH3 CH3

LiAlH4 MnO2
(iv) CH.COOC2H5 CHCH2OH
CH.CHO
LiAlH4 LiAlH4
(v) CH3CH2CH2OH BrCH2CH2COCl AlCl3 BrCH2CH2CH2OH
Illustration: 4. Write the products name of the following reactions:

(i) O
Na/C2H5OH
CH3 – C – OCH3 Heat (A) + (B)
O
(i) LiAlH4 / ether
(ii) CH3CH2 – C – OC2H5 (ii) H3O+ (A) + (B)
O
LiAlH4
(iii) R – C – Cl Or, NaBH4 / Ethanol (A)
Or, H2 / Ni
H2O2
(iv) 3CH3 CH = CH2 B2H6 (A) (B) + (C)
NaOH
(v) R – CH = CH2 + Hg(OCOCH3)2 H2O (A) NaBH4 (B) + (C) + (D)

THF NaOH
Solution: (i) O
Na/C2H5OH
CH3 – C – OCH3 Heat CH3CH2OH + CH3OH
Ethanol Methanol
O
(i) LiAlH4 / ether
(ii) CH3CH2 – C – OC2H5 (ii) H3O+ CH3CH2CH2OH + C2H5OH
Propan – 1 – ol Ethanol
O
LiAlH4
(iii) R – C – Cl Or, NaBH4 / Ethanol RCH2OH
10 alcohol
Or, H2 / Ni
B2H6 H2O2
(iv) 3CH3 CH = CH2 (CH3CH2CH2 – )3B NaOH
BO3𝛩
3 + 3CH3CH2CH2OH
10 alcohol
NaBH4
(v) R – CH = CH2 + Hg(OCOCH3)2 H2O R – CH – CH2 – HgOCOCH3 NaOH
THF
OH
Hydroxymercuric salt
Hg + CH3COONa + R – CH – CH3
OH
20 alcohol
Illustration: 5. What is Bouveault-Blanc reduction?
Solution: Esters, on being heated with sodium & ethanol, are reduced & two molecules of alcohol
(same or different type) are produced.
The alcohol produced from the acyl part of the ester (RCO – ) is always found to be primary
alcohol. But the alcohol produced from the alkoxy ( – OR’) part may be 10 , 20 or 30.
The reduction of an ester by Na & ethanol is known as Bouveault-Blanc reduction.
(The reduction of aldehyde & ketone by Na / C2H5OH is also known by the same name).
Na / C2H5OH
R – C – OR’ RCH2OH + R’OH
Heat
O 10 alcohol 10 alcohol

7 PROPERTIES OF ALCOHOLS
 Physical Properties of Alcohol:
a) Nature: At ordinary temperature, lower members of alcohols are colourless, volatile, neutral liquids with
characteristic alcoholic smell & burning taste. Higher alcohols are colourless, odourless, neutral solids.
b) Solubility: Lower alcohols are higher than water & completely miscible in water but the solubility
progressively decreases with the increase in relative molecular masses (molecular weight). Higher alcohols
are odourless, waxy solids & insoluble in water.
Among the isomeric alcohols, solubility in water increases with increase in number of branches in the
carbon chain.
c) Boiling points: Boiling points of alcohols belonging to the same class increase with the increase in their
molecular weights. For isomeric alcohols having same molecular formula, boiling points show following
trend: Primary > Secondary > Tertiary.
In polyhydric alcohols, the degree of molecular association through hydrogen bonding increases as the
viscosity & boiling point increase. For example:
CH2OC2H5 CH2OC2H5 CH2OH
CHOC2H5 CHOH CHOH
CH2OH CH2OH CH2OH
Diethyl glycerol Monoethyl glycerol Glycerol
(boiling point 1900C) (boiling point 2300C) (boiling point 2900C)
d) Effect on human body: Lower alcohols have adverse effects on human body. Methyl alcohol is poisonous &
it affects optic nerve leading to blindness. Ethyl alcohol agitates central nervous system, in consequence
body becomes insensitive & temperature falls gradually.
Illustration: 1. Explain why tert-Butyl alcohol is much more soluble in water than n-Butyl alcohol.
Solution: In tert-butyl alcohol, alkyl group is highly branched & hence approaches almost spherical shape.
As a result non-polar part of the molecule becomes less prominent & hence it can have stronger
intermolecular H-bonds with water molecules through its O – H group. On the other hand
n-butyl alcohol has predominantly non-polar character.
Illustration: 2. Arrange the following compounds in increasing order of their boiling point:
(i) CH3CH2OH (ii) HOCH2CH2OH (iii) CH3CH2Cl
Solution: Alcohols have higher boiling points than alkyl halides due to intermolecular hydrogen bonding.
Moreover, dihydric alcohols have greater extent of hydrogen bonding than monohydric alcohols
due to the presence of two hydroxyl groups, therefore, the boiling point of HOCH 2 CH2OH is
higher than that of CH3CH2OH while that of CH3CH2Cl is lowest due to absence of H-bonding.
Hence, the boiling points of the above given compounds increase in the order:
CH3CH2Cl < CH3CH2OH < HOCH2CH2OH.
Illustration: 3. Explain why ethanol boils at higher temperature than the corresponding alkane.
Solution: Ethanol (C2H5OH) contains O – H bond due to which intermolecular H-bonding is possible in it.
........... O – H ........... O – H ........... O – H .............
C2H5 C2H5 C2H5
As a result, ethanol has higher boiling point than ethane which has weak van der Waal’s forces
as intermolecular forces.
Illustration: 4. Explain why n-Hexanol is not soluble in water.
Solution: In n-hexanol, alkyl group is quite large. As a result it resembles the hydrocarbons more closely
& is not soluble in water. The extent of H-bonding between n-hexanol & water is very less.
Illustration: 5. What do you mean by intoxicating effect? What is its uses?
Solution: Alcohols are known to have intoxicating effect. Methanol is poisonous & is not good for drinking
purposes. It causes blindness. Ethanol, on the other hand, is used for drinking purposes. Sometimes it is
rendered undrinkable by adding methanol.

 Chemical Properties & Reactions of Alcohol:

In alcohols, (– OH) group is the functional group. Since the (– OH) group determines the chemical
properties of alcohols, the alcohols strikingly resembles in their chemical properties. However, 1 0, 20 & 30
alcohols differ in their chemical reactivity. This is due to the presence of different alkyl groups attached to
the carbinol carbon atom.
a) Reactions involving the H-atom of (– OH) group
b) Reactions involving the Hydroxyl (– OH) group
c) Reactions involving both alkyl & hydroxyl group
Reactions involving the H-atom of (– OH) group:

i) Reaction with highly electropositive metals: The hydrogen atom of the hydroxyl group is replaced by
alkali metals such as K, Na, etc, as well as alkaline earth metals such as Mg, Ca, etc.
Consequently, alkoxides are formed with the evolution of hydrogen gas. The metallic alkoxides remain
dissolved in alcohol.
2ROH + 2M 2ROM + H2 ↑ [M = Na, K]
2ROH + M (RO)2M + H2 ↑ [M = Mg, Ca]
Examples: 2CH3CH2OH + 2Na 2CH3CH2ONa + H2↑
Ethanol Sodium ethoxide
ii) Reaction with Grignard reagent: Alcohols react with Grignard reagent to form alkanes.
In these reactions, the alkyl group (R –) of the Grignard reagent combines with the hydrogen atom
of the (– OH) group in the alcohol producing the corresponding alkane.
ROH + R’MgX R’H + Mg(OR)X
Alcohol Grignard reagent Alkane
Examples: CH3CH2OH + CH3MgI CH4 + Mg(OC2H5)I
Ethanol Methylmagnesium Methane
iodide
iii) Acetylation of alcohol: When an alcohol (1 0 or 20) is heated with acetyl chloride or acetic anhydride
(in presence of pyridine), replacement of hydrogen atom of the (– OH) group with the acetyl group
(CH3CO –) occurs & acetyl derivative of the alcohol, i.e., acetate ester is produced.
Weak base, pyridine is used to remove HCl or CH3COOH produced in the reaction.
This reaction of replacing H atoms of alcoholic (– OH) group with acetyl group (CH3CO –) is called
acetylation.
O O
CH3 – C – Cl + H – OR CH3 – C – OR + HCl
Acetyl chloride Alcohol Acetate ester
O O
CH3 – C – O – C – CH3 + H – OR CH3 – C – OR + CH3COOH
Acetic anhydride Alcohol Acetate ester Acetic acid
Examples: CH3CO Cl + H OC2H5 CH3COOC2H5 + HCl
Acetyl chloride Ethanol Ethyl acetate
CH3CO OCOCH3 + H OC2H5 CH3COOC2H5 + CH3COOH
Acetic anhydride Ethanol Ethyl acetate
iii) Esterification: Alcohols react with carboxylic acids in presence of conc. H2SO4 or dry hydrogen
chloride gas to form ester & water. This reaction is called esterification. The reaction is reversible &
in this reaction (– OH) group of carboxylic acid gets combines with H atom of alcoholic (– OH)
group to form water molecule. Besides acting as a catalyst, conc. H 2SO4 also absorbs water produced
in the reaction to facilitate the forward process.
O O
R – C – OH + H – OR’ Conc. H2SO4/Δ R – C – OR’ + H2O
Carboxylic acid Alcohol Ester Water
Examples: CH3CO OH + H OC2H5 Conc. H2SO4/Δ CH3COOC2H5 + H2O
Acetic acid Ethyl alcohol Ethyl acetate

Reactions involving (– OH) group:

In these type of reactions, the (– OH) group of an alcohol is replaced by another atom or group.
i) Reaction with phosphorous halides: In the reaction with phosphorous halide, alkyl halide is produced
by the replacement of (– OH) group with the halogen atom.
(I) At ordinary temperature, alcohol reacts with phosphorous pentachloride with the formation of alkyl
chloride (RCl), phosphorous oxychloride (POCl3) & hydrogen chloride.
ROH + PCl5 RCl + POCl3 + HCl
Alcohol Alkyl halide
Examples: C2H5OH + PCl5 C2H5Cl + POCl3 + HCl
Ethanol Ethyl chloride
(II) PCl3 reacts with alcohol to produce alkyl chloride & phosphorous acid (H3PO3).
3ROH + PCl3 3RCl + H3PO3
Alcohol Alkyl chloride
Examples: 3C2H5OH + PCl3 3C2H5Cl + H3PO3
(III) Alcohol react with PBr3 & PI3 to form alkyl bromide & alkyl iodide respectively. PBr 3 & PI3 are
generally prepared in situ by the reaction between red phosphorous & bromine or iodine respectively.
4P + 6X2 = 4PX3
3ROH + PX3 3RX + H3PO3 [X = Br or I]
Examples: 3C2H5OH + PBr3 Red P/Br2 3C2H5Br + H3PO3
Ethanol Ethyl bromide
3C2H5OH + PI3 Red P/Br2 3C2H5I + H3PO3
Ethanol Ethyl bromide
ii) Reaction with halogen hydracids: Alcohols react with halogen hydracids to form haloalkanes.
The (– OH) group of an alcohol is replaced by halogen atom.
In these reactions, the order of reactivity of HX is: HI > HBr > HCl & the order of reactivity of
different classes of alcohols is: 30 alcohol > 20 alcohol > 10 alcohol.
R – OH + HCl Anhyd. ZnCl2 RCl + H2O
Alcohol (gas) Alkyl chloride
R – OH + HBr Δ/Trace of red P RBr + H2O
Alcohol (gas) Alkyl bromide
Examples: CH3OH + HCl Anhyd. ZnCl2 CH3Cl + H2O
iii) Reaction with thionyl chloride: Alcohols react with thionyl chloride (SOCl2) in presence of pyridine
to form alkyl halides. Due to liberation of SO2 & HCl vapours from the reaction mixture, the alkyl
halides produced are found to be more or less pure.
ROH + SOCl2 RCl + SO2 ↑ + HCl ↑
Alcohol Alkyl halide
Examples: C2H5OH + SOCl2 C2H5Cl + SO2 ↑ + HCl ↑
Ethanol Ethyl chloride
iv) Reaction with ammonia (ammonolysis): When the vapour of alcohol & excess ammonia are passed
over heated catalyst alumina (Al2O3), or copper chromite (CuCr 2O4) at 3000C, primary amine is first
formed. The reaction is not stopped at this stage. Ultimately a mixture of primary, secondary, tertiary
amines & tetra-alkyl ammonium salt is obtained.
CuCr2O4 or Al2O3
CH3OH + NH3 High pressure, 3000C CH3NH2 + H2O
Methanol Methyl amine
( 10 )
CuCr2O4 or Al2O3
CH3NH2 + CH3OH High pressure, 3000C
(CH3)2NH + H2O
Dimethyl amine
( 20 )
CuCr2O4 or Al2O3
(CH3)2NH + CH3OH High pressure, 3000C
(CH3)3N + H2O
Trimethyl amine
( 30 )

v) Reaction with red phosphorous & hydroiodic acid: Alcohols are reduced to alkanes by concentrated
aqueous solution of hydroiodic acid in presence of small quantity of red phosphorous at high
temperature (1500C), The reaction is carried out in a closed container.
ROH + HI Red P (1500C) [Closed vessel] [R – I] HI/[– I2] R – H
Alcohol Alkane
Examples: C2H5OH + HI Red P (1500C) [Closed vessel] [C2H5I] HI/[– I2] C2H6
Ethanol Ethyl iodide Ethane
Reactions involving both alkyl & (– OH) group:

