Class-XII

Alcohols Phenols Ethers

Monohydric alcohols

Containing one OH group

C2H5OH Ethanol OH H2C

OH Phenol CH 2

Dihydric alcohols

Containing two OH groups

Catechol OH

OH OH Ethyleneglycol
HO OH

Trihydric alcohols

Containing three OH groups OH group 2o

OH H3C HC CH3 OH

H2 C OH

CH OH Glycerol

CH 2 OH
OH

Monohydric alcohols having C Types Alkyl alcohols Allylic alcohols

H3C

Benzene- 1, 2 , 4- triol

SP3

1o
CH 2

3o
CH3 H3C C CH3 OH

H2C

CH

CH 2

OH H2C

CH

CH CH3

OH H2C CH

CH3 C CH3 OH

Benzylic alcohols

CH 2

OH

CH CH3

OH

CH3 C CH3 OH

Monohydric alcohols having C

SP2

OH group
H2C CH OH

OH

OH

Preparation of alcohols
[1] From alkene ( acid catalysed hydration )
H2C CH CH3

CH3

H2O

OH H3C CH CH 3

[2] From alkene ( Hydroboration )

H3C CH H3BO 3 CH2

(BH 3)2

H3C

CH 2

CH 2 OH

BH 2

H2C

CH

CH3

( CH 3CH 2CH 2 ) 2BH CH CH3

3 CH 3CH 2CH 2 OH ( Highly pure ) CH2

H2O 2

( CH 3CH 2CH 2 ) 3B H2C

OR

H3C

CH

B 2H6

H2O 2

OH

3 CH 3CH 2CH 2 OH

H3BO 3

[3] From Aldehyde and Ketone ( Reduction by H2 / Pt

O R C H Aldehyde O R C R Ketone H2 / Pt R NaBH 4 R CH 2 OH

or

H2/Ni

or

H2/Pd

or

NaBH4 )
O

H2 / Ni

Primary alcohol

R C H Aldehyde O

OH CH R H2 / Pd R

C Ketone

Secondary alcohol

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Page - 1

Class-XII

Alcohols Phenols Ethers

Monohydric alcohols

Containing one OH group

C2H5OH Ethanol OH H2C

OH Phenol CH 2

Dihydric alcohols

Containing two OH groups

Catechol OH

OH OH Ethyleneglycol
HO OH

Trihydric alcohols

Containing three OH groups OH group 2o

OH H3C HC CH3 OH

H2 C OH

CH OH Glycerol

CH 2 OH
OH

Monohydric alcohols having C Types Alkyl alcohols Allylic alcohols

H3C

Benzene- 1, 2 , 4- triol

SP3

1o
CH 2

3o
CH3 H3C C CH3 OH

H2C

CH

CH 2

OH H2C

CH

CH CH3

OH H2C CH

CH3 C CH3 OH

Benzylic alcohols

CH 2

OH

CH CH3

OH

CH3 C CH3 OH

Monohydric alcohols having C

SP2

OH group
H2C CH OH

OH

OH

Preparation of alcohols
[1] From alkene ( acid catalysed hydration )
H2C CH CH3

CH3

H2O

OH H3C CH CH 3

[2] From alkene ( Hydroboration )

H3C CH H3BO 3 CH2

(BH 3)2

H3C

CH 2

CH 2 OH

BH 2

H2C

CH

CH3

( CH 3CH 2CH 2 ) 2BH CH CH3

3 CH 3CH 2CH 2 OH ( Highly pure ) CH2

H2O 2

( CH 3CH 2CH 2 ) 3B H2C

OR

H3C

CH

B 2H6

H2O 2

OH

3 CH 3CH 2CH 2 OH

H3BO 3

[3] From Aldehyde and Ketone ( Reduction by H2 / Pt

O R C H Aldehyde O R C R Ketone H2 / Pt R NaBH 4 R CH 2 OH

or

H2/Ni

or

H2/Pd

or

NaBH4 )
O

H2 / Ni

Primary alcohol

R C H Aldehyde O

OH CH R H2 / Pd R

C Ketone

Secondary alcohol

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Class-XII

Alcohols Phenols Ethers

[4] From Aldehyde and Ketone ( By using Grignard Reagent ) + O O Mg Br +

R Mg Br

H2O

HO
R C OH

C R

Mg Br

Carbonyl compound

Alcohol +
H

Formaldehyde will give primary alcohol +

O

O Mg Br H H C CH3 H

H2O

HO
OH

CH 3 Mg Br

H3C

C H

Mg Br

Formaldehyde

Primary alcohol
CH3 H3C C H OH

Aldehydes ( except formaldehyde ) will give secondary alcohol. O + + O Mg Br H O

CH 3 Mg Br

CH3

HO

C CH3 O Mg Br

Acetaldehyde

CH3

Mg Br

Secondary alcohol
CH3

Ketones will give tertiary alcohol.