i) Dehydration of alcohols: An alcohol, on being heated with a suitable dehydrating agent, undergoes
intramolecular dehydration to yield an alkene. Conc. H2SO4 & phosphoric acid or alumina may be used
as dehydrating agents. Depending on the nature of alcohol, sulphuric acid of different concentrations is
used & the reaction is made to occur at different temperatures.
The ease of dehydration of alcohols follows the order: 30 alcohol > 20 alcohol > 10 alcohol.
Conc. H2SO4 , Heat
–C–C– C = C + H2O
Or Alumina, Heat
H OH Alkene
Alcohol
Conc. H2SO4 (excess), 1700C
Examples: CH3CH2OH CH2 = CH2 + H2O
Or Al2O3 , 3500C
Ethanol (10) Ethylene
ii) Oxidation of alcohols: Depending on their types, alcohols undergo oxidation to give different products.
Oxidising agents generally used are chromium trioxide (CrO3) & pyridine, acidified potassium or
sodium dichromate (K2Cr2O7/H2SO4 , Na2Cr2O7 / H2SO4), acidic or alkaline potassium permanganate
(KMnO4) etc.
(I) A primary alcohol on oxidation first gives an aldehyde which on further oxidation produces an acid
with the same number of carbon atoms as the alcohol.
H OH
[O] / [– 2H] [O]
R – CH2OH R–C=O R–C=O
10 Alcohol Aldehyde Carboxylic acid
In this reaction, (– CH2OH) group is converted into (– COOH) group through the formation of
intermediate (– CHO) group.
Na2Cr2O7 / H2SO4 Na2Cr2O7 / H2SO4
Examples: CH3CH2OH CH3CHO CH3COOH
[O] [O]
Ethyl alcohol Acetaldehyde Acetic acid
NOTE: Pyridinium chlorochromate (PCC) is a suitable reagent for controlled oxidation of primary
alcohol to aldehyde.
CrO3 . Pyridine . HCl
CH3(CH2)5CH2OH CH3(CH2)5CHO
Or C5H5NH⨁CrO3ClΘ
1-Heptanol (PCC) CH2Cl2 (solvent) heptanal (78%)
(II) A secondary alcohol on oxidation, first gives a ketone with the same number of carbon atoms.
Ketones are quite resistant to further oxidation. But on prolonged treatment with strong oxidising
agent, ketones are oxidised to carboxylic acids with lesser number of carbon atoms.
Symmetrical ketones on oxidation give rise to two carboxylic acids. But in case of unsymmetrical
ketones, C – C bond fission occurs in such a manner that the smaller alkyl group remains attached
to the carbonyl group (Popoff’s rule) & the two carboxylic acids produced by such type of fission
are the major products.
O
[O] [O]
RCH2CHOHCH2R RCH2 – C – CH2R RCH2COOH + RCOOH
Alcohol ( 20) Symmetrical ketone
O
[O] [O]
Examples: CH3CH2CHOHCH2CH3 CH3CH2 – C – CH2CH3 CH3CH2COOH + CH3COOH
3-Pentanol 3-Pentanone Propanoic acid Acetic acid

O
[O] [O]
RCH2CH2CHOHR RCH2CH2 – C – R RCH2COOH + RCOOH
Alcohol ( 20) Unsymmetrical ketone
O
[O] [O]
Examples: CH3CH2CH2CHOH CH3 CH3CH2CH2 – C – CH3 CH3CH2COOH + CH3COOH
2-Pentanol 2-Pentanone Propanoic acid Acetic acid
Major products
(III) A Tertiary alcohols are generally resistant to oxidation under normal condition. They cannot be
oxidised even by using a strong oxidising agent in neutral or alkaline medium. However, they are
oxidised by very strong oxidising agent in acidic medium. In such oxidation, tertiary alcohol first gets
dehydrated to yield an alkene, which on oxidation, produces a ketone with lesser number of carbon
atoms than the parent alcohol. The ketone thus produced, is subsequently oxidised to carboxylic acid.
CH3 CH3
Na2Cr2O7 / H2SO4 Na2Cr2O7 / H2SO4
CH3 C CH3 CH3 C CH2
[– H2O]
OH 2-methylpropene
tert-Butyl alcohol
CH3
Na2Cr2O7 / H2SO4
CH3COOH + CO2 + H2O CH3 – C = O + CO2 + H2O
Acetic acid Acetone
iii) Dehydrogenation in presence of catalyst: When vapours of alcohols are passed over heated copper
at 3000C, different classes of alcohols yield different products. Since, it is a dehydrogenation reaction
(no oxidising agent is used), so the product obtained, aldehyde or ketone, is not further oxidised to
carboxylic acid.
Through this process of oxidation is less expensive, a number of alcohols become unstable at this
high temperature.
H H H
R – CH – O Cu, 3000C [Alcohol vapour] R – C = O + H2
( 10) Alcohol Aldehyde
H H O
R – C – O Cu, 3000C [Alcohol vapour] R – C – R + H2
R
( 20) Alcohol Ketone
O
Examples: CH3CH2OH Cu, 300 C [Alcohol vapour]
0
CH3 – C – H + H2
Ethanol Acetaldehyde
O
CH3CHOHCH3 Cu, 300 C [Alcohol vapour]
0
CH3 – C – CH3 + H2
Propan-2-ol Acetone
iv) Haloform reaction: Ethyl alcohol & secondary alcohols containing CH3CH(OH) group react with
halogens (Cl2 , Br2 or I2) in alkaline solution (NaOH or KOH) to produce chloroform (CHCl 3) ,
bromoform (CHBr2) or iodoform (CHI3) respectively. This reaction is called haloform reaction.

Illustration: 1. Among the isomeric alcohols having molecular formula C4H9OH, which is the strongest
acid & which is the weakest acid?
Solution: Among alcohols the order of acidic strength is 10 > 20 > 30.
Among the isomeric alcohols having molecular formula C 4H9OH tert-butyl alcohol is the
weakest acid & n-butyl alcohol is the strongest acid.
CH3
CH3CH2CH2CH2 – OH CH3 – C – OH
CH3
Butan-1-ol (10) 2-Methylpropan-2-ol (30)
(n-Butyl alcohol) (tert-Butyl alcohol)
Strongest acid Weakest acid
Illustration: 2. Name the reagent used in the following reactions:
(i) Oxidation of a primary alcohol to carboxylic acid
(ii) Oxidation of a primary alcohol to an aldehyde
(iii) Dehydration of propan-2-ol to propene
(iv) Butan-2-one to butan-2-ol
Solution: (i) Acidified solution of KMnO4 (or acidified K2Cr2O7).
(ii) Hot reduced copper (or pyridinium chlorochromate, PCC), using CH2Cl2 as solvent.
(iii) Hot conc. H2SO4.
(iv) Lithium aluminium hydride, LiAlH4, using dry there as solvent.
Illustration: 3. Arrange the following compounds in the increasing order of the property indicated against
each. Give reasons for your answer.
(i) CH3CH2OH, CF3CH2OH, CCl3CH2OH – Acid strength.
(ii) 2-Methyl-2-propanol, 1-Butanol & 2-Butanol – Reactivity towards sodium.
Solution: (i) The presence of electron withdrawing groups in the alkyl group stabilizes the alkoxide ion
& hence promotes the dissociation of alcohol making it a stronger acid. Since, F is stronger
electron withdrawing group than Cl, therefore, CF 3CH2OH is stronger acid than CCl3CH2OH.
CH3CH2OH is the weakest acid due to electron releasing effect of alkyl group which
destabilizes the alkoxide ion by concentration of negative charge. Hence, the acidic strength
increases in the order: CH3CH2OH < CCl3CH2OH < CF3CH2OH.
Illustration: 4. Give structures of the products you would expect when each of the following alcohols
reacts with: (a) HCl – ZnCl2 (b) HBr & (c) SOCl2
(i) Butan-1-ol (ii) 2-Methylbutan-2-ol
Solution: (i) CH3CH2CH2CH2OH + HCl ZnCl2 CH3CH2CH2CH2Cl + H2O
CH3CH2CH2CH2OH + HBr CH3CH2CH2CH2Br + H2O
CH3CH2CH2CH2OH + SOCl2 CH3CH2CH2CH2Cl + SO2 + HCl
CH3 CH3
(ii) CH3 – C – CH2 – CH3 + HCl CH3 – C – CH2 – CH3
OH Cl
CH3 CH3
CH3 – C – CH2 – CH3 + HBr CH3 – C – CH2 – CH3
OH Br
CH3 CH3
(ii) CH3 – C – CH2 – CH3 + SOCl2 CH3 – C – CH2 – CH3
OH Cl
Illustration: 5. Predict the major product of acid catalysed dehydration of Butan-1-ol.
Solution: CH3CH2CH2CH2OH H+ CH3CH2CH = CH2 + CH3CH = CHCH3
A mixture of but-1-ene & but-2-ene is formed. But-2-ene is formed due to rearrangement of
intermediate carbocation to give secondary carbocation, & is the major product.

 Distinction between 10 , 20 and 30 alcohols

 Dichromate test (Oxidation test):
Primary Secondary Tertiary
R − CH2 OH R R
Na2Cr2O7 R’ – C – OH R’ – C – OH
[O]
+ H2SO4 H R’’
O [O] Na2Cr2O7 [O] Na2Cr2O7

+ H2SO4 + H2SO4
R–C–H
Aldehyde R No reaction
(solution remain orange)
[O] Na2Cr2O7 R’ – C = O
+ H2SO4 Ketone
(orange solution
O becomes green)
R – C – OH
Acid
(orange solution
becomes green)
 Lucas test :- Lucas reagent is a solution of conc. HCl with anhydrous ZnCl2 with Lucas reagent,
Primary alcohols – No cloudiness
Secondary alcohols – Cloudiness in 5 minutes
Tertiary alcohols – Cloudiness immediately
Victor Meyer’s test
Primary Secondary Tertiary
R
RCH2OH R R C OH
CHOH R
P / I2 or HI R P / I2 or HI
P / I2 or HI
R
RCH2I R C I
R R
AgNO2 CHI
R AgNO2
RCH2NO2 AgNO2
R
HONO R R C NO2
CHNO2 R
R – C – NO2 R
HONO HONO
NOH
Nitrolic acid R
C – NO2 no reaction
NaOH R
NO NaOH
Pseudo nitrol
Blood red colour colourless
NaOH
Blue colour

Interconversions Among Different Classes Of Alcohols
I. Primary (10) alcohol to secondary (20) alcohol containing the same number of carbon atoms:
0 HBr
CH3CH2CH2OH Conc. H2SO4 / 1700 C CCH3 – CH = CH2 CH3CHBrCH3
Or, Al2O3 / 350 C Markownikoff addition
1-Propanol Propene 2-Bromopropane
Conc. H2SO4 Aq. KOH Heat
H2O/Heat
CH3CHCHCH3 CH3CHOHCH3
OSO3H 2-Propanol
Isopropyl hydrogen sulphate (20 alcohol)
II. Secondary (20) alcohol to primary (10) alcohol containing the same number of carbon atoms:
Conc. H2SO4 / 1700C HBr/organic peroxide
CH3CHOHCH3 CH3 – CH = CH2 CH3CH2CH2Br
2-Propanol Or, Al2O3 / 3500C Propene
Anti-markownikoff
1-Bromopropane
addition
B2H6 Aq. KOH
H2O2 / NaOH
(CH3CH2CH2 – )3B CH3CH2CH2OH
Tripropylborane 1-Propanol (10 alcohol)
CH3CH2CH(OH)CH3 HI CH3CH2CHICH3 (CH3)3N CH3CH2CHCH3 AgOH/Δ CH3CH2CH=CH2

2-Butanol (CH3)3N⨁IΘ 1-Butene
Moist HBr/organic peroxide
CH3CH2CH2CH2OH CH3CH2CH2CH2Br
AgOH Anti-markownikoff
2-Butanol 1-Bromobutane addition
(10 alcohol)
III. Primary (10) alcohol to tertiary (30) alcohol containing the same number of carbon atoms:
Conc. H2SO4 / 1700C HI Moist AgOH
(CH3)2CHCH2OH (CH3)2C = CH2 (CH3)3CI
Or, Al2O3 / 3500C Markownikoff addition
2-Methyl-1-propanol 2-methylpropene 2-iodo-2-methylpropane
(CH3)3COH
2-Methyl-2-propanol
(30 alcohol)
IV. Tertiary (30) alcohol to primary (10) alcohol containing the same number of carbon atoms:
CH3
Conc. H2SO4 / 1700C B6H5 H2O2
(CH3)3COH (CH3)2C = CH2 Ether (CH3CHCH2 –)3B (CH3)2CHCH2OH
NaOH
2-Methyl-2-propanol 2-methylpropene Triisobutylborane 2-Methyl-1-propanol
(30 alcohol) (10 alcohol)
V. Secondary (20) alcohol to tertiary (30) alcohol:

CH3
K2Cr2O7 / H2SO4 CH3MgI H2O
CH3CHOHCH3 [O]
CH3COCH3 Ether
CH3 – C – OMgI (CH3)3COH
2-Propanol Propanone CH3 2-methyl-2-propanol
(20 alcohol) (30 alcohol)
VI. Higher alcohol to lower alcohol (step down):

CH3
Conc. H2SO4 / 1700C O3 Zn/H2O LiAlH4
CH3CH2OH CH2 = CH2 H2C CH2 2HCHO CH3OH
[H]
Ethanol Ethylene O O Formaldehyde Methanol
(2 carbon) Ethylene ozonide (1 carbon)

Part – B : PHENOLS
1 INTRODUCTION
An phenol, C6H5OH or Hydroxy benzene was discovered by Runge in the middle oil fraction of
coaltar distillation who named is ‘carbolic acid’ (carbo = coal, oleum = oil).
Phenol containing 5% water is liquid at room temperature & is termed as carbolic acid. It is also
present (in traces) in human urine.
 General formula : Phenols are the compounds in which hydroxyl ( − OH) group is directly linked to
aromatic ring having formula C6H5OH

2 CLASSIFICATION & NOMENCLATURE OF PHENOLS
They can be mono, di or trihydric phenols depending upon whether they contain one, two or three
hydroxyl groups on the benzene ring. Methyl phenols are called cresols or they are hydroxyl derivatives
of toluene.
Monohydric phenols: Examples are phenol & cresols.
OH OH OH OH OH
CH3 H3C CH3
CH3
CH3
Phenol 2-Methylphenol 3-Methylphenol 4-Methylphenol 2, 6-Dimethylphenol
Hydroxy benzene (o-cresol) (m-cresol) (p-cresol)
(Benzenol)
Dihydric phenols: Examples are dihydroxy benzenes (1, 2 & 1, 3 & 1, 4).
OH OH OH
OH
OH
OH
1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,4-Dihydroxybenzene
(Benzene-1,2-diol) (Benzene-1,3-diol) (Benzene-1,4-diol)
Or Catechol Or Resorcinol Or Quinol
Trihydric phenols: Examples are trihydroxy benzenes (1, 2, 3 & 1, 2, 4 & 1, 3, 5).
OH OH OH
OH OH
OH HO OH
OH
1,2,3-Trihydroxybenzene 1,2,4-Trihydroxybenzene 1,3,5-Trihydroxybenzene
(Benzene-1,2,3-triol) (Benzene-1,2,4-triol) (Benzene-1,3,5-triol)
Or Pyrogallol Or Hydroxyquinol Or Phloroglucinol

Further they can be substituted phenols. Examples are:

OH OH OH
NO2
NH2
Cl
2-Nitrophenol 3-Aminophenol 4-Chlorophenol
(o-Nitrophenol) (m-Nitrophenol) (p-Nitrophenol)
OH OH CH2OH
Br O2N NO2
Br NO2 OH
2,4-Dibromophenol 2,4,6-Trinitrophenol 4-(Hydroxy methyl)
(Picric acid) phenol
Also phenols containing aldehydic, ketonic carboxyl or an acid ester groups are
named as hydroxyl derivatives of the parent aromatic compound . Examples are:
OH OH CH2OH
2 2 2
1 CHO 1 COCH3 1 COOH
2-Hydroxybenzaldehyde 2-Hydroxyacetophenone 2-Hydroxybenzoic acid

(o-Hydroxybenzaldehyde) (o-Hydroxyacetophenone) (o-Hydroxybenzoic acid)
Or Salicylaldehyde Or Salicylic acid
OH OH OH
4 4 3
1
1
COOCH3
1
COCH3 SO3H
4-Hydroxyacetophenone 4-Hydroxyacetophenone Methyl-3-hydroxy benzoate
(p-Hydroxyacetophenone) (p-Hydroxybenzene (Methyl-m-hydroxy
sulphonic acid) benzoate)
Phenols are distinctly acidic while alcohols are neutral. Phenols have a
characteristic odour & are toxic in nature. They posses strong intermolecular
hydrogen bonding & hence, the boiling points of phenols are higher than aliphatic
alcohols. The first member of the series is the most important compound & is
named phenol.

3 METHODS OF PREPARATION OF PHENOLS

SO3H SO3Na ONa OH
From Aryl Sulphonic

+ NaOH –H2O +2NaOH – NaCl
Acids –Na2SO3, –H2O +HCl
Benzene Sod. Benzene Sod. Phenoxide Phenol

Sulphonic acid sulphonate
Cl ONa OH
From Aryl Halides

+ NaOH 623K H+ + Na+
(Dow’s Process) 300 atm, – HCl
Chlorobenzene Sod. Phenoxide Phenol
N2+ Cl− OH
From Diazonium
+ H2O Δ + N2 + HCl
Salts
Benzene Phenol
diazonium
chloride
Decarboxylation of OH ONa OH
Sodium Salt of
COONa
Salicylic acid
+ NaOH CaO +HCl + NaCl
Δ
Sodium salicylate Sod. Phenoxide Phenol
MgBr OMgBr OH
From Aryl Halides

+ ½ O2 ether H2O/H+ 0 + Mg(OH)Br
(Dow’s Process)
Phenyl Phenoxy Phenol

magnesium magnesium
bromide bromide
4 COMMERTIAL METHOD OF PREPARATON OF PHENOLS

a) From Cumene (Isopropyl benzene): The starting material for the preparation of phenol is cumene.
Cumene itself is prepared by Friedel-Craft alkylation of benzene with propene. Cumene is oxidised by
air to cumene hydroperoxide, which on treatment with dilute sulphuric acid gives phenol.
b) From Benzene (Rasching Process): The method involves heating of benzene, HCl & air over a
catalyst (mixture of CuCl2 & FeCl3) at 500K when chlorobenzene is produced. It is then heated with
super steam at 750 K to give phenol
USES OF PHENOL
 In the manufacture of drugs like salicylic acid, phenacetic, aspirine, salol, etc.
 For the manufacture of Bakelite by polymerising with formaldehyde.
 For the manufacture of cyclohexanol used as solvent for rubbere.
 For the manufacture of phenolphthalein, picric acid.
 As a preservative for ink.

Illustration: 1. Complete the following reaction :
Conc H2SO4 /Δ (A) NaOH /Δ (B) H2SO4 (C)
Benzene
Solution: SO3H ONa OH
Conc H2SO4 /Δ NaOH /Δ H2SO4
Benzene Benzene sulphonic Sodium phenoxide Phenol

acid
Illustration: 2. What happen when chlorobenzene is fused with NaOH at 623K & 320 atm pressure after
reaction with HCl?
Solution: Chlorobenzene is fused with NaOH at 623K & 320 atm pressure to produce sodium phenoxide,
which gives phenol on acidification.
Cl ONa OH
623K/320 atm HCl
+ 2NaOH
Chlorobenzene Sodium phenoxide Phenol

Illustration: 3. Write the chemical equation for the preparation of phenol from benzene using oleum &
sodium hydroxide.
Solution: The chemical equation for the preparation of phenol from benzene by using oleum & sodium
hydroxide is given below:
SO3H OH
Heat fuse
+ H2SO4 + SO3 + NaOH + Na 2SO3
Oleum
Benzene Benzene sulphonic Phenol
acid
Illustration: 4. How is phenol obtained from aniline?
Solution: NH2 𝑁2+ 𝐶𝑙 − OH
NaNO2 / HCl (273 – 278 K) H2O / warm

Diazotisation + N2 + HCl
Aniline Benzene diazonium Phenol

chloride
Illustration: 5. How phenol is prepared with the help of sodium salicylate?
Solution: OH ONa OH
COONa
+ NaOH CaO +HCl + NaCl
Δ
Sodium salicylate Sod. Phenoxide Phenol

5 PROPERTIES OF PHENOLS
 Physical Properties of Phenols:
a) Colour: Pure phenols are either colourless liquids or deliquescent solids. However, they usually turn to
pink colour on exposure to air & light. The colour is probably due to its oxidation in air.
b) Odour: Phenols have a peculiar characteristic smell & a strong corrosive action on skin.
c) Boiling point: The boiling points of phenols are much higher than the corresponding aromatic
hydrocarbons & the haloarenes.
Compound B.P. (K) Compound B.P. (K)
C6H6 353 C6H5Br 439
Benzene Bromobenzene
C7H8(C6H5 – CH3) 383 C6H5Cl 405
(Molecular mass = 92) Chlorobenzene
C6H5OH 454 C6H5 – C2H5 413
Phenol Ethylbenzene
(Molecular mass = 94)
The higher boiling point of phenols is due to presence of intermolecular hydrogen bonding in them.
------- O H ------ O H ------- O H -------
Thus, phenols (like alcohols) exist as associated molecules

d) Solubility: Phenols are soluble in water due to H-bonding, but solubility of phenols in water is much
lower than that of alcohols because of benzene ring (larger hydrocarbon part) present in their molecules.
Further, phenols are readily soluble in organic solvents such as alcohol, benzene, ether, etc.
e) Nature: Phenols are poisonous in nature but acts as antiseptic & disinfectant.
 Chemical Properties & Reactions of Phenols:
a) Acidity of phenols:
i. Phenols are weak acids. They turn blue litmus red. They are weaker acid than H2CO3.
ii. Phenols are stronger acids than alcohols (due to resonance) but weaker acids than carboxylic acids.
iii. Electron withdrawing groups increase acidity of phenol.
iv. Electron donating groups decrease acidity of phenol.
v. Phenols form the intermolecular hydrogen binding & their melting point & boiling point are much
higher than hydrocarbons of the compound of the comparable molecular weights.
b) Alkylation of phenols:
OH OCH3
+ CH3I Δ + NaI
Phenol Anisole
(ether)
OH OC2H5
+ CH3I C2H5I + NaI
Phenol Phenetole
(ether)

c) Distillation with Zn:

OH
+ Zn dust + ZnO
Phenol Benzene
d) Benzoylation (Schotten Beumann reaction):
OH COOC6H5
+ C6H5COCl NaOH + NaCl + H2O

(Benzoyl chloride)
Phenol Phenyl benzoate

e) Reimer – Tiemann reaction:
ONa ONa ONa
OH
CHCl2 CH
+ CHCl3 NaOH, 340K 2NaOH OH
– NaCl, – 2H2O – NaCl
– H2O
OH ONa
CHO CHO
Dil. HCl
– HCl
f) Kolbe’s reaction:
OH ONa OCOONa OH
COOH
+ NaOH + CO2 , 400K HCl
4 – 7 atm
Phenol Sod. phenoxide Sod. salicylate Salicylic acid
(CH3CO)2O [+ Conc. H2SO4] C6H5OH + POCl3 CH3OH (Reflux)
OCOCH3 OH OH
COOH COOC6H5 COOCH3
CH3COOH +
2-Acetoxy benzoic acid Phenyl salicylate Methyl salicylate

(Aspirine) (Salol) (Oil of winter green)
Aspirine is used as analgesic Oil of winter green is used in

& antipyretic. Salol is used as antiseptic perfumery, as flavouring agent
in food & drinks.

g) Reimer – Tiemann reaction:

ONa ONa ONa
OH
CHCl2 CH
+ CHCl3 NaOH, 340K 2NaOH OH
– NaCl, – 2H2O – NaCl
– H2O
OH ONa
CHO CHO
Dil. HCl
– HCl
NOTE: If CCl4 is used instead of CHCl3 salicylic acid is formed.

OH ONa ONa
CCl3 C(OH)3
+ CCl4 NaOH, 340K 3NaOH
– NaCl, – 2H2O – 3NaCl
Phenol
– H2O
OH ONa
COOH COOH
Dil. HCl
– NaCl
Salicylic acid
h) OH
O2 / CrO3 O O
Phenol Benzoquinone
(pink colour)
C2H5N2Cl
(Coupling reaction)
C6H5 – N = N – C6H5OH
p-Hydroxyazobenzene
(orange – red dye)
i) OH OH OH
OH
K2 S 2 O 8 +
Alkaline solution
OH
Phenol Quinol Catechol
(Major) (Minor)

j) Phenolphthalein reaction:
OH OH O
CO C
+ O Conc. H2SO4 O
CO C
Phenol Phthalic anhydride
OH OH
Phenolphthalein
k) Libermann’s nitroso reaction:
OH OH O
NaNO2
Conc. H2SO4
NO NOH
OH O
H2O O N OH
Conc. H2SO4
Indophenol (red)
H NOH
H2O NaOH
O N ONa
Sodium salt of Indophenol

𝑙) Electrophilic substitution reactions of phenol:
Phenolic (– OH) is o, p – directing group.
(i) Bromination:
OH OH OH OH
Br Br Br
Br3 (aq.) + Br2 CS2 +
2,4,6-Tribromophenol Phenol Br
(White ppt.) Quinol Catechol
(ii) Sulphonation:
OH OH OH
SO3H
H2SO4 H2SO4
373 K 293 K
SO3H Phenol

(iii) Nitration:
OH OH OH OH
O2N NO2 NO2

Conc. HNO3 Dil. HNO3 +
H2SO4 H2SO4
2,4,6-Trinitrophenol Phenol NO2

(Picric acid)
OCH3 OCH3
Br
+ Br2 in acetic acid
(Bromination)
Br
p-Bromo anisole (Minor)
(Major)
OCH3 OCH3 O – CH3
CH3
+ CHCl3/Anhydr. AlCl3
(Friedel craft alkylation)
CH3 (Anisole)
p-Methoxy toluene (Minor)
(Major)
OCH3 OCH3
NO2
+ HNO3 (Conc.)/H2SO4 (Conc.)
(Nitration)
NO2
p-Nitro anisole (Minor)
(Major)
Illustration: 1. Write the structures of the major products expected from the following reactions:
(i) Mononitration of 3-methylphenol
(ii) Dinitration of 3-methylphenol
(iii) Mononitration of phenyl ethanoate.
Solution: (i) OH OH
O2N
CH3 CH3
NO2
OH OCOCH3
(ii) O2N (iii)
CH3
NO2 NO2

Illustration: 2. Complete the following equation supplying A & B:

OH
Zn dust (A) H2SO4 / SO3 (B)
Solution: OH SO3H
Zn dust H2SO4 / SO3
Illustration: 3. Write a short note on Kolbe’s reaction & Reimer-Tiemann reaction.