CH 3 Mg Br

H3C

CH3

H3C

C CH3

CH3

H2O

HO
OH

H3C

C CH3

Mg Br

Ketones

Tertiary alcohol
R CH 2 OH

[5] From Carboxylic acid O

R C OH Carboxylic acid ( 1 ) LiAlH 4 ( 2 ) H 2O H2 OR Catalyst

Primary alcohol

[6] From Esters

R

O C Esters

CH 2

OH

OH

Primary alcohol

alcohol.

LiAlH 4 is an expensive reagent, so acid should convert into ester before cnversion into

Properties of alcohols
H H

[1] When alcohols act as nucleophile, the O H bond breaks.

..
O

[2] Protonated alcohols act as electrophile, the C O bond breaks. + .. + H Nu R CH 2 OH R CH 2 OH 2 R CH

[3] Acidic nature

R

The acidic character of alcohol is due to polarity of OH bond. Electron releasing groups decrease the polarity of OH bond , so acid strength of alcohol is:
H R C H OH R R C H OH R R C R OH

Jayanta kumar sahu PGT : Chemistry Kendriya Vidyalaya Sangathan

..
..
1
o

Nu

H2O

.. O ..

Acid

Base

R O Conjugate base

BH Conjugate acid

..
2o

3o

Page - 3

Class-XII
2 ROH 6 (CH 3)3C OH tert.butylalcohol

Alcohols Phenols Ethers

+ +

2 Na Al

2 RONa

+ +

H2 3 H2

[ (CH 3)3 C O] 3 Al Aluminiumtert.butoxide

+

[4] Esterification
RCOOH Acid O R C O O C R

+ +

HOR' Alcohol

RCOOR' Ester H
+

+ +

H2O

Acid anhydride O H3C C Acid chloride Cl

HOR' Alcohol

RCOOR' Ester

RCOOH Acid

Pyridine HOR' Alcohol

RCOOR' Ester

[ Pyridine neutralises the HCl produced in the reaction]

[5] Reaction with Lucas reagent ( concn HCl & ZnCl2 )

ROH Alcohol

HCl

ZnCl 2

RCl

H 2O

Soluble w ith each other

Insoluble w ith each other

[6] Reaction with PCl3

3 ROH

PCl 3

3 RCl

H3PO 3

[7] Dehydration Protic acid i.e concn. H2SO4, H3PO4 or catalyst such as Al2O3 or ZnCl2 used as dehydrating agents. H OH

eh rd Fo

H2C CH 2 Primary alcohol ( Ethanol ) OH H

Conc. H 2SO 4 443 K

H2C CH2 Alkene ( Ethene )

+ +

H2O

ra yd tio

H3C CH CH 2 Secondary alcohol ( Propan - 2-ol ) OH H3C C H CH 2

85% H 3PO 4 440 K

H3C

CH Propene

CH 2

H2O

> 2
o

> 1

20% H 3PO 4 358 K

H3C

C CH3

CH 2

H2O

al l ho co

CH3 Tertiaryalcohol ( 2 - Methylpropan - 2 - ol )

2 - Methylpropene

a Oxid

[8] Oxidation

Oxidising power of HNO3 or KMnO4 > CrO3

Anhydrous CrO 3 Anhydrous CrO 3

tion

Aldehyde / Ketone
RCHO Adehyde O R C Ketone CH3

Alcohol
RCH 2OH Primary OH

KMnO 4 / H KMnO 4 / H
+

Acid
RCOOH

o > 3 o > 2 of 1

Anhydrous CrO 3

CH Secondary OH C

CH3

KMnO 4 / H

RCOOH

+ +

H2O

CO 2

hol alco

No reaction

Anhydrous CrO 3

CH3

KMnO 4 / H

RCOOH

H2O

CO 2

CH3 Tertiary

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Class-XII

Alcohols Phenols Ethers

RCH 2OH Primary Cu / 573 K Dehydrogenation Cu / 573 K Dehydrogenation Cu / 573 K Dehydration R C CH3 CH2 ( Alkene ) R RCHO O C CH3 ( Ketone ) ( Aldehyde )