Solution: Kolbe’s reaction: when sodium phenoxide is heated with CO2 at 400K & at a pressure of 4-7 atm.
Sodium salicylate is formed as the major product. This on acidification yields salicylic acid.
OH ONa OH OH
COONa COOH
NaOH 400K/ 4-7atm (CO2) H+
Reimer-Tiemann reaction: Treatment of phenol with chloroform in the presence of aqueous

alkali at 340K results in the formation of o-hydroxybenzaldehyde (salicylaldehyde) &
p-hydroxybenzaldehyde, the ortho isomer being the major product.
OH ONa ONa OH
CHCl2 CHO CHO
CHCl3, aq. NaOH NaOH H3O+
Illustration: 4. Complete the following reactions:

(i) OH
+ NaOH (A) + H2O
(ii) OH
Pyridine
+ CH3COCl (A) + HCl
Solution: (i) OH ONa
+ NaOH + H2O
Phenol Sod. phenoxide

(ii) OH OCOCH3
Pyridine
+ CH3COCl + HCl
Phenol Phenyl acetate

Illustration: 5. Arrange the following compounds in increasing order of their acid strength:
Propan-1-ol; 2,4,6-trinitrophenol; 3-nitrophenol; 3,5-dinitrophenol; phenol; 4-methylphenol
Solution: Propan-1-ol; 4-methylphenol; phenol; 3-nitrophenol; 3,5-dinitrophenol; 2,4,6-trinitrophenol.

.
Part – C : ETHERS
1 INTRODUCTION
Ethers are a class of compounds which contain an oxygen atom bonded to two alkyl groups (same
or different). When both the alkyl groups are same they are designated as simple or symmetrical
ethers & when both are different, they are called mixed or unsymmetrical ethers.
RO – H + HO – R R – O – R + H2O
Ether molecule may also be formed by the replacement of one H atom from an alkane (RH)
molecule with an alkoxy group (– OR). So it is also called alkoxyalkane, & it is named
accordingly in the IUPAC system.
 General formula : R – O – R [where, R is alkyl or aryl group].
Ethers form a homologous series with the general formula CnH2n + 2O (same as monohydric alcohols),
where the value of ‘n’ is always more than 1. the functional group of ethers is (C – O – C).

2 CLASSIFICATION OF ETHERS

 Simple or Symmetrical Ethers:
The ethers in which the two alkyl groups are same are called simple or symmetrical ethers (ROR).
Examples: CH3 – O – CH3 ; C2H5 – O – C2H5 ; C6H5 – O – C6H5 ; C6H5CH2 – O – CH2C6H5
Dimethyl ether Diethyl ether Diphenyl ether Dibenzyl ether
 Mixed or Unsymmetrical Ethers:
The ethers in which the two different alkyl groups bonded to the oxygen atom are called mixed or
unsymmetrical ethers (ROR’).
Examples: CH3 – O – C2H5 ; C2H5 – O – C3H7 ; C6H5 – O – CH3 ; C6H5CH2 – O – C6H5
Ethyl methyl ether Ethyl propyl ether Methyl phenyl ether Benzyl phenyl ether
 Ethers e further classified into the following two categories:
(a) Aliphatic ethers: In which R & R’ (same or different) are both alkyl groups.
Examples: CH3 – O – CH3 ; C2H5 – O – C2H5 ; C6H5 – O – C6H5 ; C6H5CH2 – O – CH2C6H5
Dimethyl ether Diethyl ether Diphenyl ether Dibenzyl ether
(b) Aromatic ethers: In which either one or both R & R’ groups are aryl groups.
Examples: C6H5 – O – C2H5 ; C6H5 – O – C7H15 ; C6H5 – O – CH3 ; C6H5 – O – C6H5
Ethyl phenyl ether Heptyl phenyl ether Methyl phenyl ether Diphenyl ether
Aromatic ethers are further subdivided into:
(i) Phenolic ethers: in which one of the groups is alkyl while the other is aryl. They are also
called as aryl alkyl ethers or phenolic ethers.
Examples: C6H5 – O – C2H5 ; C6H5 – O – CH3
Ethyl phenyl ether Methyl phenyl ether
(ii) Diaryl ethers: in which both are aryl groups.
Examples: C6H5 – O – C6H5 (Diphenyl ether)

3 NOMENCLATURE OF ETHERS

There are two systems for naming ethers.
(a) Common names: In this system, ethers are named after the alkyl groups attached to oxygen atom &
adding the word ether. When both alkyl groups are same, the prefix di- is used. In case of
unsymmetrical ethers two alkyl groups are named in alphabetical order.
Examples: CH3 – O – CH3 ; C2H5 – O – C2H5 ; C2H5 – O – CH3 ; C2H5 – O – C3H7
Dimethyl ether Diethyl ether Ethyl methyl ether Ethyl propyl ether
CH3CH2CH2 – O – CH(CH3)2 ; (CH3)2CH – O ; O – CH3

Isopropyl n-propyl ether
Isopropyl phenyl ether Methyl phenyl ether
(b) IUPAC names: In this system, according the IUPAC system of nomenclature, ether are regarded as
hydrocarbon derivatives in which a hydrogen atom is replaced by an – OR or – OAr group, where
R and Ar represents alkyl and aryl groups, respectively.
The larger R group is chosen as the parent hydrocarbon.

4 ISOMERISM IN ETHERS
The following three types of isomers:
a) Functional isomerism with monohydric alcohols: Ethers are isomeric with alcohols
(monohydric), since both have same general formula, CnH2n + 2O, but different functional groups.
Examples: Molecular formula Alcohol Ether
C2H6O CH3CH2OH CH3 – O – CH3
(Ethyl alcohol) (Dimethyl ether)
C3H8O C3H7OH CH3 – O – C2H5
(Propyl alcohol) (Ethyl methyl ether)
C4H10O C4H9OH C2H5 – O – C2H5
(Butyl alcohol) (Diethyl ether)
C7H8O C6H5CH2OH C6H5 – O – CH3
(Benzyl alcohol) (Methyl phenyl ether)
b) Metamerism: Ethers show isomerism among themselves due to different alkyl groups attached to
polyvalent oxygen atom.
Examples: The molecular formula C4H10O exhibits three isomers.
C2H5 – O – C2H5 ; CH3 – O – CH2CH2CH3 ; CH3 – O – CH – (CH3)2
(i) Diethyl ether (ii) Methyl n-propyl ether (iii) Methyl isopropyl ether
(i) & (ii) are metamers; similarly (i) & (iii) are metamers. Only those ethers which contain more than
three carbon atoms exhibit this type of isomerism.
Examples: C8H10O C6H5 – O – CH2CH3 ; C6H5CH2 – O – CH3 are metamers.
Ethyl phenyl ether Benzyl methyl ether
c) Chain isomerism: Ethers having different carbon chain skeletons are called chain isomers.
Examples: CH3CH2CH2CH2 – OCH3 ; CH3 – CH – CH2 – OCH3
1-Methoxybutane CH3
1-Methoxy-2-methylpropane
Illustration: 1. Give the structural formula of:

(i) Chloromethyl methyl ether; (ii) Di-isopropyl ether;
(iii) Bis (2-methoxyethyl) ether; (iv) 1,2-Dimethoxyethane
Solution: (i) ClCH2 – O – CH3; (ii) (CH3)2CHOCH(CH3)2;
(iii) (CH3OCH2CH2)2O; (iv) CH3OCH2 – CH2OCH3
Illustration: 2. Give the structural formula for all the isomeric ethers of the formula C 5H12O.
Solution: CH3CH2CH2OCH2CH3 ; CH3CH2CH2CH2OCH3 ;
CH3
CH3CHCH2OCH3 ; CH3 – C.O.CH3 ; CH3CH.OCH2CH3 ;
CH3 CH3 CH3
Illustration: 3. Give the IUPAC names to the following:
(i) C6H5OC2H5 ; (ii) CH3CH2OCHCH2CH3 ; (iii) CH3CH2OCHCH3
CH3 Cl
Cl CH3
(iv) OCH2CH2Br ; (v) OCH3 ; (vi) CH3OCH2CHCH3
Solution: (i) Ethoxybenzene; (ii) 2-Ethoxybutane; (iii) 1-Chloro-1-ethoxyethane;

(iv) (2-Bromoethoxy) benzene; (v) 1-Chloro-2-methoxybenzene;
(vi) 1-Methoxy-2-methylpropane
Illustration: 4. To which category of ethers do the following belong:
(a) Phenetole, (b) 2-Methoxy-2-phenylpropane, (c) Di tert-butyl ether.
Solution: (a) Aromatic ether, (b) Unsymmetrical ether, (c) Symmetrical ether.

5 METHODS OF PREPARATION OF ETHERS
Williamson’s Synthesis
CH3Br + Na+ O− C2H5 CH3OC2H5 + NaBr
Methyl bromide Sodium ethoxide Methoxy ethane
Dehydration of Alcohol
2C2H5OH Conc. H2SO4 / 413 K C2H5OC2H5 + H2O
Diethyl ether
Diazomethane on
CH3CH2OH + CH2N2 CH3CH2 – OCH3 + N2
Alcohol
Diazo methane Methoxy ethane
CH3 CH3
From Alkenes
CH3 – C = CH2 + C2H5OH H2SO4 CH3 – C – CH3
Isobutylene OC2H5
Ethyl tert-butyl ether
From Grignard Reagent
CH3OCH2Cl + CH3MgI CH3OCH2CH3 + Mg(I)Cl
Monochloro Ethyl methyl Chloro
dimethyl ether ether Magnesium
Iodide
Alkyl Halide with Dry
2(CH3CH2Br) + Ag2O 2(CH3CH2) – O + 2AgBr
Silver Oxide
Illustration: 1. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable
method. Give reason.
Solution: Secondary & tertiary alcohols undergo dehydration to form alkenes as the major products, hence
they cannot be used for preparing ethers.
CH3 – CH – CH3 H2SO4 / Δ CH3 – CH = CH2 + H2O
OH
CH3 CH3
CH3 – C – CH3 H2SO4 / Δ CH3 – C = CH2 + H2O
CH3
Illustration: 2. How can each of the following ethers be prepared by Williamson synthesis?
(a) CH3OCH2CH3; (b) C6H5OCH2CH3; (c) (CH3)3COCH2C6H5
Solution:(a) CH3ONa & C2H5I or C2H5ONa & CH3I; (b) Sodium phenoxide & ethyl iodide
(c) Sodium tert-butoxide & benzyl chloride.
Illustration: 3. How will you prepare 2-ethoxypropane by Williamson reaction?
Solution: C2H5Br + Na+O- CH(CH3)2 .
Illustration: 4. To prepare anisole, iodobenzene cannot be taken as the starting material. Explain why?
Solution: Due to resonance, the C – I bond acquires partial double bond character & hence is difficult
to cleave.
(a) CH3CH2OH + CH2N2 H2SO4 / Δ (A) + (B)
(b) CH3CH2CH2OH + HBr (A) + (B)
(c) CH3CH2 – Br + CH3CH2 – Br + Ag2O (A) + (B)
Solution: (a) CH3CH2OH + CH2N2 H2SO4 / Δ CH3CH2 – OCH3 + N2
(b) CH3CH2CH2OH + HBr CH3CH2CH2Br + H2O
(c) CH3CH2 – Br CH3CH2
+ Ag2 O O + 2AgBr
CH3CH2 – Br CH3CH2

6 PROPERTIES OF ETHERS
 Physical Properties of Ethers:
(a) Colour & odour: They are colourless liquids with pleasant ethereal odour.
(b) Texture: Lower members are gases or volatile liquids.
Example: CH3OCH3 & CH3OC2H5 (gases) ; C2H5OC2H5 (volatile liquid).
(c) Boiling point: There is no association through hydrogen – bonding, hence they have lower boiling points
than isomeric alcohols.
(d) Polarity: They are slightly polar but this polarity does not affect their points boiling
(e) Density: Their density is less than water & so they float on water surface.
(f) Ether vapours are highly inflammable. Ether fire is extinguished by CO 2 or pyrene (CCl4) extinguisher &
not by water since ether floats on water.
 Chemical Properties of Ethers:
Ethers are relatively inert compounds in spite of the presence of oxygen atom carrying two loan
pairs of electrons in their molecules. It is because of this reason that those are used as solvents.
They undergo chemical reactions under specific conditions. Some of the reactions of ethers are
being described as follows:
a) Cleavage of C – O bond:
Carbon oxygen bond in ethers can be cleaved by the use of reagents, like halogen acids, sulphuric
acid & phosphorous pentachloride, etc.
Cleavage with halogen acid:
Ethers can be cleaved by the use of hydrochloric acid or hydrobromic acid to give alkyl halide
& alcohol.
373 K
R–O–R + HX ROH + RX (X = Br, I)
Ether Alcohol Alkylhalide
373 K
C2H5OC2H5 + HI C2H5OH + C2H5I
In case excess of HI is used, the alcohol formed reacts further with HI to form alkyl iodide.
The overall reaction can be written as:
C2H5OC2H5 + 2HI 373 K 2C2H5I + H2O
If one group of is methyl & other group is tertiary alkyl group, the main product is methyl alcohol
& tertiary alkyl halide. It is because the departure of leaving group (CH 3 – OH) creates a more
stable tertiary carbocation.
CH3 CH3
CH3 – C – OCH3 + HI 373 K CH3 – C – I + CH3OH
Methyl alcohol
CH3 CH3
tert-Butyl methyl alcohol tert-Butyl iodide
The bond between O – CH3 is weaker than the bond between O – C6H5 because the carbon of
phenyl group is sp2 hybridised & there is a partial double bond character.
Therefore, the attack of 𝐼 − ion breaks O – CH3 bond to form CH3I.
O – CH3 OH
+ HI 373 K + CH3I
Methyl iodide
Anisole Phenol
b) Ring substitution in aromatic ethers:
The alkoxy group (– OR) attached to aromatic ring activates the ring towards electrophilic
substitution & directs the incoming electrophile to ortho & para positions:
OR + OR + OR +OR OR
I II III IV V

The presence of negative charge at ortho & para positions indicates that electron density is more
at these positions. Therefore, electrophile is likely to attack on these positions resulting in the
formation of ortho & para substituted products.
H2SO4 / 413K
(i) C2H5OH + C2H5OH (A)
(ii) C2H5Br + C2H5ONa (A) + (B)
373K
(iii) C2H5OC2H5 + HI (A) + (B)
373K
(iv) C2H5OC2H5 + 2HI (A) + (B)
O2 / light
(v) CH3CH2OCH2CH3 (A)
(vi) C2H5OC2H5 + 10Cl2 (A) + (B)
(vii) OCH3
CS2
+ Br2 (A) + (B)
(viii) OCH3
HNO3
(A) + (B)
H2SO4
(ix) OCH3
AlCl3
+ CH3Cl (A) + (B)
Solution: (i) C2H5OH + C2H5OH C2H5OC2H5

(ii) C2H5Br + C2H5ONa C2H5OC2H5 + NaBr
373K
(iii) C2H5OC2H5 + HI C2H5OH + C2H5I
373K
(iv) C2H5OC2H5 + 2HI 2C2H5I + H2O
O2 / light
(v) CH3CH2OCH2CH3 CH3CH – O – CH2CH3
O–O–H
1-Ethoxy ethyl hydroperoxide
(vi) CH3CH2OCH2CH3 + 10Cl2 CCl3CCl2OCCl2CCl3 + 10HCl
Perchlorodiethyl ether
(vii) OCH3 OCH3 OCH3
Br
CS2
+ Br2 +
2-Bromomethoxy Br
benzene 4-Bromomethoxy
benzene
(viii) OCH3 OCH3 OCH3
NO2
HNO3 +
H2SO4
NO2
(ix) OCH3 OCH3 OCH3
CH3
CS2
+ CH3Cl +
CH3

LCOHOLS
Introduction: These are hydroxyl derivatives of aliphatic hydrocarbons and can be monohydric,
dihydric or polyhydric based on the number of – OH groups.
General formula: CnH2n+1OH,
General representation: R – OH
Classification on the Basis of Number of –OH Groups
 Monohydric alcohols: Those alcohols which contain only one –OH group in their molecule are called
monohydric alcohols, CnH2n+1OH.
E.g., CH3OH, C2H5OH, etc.
 Dihydric alcohols: Those alcohols which contain two –OH groups in their molecule are called
dihydric alcohols, CnH2n(OH)2.
E.g., CH2 – OH = Ethanediol.
CH2 – OH
 Trihydric alcohols: Those alcohols which contain three –OH groups in their molecule are called
trihydric alcohols, CnH2n – 1(OH)3.
CH2 – OH = Propanetriol.
E.g., CH2 – OH
CH2 – OH
Classification on the Basis of Nature of C – OH Groups
 Primary alcohols: Monohydric alcohols in which the –OH group is attached to a primary (10) carbon
atom are known as primary alcohols.
E.g., CH3OH, CH3CH2OH, etc.
 Secondary alcohols: Monohydric alcohols in which the –OH group is attached to a secondary (20)
carbon atom are known as secondary alcohols.
E.g., CH3 – CH – CH3 , CH3 – CH – CH2 – CH3 etc.
OH OH
 Tertiary alcohols: Monohydric alcohols in which the –OH group is attached to a tertiary (30) carbon
atom are known as secondary alcohols.
CH3
E.g., CH3 – C – OH , etc
CH3
 Lower members are colourless toxic liquids, whereas the higher members are waxy solids.
 The boiling point of alcohol is always higher than the corresponding ether, hydrocarbon
and haloalkanes due to the presence of hydrogen bonding.
 Boiling point ∝ number of CH group.2
 It may be noted that as the size of the group R increases, the rate of esterification
reaction decreases due to steric hindrance. Thus, the order of reactivity of alcohols
follows the sequence: CH3OH > CH3CH2OH > (CH3)2CHOH > (CH3)2COH and that of the
acids follows the sequence: HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH.

A A
Hydration of alkenes Na
H2O/H+ RONa + H2
RCH = CH2
(Hydration) RCOOH
L L RCOOR + H2O
Hydroboration oxidation
RCOCl
B2H6 /H2O2 , OH–
RCOOR + HCl
RCH = CH2
(RCO)2O
Oxymercuration reduction RCOOR + RCOOH
C C
(i) Hg(OAc) ; H2O
RCH = CH2 R’MgX
(ii) NaBH4 R’H + Mg(OR)X
Grignard Reagent HX
(i) RMgX RX + H2O
C=O
PX3
(ii) H2O/H+
O O RX + H2O
From aliphatic primary amines PCl5
RNH2 + HONO RCl + POCl3 + HCl
From haloalkanes SOCl5

RCl + SO2 + HCl
R – X + KOH(aq) H H
Conc. H2SO4 /443K
From carbonyl compounds RCH = CH2 + H2O
Conc. H2SO4 /413K

H2 / Ni or, LiAlH4
ROR+ H2O
RCH = CH2
O O K2Cr2O7 / H+
H2 / Ni R – COOH
R2C = O –
Or KMnO4 / OH
LiAlH4 Cu / 573K
RCOOH RCHO or RCOR or alkene
L L (from 10 (from 20 (from 30
alcohol) alcohol) alcohol)
LiAlH4
RCOOR’ PCC
RCHO
Or CrO3.C5H5N.HCl
NaOH / Δ
RCOOR’ S S
VENTOLIN INHALERS: (A quick relief from breathlessness) Asthma

DO YOU patients use ventolin inhalers which give quick relief from breathlessness
caused due to asthma. These ventolin inhalers contain salbutamol which has
KNOW a structure similar to adrenaline & hence, works as a bronchodilator.

HENOLS
 Phenols are derivatives of benzene in which a ring hydrogen atom is replaced by –OH group. They
possess the general formula Ar – OH where Ar is a phenyl or a substituted phenyl group.
 In phenols the –OH group is directly attached to the carbon atom of the ring.
E.g., OH OH OH OH OH
Br
Br CH3
Phenol 2-Bromophenol 3-Bromophenol m-Cresol CH3
(o-Bromophenol) (m-Bromophenol) (3-methylphenol) p-Cresol
(4-methylphenol)
 Like alcohols, phenols can also be classified as monohydric, dihydric, trihydric or polyhydric according
to their molecules containing one, two, three, or more hydroxyl groups respectively.
E.g., OH OH OH
OH OH
OH
Phenol (Catechol) 3-Bromophenol
(Monohydric) (1,2-Dihydroxybenzene) (1,2,3-Trihydroxybenzene)
(dihydric) (trihydric)
 Alcohols are high boiling point liquid due to the presence of intermolecular hydrogen bond
between molecules which require extra energy to break this bond so boiling point is high.
 Their boiling point order is P > S > T, because on increasing number of branches, compound
acquire spherical shape which is least in area so require less energy for evaporation.
Boiling point ∝ surface area.
 On increasing number of carbon atoms in same type of alcohol i.e., on increasing molecular
mass, boiling point increases.
Boiling point ∝ molecular mass.
 Alcohols are completely soluble in water due to formation of hydrogen bond with water
molecule. Their solubility is inversely proportional to size and molecular mass.
 Boiling point of alcohol is lower than that of carboxylic acid because two molecules of
carboxylic acid form a cyclic structure known as dimer which require more energy to break
cyclic structure than alcohol.
 Boiling point of alcohol is higher than aldehyde, ketone, ether and haloalkanes, because
alcohol molecules are attached by intermolecular hydrogen bond while others are attached
by dipole – dipole attraction and decreasing orders of boiling point is:
R – COOH > R – OH > R – CHO > R – CO – R > R – O – R > R – X.
 In Williamson synthesis, 3
0
0
alkoxide and 10 alkyl halide should be used to prepare 30 ether.
If we used 3 alkyl halide then elimination take place and alkene is formed.
 Phenol is more acidic than alcohol because phenoxide ion is more stable due to resonance
stabilisation so its respective H+ is more reactive.
 Phenol form violet colour with FeCl solution but alcohols does not form any colour so it is
3
used as distinguish test between alcohol and phenol.
 Alcohols are acidic in nature and their acidic nature order is P > S > T.

P P Tests of Phenol
Ferric chloride test:
From benzene sulphonic acid
Phenol gives violet colour with neutral
SO3Na
NaOH (fusion)
FeCl3 solution.
OH
H2O / H+
H H
6 + FeCl3 3H+ + [Fe(OC6H5)6]3– + HCl
From diazonium salts (violet complex)
N2+ C𝑙 −
H2O / ∆ Bromide water test:
Phenol gives white ppt. with Br2 – water
E E due to the formation of
2,4,6- tribromophenol
From Grignard reagent
OH OH
MgBr Br Br
(i) 1/2 O2 H2O
+ 3Br2 +HBr
(ii) H+/ H2O N N
Br (White ppt.)
Rachig’s process ACIDITY OF PHENOLS
Cl a) Phenols are acidic due to resonance
stabilization of its conjugate base
CuCl2/FeCl3 +H2O
(phenoxide ion).
+ HCl + ½ O2
500K 4250C O O b) Carboxylic acids > Phenols > Water >
Alcohols.
c) An acid can be deprotonated by a base that
Dow’s process has a conjugate acid with a higher𝑝𝐾𝑎 .
Cl OH 𝑂−
3000C / High pressure
+ OH − + H2O
+ 2NaOH
Dil. HCl
L L
𝑝𝐾𝑎 = 10 15.7
From Cumene
OH
CH3
C–H Air [O] + 𝐻𝐶𝑂3− No reaction.
CH3
H2O / H+ H2CO3 (𝑝𝐾𝑎 = 6.4 is a stronger acid than phenol)
S S d) Electron withdrawing groups (EWG) s
By decarboxylation of stabilize the phenoxide ion & hence
Sodium salicylate increase acidity of phenols.
Cl 𝑂−
COONa (−NO2 , −X, −CN, −COOH, etc)
CaO, Δ
+ 2NaOH
EWG
DO YOU PHENOL: Phenols can be prepared: from Coaltar (middle oil fraction).
KNOW Phenol can give Lederer-Manasse chemical reaction  Bakelite.

OK OK Cl OK OH OK
CH CH CHO
KOH CHCl3 Cl 2KOH OH
– H2O –HCl –2KCl – H2O
–2KCl
2KOH
Reimer – Tiemann Reaction OH
CHO
Salicylaldehyde
ONa ONa OH OH
COONa COOH
NaOH CO2 Rearrangement HCl
– H2O – NaCl
Sod. Phenoxide Sod. Salicylate Salicylic acid

Kolbe Reaction
FeCl3
[(C6H5O)6Fe]−3 + 3HCl + 3H + Distinguish Test For Phenol
OH
Br Br
3Br – Br 2, 4, 6 – Tribromo phenol

Bromine water
– 3HBr
Br
C6H5OH OH
Or NO2 NO2
OH
3HNO3 2, Picric Acid
(Fuming)
H2SO4
NO2
OH
Br
2Br2 + OH Br Halogenation
CS2 or CCl4
– 2HBr
o-Bromo phenol p-Bromo phenol
OH
NO2
2HNO3 (dil.) + OH NO2 Nitration
H2SO4
– 2H2O
o-Nitro phenol p-Nitro phenol
OH
SO3H
2H2SO4 (dil.) + OH SO3H Sulphonation
– 2H2O
o-hydroxy benzene p-hydroxy benzene

sulphonic acid sulphonic acid
OH
CH3
2CH3 – Cl + OH CH3 Friedel Craft alkylation
AlCl3
– 2HCl
o-Cresol p-Cresol

THERS
General formula: CnH2n + 2O
General representation: R – O – R’
Classification of Ethers
 Aliphatic ethers: These are those ethers in which both R & R’ are alkyl groups
E.g., CH3 – O – CH3 (dimethyl ether); CH3 – O – C2H5 (ethyl methyl ether).
 Aromatic ethers: These are those ethers in which either one or both R & R’ groups are aryl groups.
E.g., C6H5 – O – CH3 (methyl phenyl ether); C6H5 – O – C6H5 (diphenyl ether).

 E E

Bydehydration of alcohols Reaction of Loan Pair of Oxygen
 ConcH2SO4 H+ R
 ROH + HOR O+ – H
 413K (Acids) R

 Al2O3 T T
 R BF3 R
ROH + HOR
 633K
O O BF3
 R (Lewis Acids) R
Boron-trifluoride etherate
 HBF4
ROH + CH2N2 H+ R
O O
From alkyl halides H H (Acids) R
Δ Peroxide
2R – X + Ag2O
Reaction of Loan Pair of Oxygen
Δ PCl5
R – X + RONa 2R – Cl + POCl3
(Acids)
Preparation of cyclic ether E E
R Conc. H2SO4
(or Epoxides)
O 2ROH
Ag CH2 R H2O
CH2 = CH2 + ½ O2 O
200 – 4000C CH2 HX
R
R R (Excess)
 Aromatic ethers may further be classified as:

 Alkyl-aryl ethers or phenolic ethers: In this type of ethers one group is alkyl & the other group is
aryl.
 Diaryl ethers: In this type of ethers both the groups are aryl.
 Symmetrical ethers: These are those ethers in which both R & R’ are same. They are also called
H5 O
simple ethers. E.g., CH3 – O – CH3 ; C6H5 – O – C6O
 Unsymmetrical ethers: In such ethers both R & R’ groups are different. They are also called mixed
ethers. E.g., CH3 – O – CH2CH3 ; CH3 – O – C6H5
William Thomas Green Mortan (August 9, 1819 – july 15, 1868)
‘Ether Day’, Friday 16 October 1846 marks the first
DO YOU successful demonstration of the inhalation of ether
L a means
vapour as L of overcoming pain of surgery by
KNOW dentist William T. G. Morton at the Massachusetts
General Hospital in Boston USA.
37 For More Notes WhatsApp Us On 7780819690 , 9596948590

S
Page number
V (A S
1. Classify the following as primary, secondary and tertiary alcohols:

CH3
(a) CH3 – C – CH2 – OH (b) H2C = CH – CH2OH (c) CH3 – CH2 – CH2 – OH
CH3
(d) OH (e) CH2 – CH – CH3 (f) CH3
CH – CH3 OH CH2 = CH – C – OH
CH3
Ans: Primary alcohol  (a), (b), (c)

Secondary alcohol  (d), (e)
Tertiary alcohol  (f)
2. Identify allylic alcohols in the above examples.
Ans: Allylic that means C = C – C – OH
The alcohols given in (b) and (f) are allylic alcohols.
3. Name the following compounds according to IUPAC system.
CH2Cl CH3 HO CH2OH OH
(a) CH3 – CH2 – CH – CH – CH - CH3 (b) H3C – CH – CH2 – CH – CH – CH3 (c)
CH2OH CH3
(d) H2C = CH – CH – CH2 – CH2 – CH3 (e) CH3 – C = C – CH2OH Br
OH CH3 Br
Ans: (a) 3 − Chloromethyl − 2 − isopropylpentan − 1 − ol
(b) 2,5 − Dimethylhexane − 1,3 − diol
(c) 3 − Bromocyclohexanol
(d) Hex − 1 − en − 3 − ol
(e) 2 − Bromo − 3 − methylbut − 2 − en − 1 − ol
4. Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on
methanal?
(a) CH3 – CH – CH2OH (b) CH2OH
CH3
δΘ δ⨁
𝐻2 𝑂
Ans: (a) H – C – H + CH3 – CH – MgBr H – CH – CH – CH3 CH2 – CH – CH3
O CH3 BrMgO CH3 HO CH3
MgBr CH2OMgBr CH2OH
𝐻2 𝑂
(b) H – C – H + + Mg(OH)Br
O
Methanal Cyclohexylmagnesium Cyclohexylmethanol
Bromide
5. Write structures of the products of the following reactions:
O O
𝑁𝑎𝐵𝐻4 /𝐻⨁
(a) CH2 − C = O − CH3

𝑁𝑎𝐵𝐻4
(b) CH3 − CH2 − CH − CHO
CH3
O O OH
Ans (a) CH2 − C = O − CH3 CH2 − C − OCH3
𝑁𝑎𝐵𝐻4 /𝐻⨁
O
Methyl (2-oxocyclohexyl) ethanoate Methyl (2-hydroxycyclohexyl) ethanoate

𝑁𝑎𝐵𝐻4
(b) CH3 − CH2 − CH − CHO CH3 – CH2 – CH – CH2OH
CH3 CH3
2-Methylbutanal 2-Methylbutan-1-ol
6. Give structures of the products you would expect when each of the following alcohol reacts with:
(a) HCl – ZnCl2 (b) HBr (c) SOCl2
(i) Butan – 1 – ol (ii) 2 – Methylbutan – 2 – ol
Cl
𝐻𝐶𝑙 + 𝑍𝑛𝐶𝑙2
Ans: (a) (i) CH3 – CH2 – CH2 – CH2 – OH CH3 – CH2 – CH – CH3
Butan–1–ol
OH Cl
𝐻𝐶𝑙 + 𝑍𝑛𝐶𝑙2
(ii) CH3 − CH2 − C − CH3 CH3 – CH2 – C – CH3 + H2O
CH3 CH3
2-Methylbutan-2-ol (30) 2-Chloro-2-methylbutane (White turbidity)
Tertiary alcohols react immediately with Luca’s reagent.
Br
−𝐻2 𝑂
(b) (i) CH3 – CH2 – CH2 – CH2 – OH + HBr CH3 – CH2 – CH – CH3
Butan–1–ol
OH Br
(ii) CH3 − CH2 − C − CH3 + HBr CH3 – CH2 – C – CH3 + H2O
CH3 CH3
2-Methylbutan-2-o 2-Bromo-2-methylbutane
(c) (i) CH3 – CH2 – CH2 – CH2 – OH + SOCl2 CH3 – CH2 – CH2 – CH2Cl + HCl
Butan–1–ol 1-Chlorobutane
OH Br
(ii) CH3 − CH2 − C − CH3 + SOCl2 CH3 – CH2 – C – CH3 + SO2 + HCl
CH3 CH3
2-Methylbutan-2-ol 2-Chloro-2-methylbutane
7. Predict the major product of acid catalysed dehydration of:
(a) Butan – 1 – ol
(b) 1 – Methylcyclohexanol
𝐷𝑒ℎ𝑦𝑑𝑟𝑎𝑡𝑖𝑜𝑛
Ans: (a) CH3 – CH2 – CH2 – CH2 – OH CH3 – CH = CH – CH3 + H2O
Butan–1–ol 𝐻+ But-2-ene
(Major product)
HO CH3 CH3
(b)
𝐷𝑒ℎ𝑦𝑑𝑟𝑎𝑡𝑖𝑜𝑛
+ H2O
𝐻+
1-Methylcyclohexanol 1-Methylcyclohexene (Major product)

8. Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the
corresponding phenoxide ions.
O O O O O
Ans:
(Resonance structure of the phenoxide ion)

O O O O O O
N+ N+ N+ N+ N+ N+
O− O O− O O− O O− O− O− O O− O
(Resonance structure of 𝑝 − 𝑛itrophenoxide ion)
O O O O O O O O O O
+ + + +
N N N N N
O O O O O−
(Resonance structure of 𝑝 − 𝑛itrophenoxide ion)

9. Write the equations involved in the following reactions:
(a) Reimer – Tiemann reaction
(b) Kolbe’s reaction.
Ans: (a) OH OH
CHO
𝐶𝐻𝐶𝑙3 + 𝐴𝑙𝑐. 𝑁𝑎𝑂𝐻
Phenol (Salicylaldehyde)
(b) OH OH
CHO
(𝑖) 𝑁𝑎𝑂𝐻 + 𝐶𝑂2
(𝑖𝑖) 𝐻 +
10. Write the reactions of Williamson synthesis of 2 – Ethoxy – 3 – methylpentane starting from Ethanol
and 3 – Methylpentan – 2 – ol.
HBr
Ans: C2. H5 OH C2H5Br
Ethanol Bromoethane
H3C OH H 3C CH3
Na
CH3 – CH2 – CH – CH – CH3 CH3 – CH2 – CH – CH – ONa
3-Methylpentan-2-ol Sodium-3-Methylpentan-2-oxide
H3C CH3 H3C CH3
CH3 – CH2 – CH – CH – ONa + C2H5Br CH3 – CH2 – CH – CH – OC2H5 + NaBr
2-Ethoxy-3-methylpentane

11. Which of the following is an appropriate set of reactants for the preparation of
1 – Methoxy – 4 – nitrobenzene and why?
Br ONa
(a) (b)
+ CH3ONa + CH3Br
Ans: (Set – b) is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene.

Br OCH3
1
6 2
+ CH3Br \ + NaBr
5 3
6
\ 4
NO2 6 NO2
1-Methoxy-4-nitrobenzene
(Set – a) Bromine atom is stable by resonance.
12. Predict the products of the following reactions:
(a) CH3 – CH2 – CH2 – O – CH3 + HBr
OC2H5
(b) + HBr
OC2H5 Conc. 𝐻2 𝑆𝑂4

(c)
Conc. 𝐻𝑁𝑂3
HI
(d) (CH3)3 – C – OC2H5
Ans: (a) CH3 – CH2 – CH2 – O – CH3 + HBr CH3 – CH2 – CH2 – OH + CH3 – Br (SN2)
𝑛 − Propylmethyl ether Propanol Bromomethane
OC2H5 OH
(b) + HBr + C2H5Br (SN2)
Bromoethane
Ethoxybenzene Phenol
OC2H5 OC2H5 OC2H5
Conc. 𝐻2 𝑆𝑂4
(c) +
Conc. 𝐻𝑁𝑂3 NO2 NO2
Ethoxybenzene 1-Ethoxy-4-nitrobenzene 2-Ethoxynitrobenzene
(Major product) (Minor product)
HI
(d) (CH3)3 – C – OC2H5 (CH3)3C – I + C2H5OH (SN1)
tert-Butylethyl ether tert-Butyliodide Ethanol
13. Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that
of ethanol.
Ans: The acidic nature of phenol can be represented by the following two reactions.
(a) Phenol reacts with sodium to give sodium phenoxide, liberating H 2.
OH ONa
1
+ Na + 2 H2
Phenol Sodium phenoxide

(b) Phenol reacts with sodium hydroxide to give sodium phenoxide and water as by-product.

OH ONa
+ NaOH + H2 O
Phenol Sodium phenoxide
The acidity of phenol is more than that of ethanol. This is because after losing a proton,
the phenoxide ion undergoes resonance and gets stabilized whereas ethoxide ion does not.
O O O O O
14. Explain why ortho-nitro phenol is more acidic than ortho-methoxy phenol?
Ans: Electron withdrawing effect of nitro group and electron releasing effect of methoxy group.
15. Explain how does the – OH group attached to a carbon of benzene ring activates it towards
Electrophilic substitution?
Ans: Electron density at 𝑜 − and 𝑝 − 𝑝osition increases and thus the electrophile attacks easily.
⨁ ⨁ ⨁
O–H O–H O–H O–H O–H
16. Explain the following with an example:

(a) Williamson ether synthesis
(b) Unsymmetrical ether
Ans: Williamson ether synthesis is a laboratory method to prepare symmetrical and
unsymmetrical ethers by allowing alkyl halides to react with sodium alkoxide.
R–X + R’ – O Na R – O – R’ + NaX
Alkyl halide Sodium alkoxide Ether
This reaction involves SN2 attack of the alkoxide ion on the alkyl halide. Better results
are obtained in case of primary alkyl halides.
CH3 – CH – O Na+ + CH3 – Br CH3 – O – CH – CH3 + NaBr
CH3 CH3
If the alkyl halide is secondary or tertiary, then elimination competes over substitution.
17. Give reason for the higher boiling point of ethanol in comparison to methoxymethane.
Ans: Ethanol undergoes intermolecular H-bonding due to the presence of –OH group, resulting
in the association of molecules. On the other hand, methoxymethane does not undergoes
H-bonding. Hence, the boiling point of ethanol is higher than that of methoxymethane.
18. Illustrate with examples the limitations of Williamson synthesis for the preparation of certain
types of ethers.
Ans: The reaction of Williamson synthesis involves S N2 attack of an alkoxide ion on a primary
alkyl halide.
H3C CH3
CH3 – C – O− Na+ + CH3 – Cl CH3 – O – C – CH3 + NaCl
δ+ δ−
CH3 CH3

But if secondary or tertiary alkyl halides are taken in place of primary alkyl halides, then
elimination would compete over substitution as a result, alkenes would be produced.
This is because alkoxides are nucleophiles as well as strong bases. Hence, they react with
alkyl halides, which results in an elimination reaction.
H3C CH3
CH3 – C – Cl + NaO – CH3 CH3 – C = CH2 + CH3OH + NaCl
CH3 Alkene
Tert-Alkyl halide
19. How is 1 − Propoxypropane synthesised from propan −1 − ol? Write mechanism of this reaction.
Ans: 2CH3CH2CH2 – OH 𝐻+ CH3CH2CH2 – O – CH2CH2CH3
Propan-1-ol 1-Propoxypropane
The mechanism of this reaction involves the following three steps:
Step 1: Protonation
H
𝐻+
CH3CH2CH2 – O – H CH3CH2CH2 – O+ – H
Propan-1-ol
Step 2: Nucleophilic attack
H
+
CH3CH2CH2 – O + CH3 – CH2 – CH2 − O CH3CH2CH2 − O+ − CH2CH2CH3 + H2O
H H H
Step 3: Deprotonation
CH3CH2CH2 − O+ − CH2CH2CH3 CH3CH2CH2 – O – CH2CH2CH3 + H +
H 1-Propoxypropane
20. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method.
Give reason.
Ans: The formation of ethers by dehydration of alcohol is a bimolecular reaction (S N2) involving
the attack of an alcohol molecule on a protonated alcohol molecule. In this method, the alkyl
group should be unhindered. In case of secondary or tertiary alcohols, the alkyl group is
hindered. As a result, elimination dominates substitution. Hence, in place of ethers, alkenes
are formed.
21. Write the equation of the reaction of hydrogen iodide with:
(a) 1 − Propoxypropane
(b) Methoxybenzene
(c) Benzyl ethyl ether
HI
Ans: (a) C2H5CH2 – O – CH2C2H5 + HI CH3CH2CH2 – OH + CH3CH2CH2 – I
1-Propoxypropane Propan-1-ol 1-Iodopropane
OCH3 ONa
(b) + HI + CH3 – I (SN2)
Methoxy benzene Phenol

CH2 – O – C2H5 CH2I
(c) + HI + C2H5 – OH (SN1)

Ethanol
Benzyl ethyl ether Benzyl iodide

Multiple Choice Questions:

1. The correct IUPAC name of the organic compound
CH3 – CH – CH – CH – CH2 OH is
Cl CH3 CH3
(a) 4-chloro-2,3-dimethylpentan-1-ol
(b) 2-chloro-3,4-dimethylpentane-5-ol
(c) 2,3-dimethyl-4-chloropentan-1-ol
(d) 2-chloro-3,4-dimethyl n-pentyl alcohol
(e) 2,3-dimethyl-4-chloro n-pentyl alcohol (Kerala PMT)
2. Vinyl carbinol is
(a) OH – CH2 – CH = CH2
(b) CH3 C (OH) = CH2
(c) CH3 – CH = CH – OH
(d) CH3 – C (CH2OH) = CH2 (AFMC)
3. Correct configuration of the following is
CH3
H OH
CH3 OH
H
(a) 1S, 2S
(b) 1S, 2R
(c) 1R, 2S
(d) 1R, SR (AFMC)
4. The reaction
Me
– +
– OH NaOH – O Na Me-I j –O can be classified as
(a) dehydration reaction

(b) Williamson alcohol synthesis reaction
(c) Williamson ether synthesis reaction
(d) alcohol formation reaction (NEET Phase – I)
5. Assertion: Phenol is more acidic than ethanol.
Reason: Phenoxide ion is resonance stabilised.
(a) If both assertion & reason are true & reason is the correct explanation of assertion.
(b) If both assertion & reason are true but reason is not the correct explanation of assertion.
(c) If assertion is true but reason is false.
(d) If both assertion & reason are false. (AIIMS)
6. The reaction which involves dichlorocarbene as an electrophile is
(a) Reimer-Tiemann reaction
(b) Kolbe’s reaction
(c) Friedel-Craft’s acylation
(d) Fitting’s reaction (Karnataka CET)

7. Reaction of phenol with chloroform in presence of dilute sodium hydroxide finally introduces which one of
the following functional group?
(a) –COOH
(b) –CHCl2
(c) –CHO
(d) –CH2Cl (AIPMT)
8. Dehydration of which one of the following alcohols produces an alkene exhibiting cis-trans isomerism?
(a) Iso-propyl alcohol
(b) Tertiary butyl alcohol
(c) n-Butyl alcohol
(d) Neopentyl alcohol
(e) 3-Pentanol (Kerala PMT)
9. During the dehydration of alcohols to alkenes by heating with conc. H 2SO4, the initiating step is
(a) elimination of water
(b) protonation of an alcohol molecule
(c) formation of an ester
(d) formation of carbocation (AIIMS)
10. What reagent(s) can be used to convert: 2-Methylpentan-1-ol into 2-methylpentanal?
(a) Na2Cr2O7
(b) LiAlH4
(c) CrO3 - Pyridine
(d) KMnO4 (AMU (Med.))
11. Prene, CH3 CH = CH2 can be converted into 1-propanol by oxidation. Indicate which set of reagent
amongst the following is ideal for the above conversion.
(a) KMnO4 (alkaline)
(b) Osmium tetroxide (OsO4/CH2Cl2)
(c) B2H6 & alk. H2O2
(d) O3/Zn (JIPMER)
12. OH
C6H5COCl/base X Nitration Y (Major product)
Y is
(a) h – COO – H – NO2
(b) HO – – COO – – NO2
(c) O2N – – COO–
(d) O2N – – COO – j – NO2

(Karnataka CET)

13. Phenol is distilled with Zn dust followed by Friedel-Crafts alkylation with propyl chloride in the presence
of AlCl3 to give a compound (B). (B) is oxidised in the presence of air to form the compound (C).
The structural formula of (C) is
(a) COOH
OH
(b) H3C
C–O–O–H
H3C
(c) CH3
H3C – C – O – O – H
OH
(d) COOH
(NEET Karnataka)
14. Salicylic acid can be easily prepared by reaction between
(a) phenol & CO2
(b) benzoic acid & H2O2
(c) benzene diazonium chloride & CO2
(d) phenol & formic acid (AIIMS)
15. Phenol on treatment with conc. HNO3 gives
(a) o-nitrophenol
(b) p-nitrophenol
(c) o- & p-nitrophenol
(d) 2,4,6-trinitrophenol (J & K CET, OJEE 2010)
16. Correct the statement(s) in case of n-butanol & t-butanol is (are)
(a) both are having equal solubility in water
(b) t-butanol is more soluble in water than n-butanol
(c) boiling point of t-butanol is lower than n-butanol
(d) boiling point of n-butanol is lower than t-butanol (WB JEE)
17. Primary, secondary & tertiary alcohols can be distinguished by
(a) Borsche’s test
(b) Lucas test
(c) Hinsberg’s test
(d) Tollen’s test
(e) Fehling’s test (Kerala PMT)

18. Assertion: Dehydration of alcohols always takes place in basic medium

Reason: OH– is a better leaving group.
19. The best method to prepare 3-methylbutan-2-ol from 3-methylbut-1-ene is
(a) addition of water in the presence of dil. H2SO4
(b) addition of HCl followed by reaction with dil. NaOH (aq)
(c) hydrobromination-oxidation reaction
(d) oxymercuration-demercuration reaction (BHU)
20. The correct order of decreasing acidity of nitrophenols will be
(a) m-nitrophenol > p-nitrophenol > o-nitrophenol
(b) o-nitrophenol > m-nitrophenol > p-nitrophenol
(c) p-nitrophenol > m-nitrophenol > o-nitrophenol
(d) p-nitrophenol > o-nitrophenol > m-nitrophenol (WB JEE)
21. Which one of the following compounds has the most acidic nature?
(a) – CH2OH
(b) – OH
(c) – OH
OH
(d) – CH –
(AIPMT)
22. OH OH
CHCl3 + NaOH CHO
H+
This reaction is named as

(b) Kolbe’s preparation
(c) Cannizzaro reaction
(d) Aldol condensation (BHU)
23. Aspirin, an antipyretic drug is chemically
(a) methyl salicylate
(b) ethyl salicylate
(c) acetylsalicylic acid
(d) o-hydroxybenzoic acid (UP CPMT)

24. Cl
A (C10H18O) HCl H3C – C – CH3
Cl CH3
Degree of unsaturation of A = 2, it contains no double or triple bond.
(a) OH
H3C – C – CH3
(b) OH
H3C – C – CH3
(c) H3C – CH – CH2OH
(d) None of these. (AIIMS)

25. Cumene process is the most important commercial method for the manufacture of phenol. Cumene is
(a) iso-propyl benzene
(b) ethyl benzene
(c) vinyl benzene
(d) propyl benzene (AIIMS)
26. Which one of the following is correctly written?
(a) OH OH
Br Br
+ Br2 (water)
CH3 CH3
Br
(b) OH OH
+ Br2 (water)
CH3 CH2Br
(c) OH OBr
+ Br2 (water)
CH3 CH3
(d) OH
CH3
+ Br2 (water)
CH3 Br
OH (AMU (Med.))

27. OH
+ CH2I2 + NaOH
OH
The product is
(a) O
O
(b)
O
(c) OCH3
OH
(d) CH2I
ONa (OJEE)
28. On reacting with neutral ferric chloride, phenol gives
(a) red colour
(b) blue colour
(c) violet colour
(d) green colour (J & K CET)
29. 4-Methoxyacetophenone can be prepared from anisole by
(b) Kolbe’s reaction
(c) Friedel-Crafts reaction
(d) Wurtz reaction
(e) Cannizzaro reaction (Kerala PMT)
30. O
HI (excess)/Δ
O
(a) OH
OH + CH2I2
(b) I
+ HCHO
CH2 – I
(c) OH
+ I – CH2 – OH
CH2 – I
(d) I
OH + I2 + CH3OH
(AIIMS)

31. Which one of the following methods is used to prepare Me3COEt with a good yield?
(a) Mixing EtONa with Me3CCl
(b) Mixing M3CONa with EtCl
(c) Heating a mixture of (1 : 1) EtOH & Me3COH in presence of conc. H2SO4
(d) Treatment of Me3COH with EtMgI. (WB JEE)
32. Assertion: Rate of reaction of alkyl halide in williamson’s synthesis reaction is 10 RX > 20RX > 30RX.
Reason: It is a type of bio-molecular substitution reaction (SN2).
33. Which of the following ether is unlikely to be cleaved by hot conc. HBr?
(a) h–O–
(b) h–O–
(c) h–O–
(d) h – O – CH2 – (AMU (Med.))
34. Formation of methyl tertiary butyl ether by the reaction of sodium tertiary butoxide & methyl bromide
involves
(a) elimination reaction
(b) electrophilic addition reaction
(c) nucleophilic addition reaction
(d) nucleophilic substitution reaction (J & K CET)
35. One mole of an organic compound A with the formula C 3H8O reacts completely with two moles of HI to
form X & Y. When Y is boiled with aqueous alkali it forms Z. Z answers the iodoform test.
The compound A is
(a) propan-2-ol
(b) propan-1-ol
(c) ethoxyethane
(d) methoxyethane (Karnataka CET)
36. Assertion: Ethers behave as bases in the presence of mineral acids.
Reason: It is due to the presence of loan pair electrons on the oxygen.

37. Anisole (CH3)3CCl/AlCl3 Cl2/FeCl3 HBr/Δ X

The product X in the above series of reaction is
(a) OCH3
Br
C(CH3)3
(b) Br
Cl
C(CH3)3
(c) Br
Br
C(CH3)3
(d) OH
Cl
C(CH3)3
(e) OCH3
Cl
C(CH3)3 (Kerala PMT)

38. Ethanol & dimethyl ether have same empirical formula but ethanol has higher boiling point due to
(a) ionic bond
(b) acidic bond
(c) hydrogen bond
(d) covalent bond (BHU)
39. Ether on reacting with P2S5 form
(a) diethyl sulphide
(b) thioalcohol
(c) thioether
(d) thioaldehyde (UP CPMT)
40. Which one of the following alcohol is used as an antifreeze reagent for marking explosive?
(a) Glycerol
(b) Glycol
(c) Ethanol
(d) Phenol (J & K CET)
41. Power alcohol is a mixture of
(a) 80% Petrol + 20% Benzene + Small quantity of Ethanol
(b) 80% Petrol + 20% Ethanol + Small quantity of Benzene
(c) 80% Ethanol + 20% Benzene + Small quantity of Petrol
(d) 50% Petrol + 50% Ethanol + Small quantity of Benzene. (Karnataka CET)

42. Dehydration of alcohol is an example of which type of reaction?

(a) Substitution
(b) Elimination
(c) Addition
(d) Rearrangement (J & K CET)
43. An oxygen containing organic compound upon oxidation forms a carboxylic acid as the only organic
product with its molecular mass higher by 14 units. The organic compound is
(a) an aldehyde
(b) a primary alcohol
(c) a secondary alcohol
(d) a ketone (Karnataka CET)
44. End product (A) of the following sequence of reactions is
OH
H2SO4/Δ (i) m-chloroperbenzoic acid A
(ii) H3O+
(a) Cl
C
Cl
(b) OH
OH
(c) OH
OH
(d)
O
(AMU (Med.))
45. The following alcohol after treatment with acid gives compound A. Ozonolysis of A gives
nonane-2,8-dione. The compound A is
CHOHMe
H+ A
Me
(a)
(b)
(c)
(d)
(J & K CET)

46. Predict the product.

OH
1. PBr3
2. Alc. KOH
(a)
(b) OH
OH
(c) Br
(d)
(OJEE)
47. OH
Dil. HNO3 A (Major product)
A is
(a) OH
NO2
(b) OH
NO2
(c) OH
NO
NO2
(d) OH
NO2 (AIIMS)

48. The correct decreasing order of pKa is

OH OH OH OH
OCH3 Cl
CH3 NO2
(I) (II) (III) (IV)
(a) II > IV > I > III
(b) IV > II > III > I
(c) III > II > IV > I
(d) IV > I > II > III (AIIMS)
49. OH
+ NH3 Anhyd. ZnCl2 /3000 C
(a) NH
(b) NO
(c) NO2
(d) NHOH
(UP CPMT)
50.
– O – CH3 HI P+Q
P & Q are
(a)
– OH + CH3I
(b)
– I + CH3OH
(c)
– CH2OH + CH3I
(d)
– I + CH3 – O – CH3
(BHU)

1. (a)
2. (a) HO – CH2 – CH = CH2
Vinyl
3. (a) CH3
1
H OH
2
CH3 OH
H
Following the procedure outlined under ‘Golden Rule’ the absolute configuration is 1S, 2S.
4. (c) Williamson’s ether synthesis reaction involves the treatment of sodium alkoxide with a suitable alkyl
halide to form an ether.
5. (a)
6. (a) OH ONa OH
CHO CHO
+ CHCl3 NaOH, 340K dil. HCl
– NaCl, – H2O – NaCl
2-Hydroxy benzaldehyde
7. (c) This is Reimer-Tiemann reaction
OH ONa OH
CHO CHO
+ CHCl3 NaOH, 340K HCl
– NaCl, – H2O – NaCl
Salicylaldehyde
8. (a) CH3
CH3 – CH – OH Dehydration/(H+) CH3 – CH = CH2
Isopropyl alcohol
(b) CH3 CH2

CH3 – C – OH Dehydration/(H+) CH3 – C – CH2
CH3
Tertiary butyl alcohol
(c) CH3 CH2 CH2 CH2 OH Dehydration/(H+) CH3 – CH2 – CH = CH2

n-Butyl alcohol
(d) CH3 CH3 CH2

CH3 – C – CH2 – OH Dehydration/(H+) CH3 – C = CHCH3 + CH3 – C – CH2CH3
CH3 (Major) (Minor)
Neopentyl alcohol
(e) OH
CH3 – CH2 – CH – CH2 – CH3 Dehydration/(H+) CH3 – CH = CH – CH2 – CH3
3-Pentanol Pent-2-ene
9. (b) The mechanism of dehydration of alcohol involves the following steps:

1. Formation of protonated alcohol
2. Formation of carbocation
3. Formation of ethane by elimination of a proton
10. (c) PCC is the mixture of pyridine, CrO3 & HCl. With the help of PCC, alcohols are oxidised to aldehydes.
CH3CH2CH2 – CH – CH2OH PCC/[O] CH3CH2CH2 – CH – CHO
CH3 CH3
2-Methylpentan-1-ol 2-Methylpentan-1-ol

11. (c) CH3 – CH = CH2 BH3 , THF / Hydroboration (CH3CH2CH2)3B H2O2 / OH– 3CH3CH2CH2OH
Tripropyl borane 1-Propanol
12. (a) OH OOCC 6H5 OOCC6H5

C6H5COCl/base Conc. HNO3 + H2SO4
Benzoylation (–HCl) Nitration
Phenol Phenyl benzoate 4-Nitrophenyl benzoate

(X) (Y)
13. (b) CH3 CH3
CH C – O – OH
OH CH3 CH3
Zn/Δ AlCl3 / CH3CH2CH2Cl O2
Phenol Benzene Isopropyl benzene

(B) (C)
14. (a) OH 𝑂− 𝑁𝑎 + OH OH
COONa COOH
NaOH CO2 dil. HCl
1250C , 6 atm
Salicylic acid
15. (d) OH OH
O2N NO2
Conc. HNO3
(Excess)
Phenol (Picric acid)
NO2
2,4,6-Trinitrophenol
(Picric acid)
1
16. (b, c) 𝐵𝑜𝑖𝑙𝑖𝑛𝑔 𝑝𝑜𝑖𝑛𝑡 ∝ 𝐵𝑟𝑎𝑛𝑐ℎ𝑖𝑛𝑔
𝑆𝑜𝑙𝑢𝑏𝑖𝑙𝑖𝑡𝑦 ∝ 𝐵𝑟𝑎𝑛𝑐ℎ𝑖𝑛𝑔
17. (b) Lucas test distinguish 10 , 20 & 30 ALCOHOLS.
Primary alcohol – no colour
Secondary alcohol – cloudiness in 5 minutes
Tertiary alcohol – cloudiness appears immediately.
18. (d) Dehydration of alcohols can be carried out either with protonic acids such as conc. H2SO4 , H3PO4 or
catalysts such as anhydrous zinc chloride or alumina.
19. (d) In the given conversion, Markownikof’s addition of water is required. However, the carbocation
formed in this case undergoes rearrangement to give 2-methylbutan-2-ol. Therefore, the best
method in this case is oxymercuration-demercuration reaction.
CH3 (i) Mercuric acetate + H2O / THF CH3 OH
CH3 – CH – CH = CH2 (ii) NaBH4 / OH-- CH3 – CH – CH – CH3
3-Methylbut-1-ene 3-Methylbutan-2-ol
20. (d) Nitro group has both –R effect & –I effect. A nitro group at o- & p-position withdraws electrons of
O – H bond by the stronger –R effect while the – NO2 group at m-position withdraws electrons of
the O – H bond by the weak – I effect. Thus, o- & p-nitrophenols are more acidic than m-nitrophenol.
But if we compare the acidity of o-nitrophenol & p-nitrophenol, then o-nitrophenol is less acidic than
p-nitrophenol due to intramolecular H-bonding which make loss of proton little more difficult.

21. (b) Phenol is most acidic of all the given compounds. In phenol, the electron withdrawing phenyl ring
polarizes the O – H bond thereby facilitating the release of H as H+ & hence phenol is most acidic.
In J – CH2OH the electron withdrawing effect of phenyl ring is somewhat diminished by
–CH2 group & it is therefore less acidic than phenol. In (c) & (d), –OH group is attached to alkyl
groups which due to their +I effect reduce the polarity of –OH bond & so, the acidity strength is low.
22. (a) Phenols on reaction with chloroform in presence of aqueous sodium or potassium hydroxide solution
followed by acidification yields 2-hydroxybenzaldehyde i.e., salicylaldehyde.
23. (c) Aspirine, an antipyretic i.e., acetylsalicylic acid, i.e., a drug which is responsible for lowering the
temperature of body to normal. Another common antipyretic is paracetamol.
OCOCH3
COOH
Acetylsalicylic acid (Aspirine)
24. (a) Degree of unsaturation of C10H18O = 2, but it contains no double or triple bond. Hence, there are two
rings – one six membered as indicated by product & the other three membered which is cleaved by
HCl due to strain. Hence A has following structure:
OH
H3C – C – CH3
25. (a) H3C CH3 O – OH

CH H 3C – C – CH3 OH
O2/Catalyst H2O/H+ + (CH3)2CO

Acetone
Cumene Phenol
26. (a)
27. (a) Catechol is most acidic out of all dihydric phenols.
OH 𝑂̅𝑁𝑎 + O
NaOH CH2I2/-2NaI
OH 𝑂̅𝑁𝑎 + O
28. (c)
29. (c) It is a Friedel-Crafts reaction.
OCH3 OCH3
CH3COCl/Anhy. AlCl3
Anisole COCH3
4-Methoxyacetophenone
30. (b) O I
HI (excess)/Δ + HCHO
O CH2 – I
Ethers are readily cleaved by action of HI to form alcohol & alkyl halide.
R – O – R + HX → RX + R – OH
If excess of halogen acid is used, then alcohol formed reacts further with halogen acid to produce
alkyl halide.

31. (b) Williamson’s synthesis (SN2) given by 10 alkyl halides.

32. (a) Williamson’s synthesis occurs by SN2 mechanism & primary alkyl halides are most reactive in
SN2 reactions.
33. (a) Diphenyl ethers are not cleaved by HBr or HI.
34. (d) The formation of methyl t-butyl ether by the reaction of sodium tertiary butoxide & methyl bromide
involves nucleophilic substitution (SN2) reaction of alkyl halides in which halogen is replaced by
alkoxy group.
35. (d) If A reacts with HI, it could be ether
CH3 – O – C2H5 HI (Excess) CH3I + C2H5I + H2O
(A) (X) (Y)
C2H5I Aq. KOH C2H5OH

(Y) (Z)
36. (a) Due to the presence of loan pair of electrons on oxygen atom, ethers behaves as bases & form stable
oxonium salts with minerals acids.
C2H5 – O – C2H5 + HCl ̅
C2H5 – O+ – C2H5Cl
H
Diethyl oxonium chloride
37. (a) OCH3 OCH3 OCH3 OH

Cl Cl
(CH3)3CCl Cl2 HBr
AlCl3 FeCl3 Δ
C(CH3)3 C(CH3)3 C(CH3)3

Anisole is decomposed by HBr or conc. Hydroiodic acid to give phenol.
This reaction is used for estimation of methoxy group (Zeisel’s Method).
38. (c) Boiling points of alcohols are much higher due to formation of hydrogen bond between the hydroxyl
groups of molecules of alcohol with the result several molecules are associated to form an extensive
intermolecular H-bonding which is not possible in case of ether molecules due to lack of hydroxyl
groups.
H–O–––H–O–––H–O
R R R
39. (c) 5R – O – R + P2S5 5R – S – R + P2O5
Thioether
40. (a)
41. (b) A mixture of 20% ethanol & 80% gasoline (petrol) called power alcohol is used in internal combustion
engines to drive power.
42. (b) The dehydration of alcohol is an example of elimination reaction. the alcohols on dehydration yield
alkenes or olefins.
The order of ease of dehydration is tertiary alcohols > secondary alcohols > primary alcohols.
The process of dehydration is done either by heating the alcohol with concentrated sulphuric acid
or phosphoric acid at higher temperature.
CH3CH2OH Al2O3 / 3500C CH2 = CH2 + H2O
43. (c) Lucas test is employed to distinguish between 10 , 20 & 30 alcohols.
Lucas reagent, i.e., conc. HCl & anhyd. ZnCl2 , is added to alcohols & the appearance of turbidity due
to the formation of alkyl chloride helps in the distinction of alcohols.
If turbidity appears immediately, alcohol is tertiary.

If turbidity appears in 5 minutes, then alcohol is secondary.

If solution remains clear, i.e., no turbidity, alcohol is primary.
44. (b) CH3CH2OH [O] CH3COOH
46g 60g
45. (d)
46. (a) OH Br
PBr3 alc. KOH
47. (a) OH OH OH
NO2
Dil. HNO3 +
298K
o-Nitrophenol NO2
(40% Major) P-Nitrophenol
(13% minor)
48. (a) Weaker acids have higher pKa – OCH3 at meta-position exerts only –I effect,
hence increases the acidity.
– I effect order : –NO2 > –OCH3 > –Cl
– CH3 has +I effect.
So, the order is (a).
49. (a) Ammonia upon reaction with phenol in the presence of anhydrous ZnCl 2 forms aniline.
50. (a)
– O – CH3 HI – OH + CH3I

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Chapter – 2

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Formula Of Alcohol Common Name IUPAC Name

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Solution: (a) Alcohols (i), (ii) & (iii) are primary.

Cyclobutanol Cyclopropyl methanol 1-Methylcyclopropanol

(d) CH3 OH (e) H OH

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6 METHODS OF PREPARATION OF ALCOHOLS

Oxymercuration Demercuration Hg(OAc)2

By Grignard Reagent CH3MgBr H2O/H+

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Illustration: 1. Write structures of the products of the following reactions:

(iii) CH3 – CH2 – CH – CHO NaBH4

(iii) CH3 – CH2 – CH – CH2OH

Solution:(i) CH3 – CH2 – CH2 – CH2 – OH

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Illustration: 4. Write the products name of the following reactions:

(v) R – CH = CH2 + Hg(OCOCH3)2 H2O (A) NaBH4 (B) + (C) + (D)

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 Chemical Properties & Reactions of Alcohol:

Reactions involving the H-atom of (– OH) group:

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Reactions involving (– OH) group:

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Reactions involving both alkyl & (– OH) group:

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 Distinction between 10 , 20 and 30 alcohols

O [O] Na2Cr2O7 [O] Na2Cr2O7

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Interconversions Among Different Classes Of Alcohols

CH3CH2CH(OH)CH3 HI CH3CH2CHICH3 (CH3)3N CH3CH2CHCH3 AgOH/Δ CH3CH2CH=CH2

V. Secondary (20) alcohol to tertiary (30) alcohol:

VI. Higher alcohol to lower alcohol (step down):

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Further they can be substituted phenols. Examples are:

2-Hydroxybenzaldehyde 2-Hydroxyacetophenone 2-Hydroxybenzoic acid

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3 METHODS OF PREPARATION OF PHENOLS

From Aryl Sulphonic

Benzene Sod. Benzene Sod. Phenoxide Phenol

From Aryl Halides

Chlorobenzene Sod. Phenoxide Phenol

Sodium salicylate Sod. Phenoxide Phenol

From Aryl Halides

Phenyl Phenoxy Phenol

4 COMMERTIAL METHOD OF PREPARATON OF PHENOLS

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Illustration: 1. Complete the following reaction :

Conc H2SO4 /Δ (A) NaOH /Δ (B) H2SO4 (C)

Conc H2SO4 /Δ NaOH /Δ H2SO4

Benzene Benzene sulphonic Sodium phenoxide Phenol

Chlorobenzene Sodium phenoxide Phenol