[9] Dehydrogenation
OH R OH R C

CH CH3 Secondary CH3

CH3 Tertiary

Pr epar at ion
[1] From haloarenes

PHENOL ( Carbolic Acid )

Cl

-+

O Na H
+

+
Chlorobenzene

NaOH

623 K 300 atm. Sodiumphenoxide

OH

Phenol OH

[2] From Benzenesulphonic acid

SO 3H NaOH H
+

Phenol
ONa

SO 3 + H 2SO 4

SO 3 H

NaOH - H2O

SO 3 Na

Fused NaOH - NaHSO 3

OH

[3] From Benzenediazonium chloride

N2 Cl Warm H 2O

OH

+
OH

N2

+
O

HCl

[4] From Cumene ( Isopropyl benzene )

CH3 HC CH3 CH3 O2 CH3 C O O H Dilute Acid

H3C

Acetone

CH3

Pr oper t ies
[1] Acidic nature
OH

+ +

Na

ONa

+ +

H2

Sodium phenoxide OH NaOH ONa H2O

[2] Esterification The introduction of acetyl group in alcohols or phenols is known as acetylation. Acetylation of salicylic acid produces aspirin.
COOH

+
OH Salicylic acid

( CH 3CO ) 2 O

COOH

+
OCOCH
3

CH 3COOH

Acetylsalicylic acid ( Aspirin )

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Class-XII
[a] Nitration
OH O 2N

Alcohols Phenols Ethers

OH OH NO 2 Conc. HNO
3

[3] The electrophillic sustitution

OH NO 2 Dilute HNO
3

+
Ortho nitrophenol
OH NO 2

NO 2

2,4,6-Trinitrophenol ( Picric acid )

Phenol

Para
OH

[b] Halogenation
OH Br Br Br 2 Water ( Solvent of high polarity ) Br OH Br 2 CS 2 ( Solvent of low polarity ) ( Minor ) Phenol Br

+
Br ( Major )

2,4,6-tribromophenol [4] Reaction with Zinc dust

OH

Zn

+
O O

ZnO

[5] Oxidation
OH

Na 2Cr 2O 7 H2SO 4

Benzoquinone

Name reactions
Kolbe's Reaction
OH NaOH O Na CO 2 H
+

OH COOH 2-Hydroxybenzoic acid

( Salicylic acid )
OH CHO H
+

Reimer-Tiemann Reaction
OH CHCl
3

O Na CHCl
2

O Na NaOH

CHO

aq. NaOH

2-Hydroxybenzaldehyde

( Salicylaldehyde)

Role of PCC
Pyridiniumchlorochromate ( C5H5NH )+ ClCrO3

N Cl Cr O -3
+

PCC oxidises CH2 OH group upto aldehyde without affecting other groups.
H3C CH CH CH 2 OH

PCC

H3C

CH

CH

CHO

Role of sodiumborohydride ( NaBH 4 ) and Lithiumaluminiumhydride ( LiAlH 4 )

Both will reduce carbonyl group into alcohol group, but NaBH4 can reduce carbonyl group without affecting C= C in conjugation with carbonyl group.
O H3C CH 2 CH 2 CH 2 OH

LiAlH4

H3C

CH

CH

NaBH4

H3C

CH

CH

CH 2 OH

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Page - 6

Class-XII
C O
xx
xx

Alcohols Phenols Ethers

Explanations
H

bond angle in alcohol is less than normal tetrahedral angle. Because Lp-Lp repulsion is greater than Lp-Bp repulsion

C
xx

bond angle in phenol is slightly more than alcohol, because the lone pair electron H density on oxygen of phenol is slightly decreases due to resonance. So Lp-Lp xx repulsion of phenol is less than alcohol.
C

C O
xx
xx

bond angle in ether is slightly greater than normal tetrahedral angle due to repulsive interaction between the two bulky alkyl groups.

O bond length in phenol is slightly less than C O bond length of ethanol. This is due to partial double bond character of C O bond of phenol due to resonance C O is polar towards oxygen. The dipolemoment of phenol is smaller than methanol, because the electrons on oxygen of phenol get delocalised towards benzene ring, but in case of methanol, due to electron donating effect of -CH3 group, C O bond becomes more polar. C

The high boiling point of alcohol and phenol is due to presence of intermolecular hydrogen bonding ,which is not possible incase of hydrocarbons and ethers.
R O R H O O H H

Ether is soluble in water by forming hydrogen bonds

H

ether

water

The boiling point of alcohols decrease with increase of branching in carbon chain, because the van der waals forces decrease with decrease in surface area. The solubility of alcohols and phenols in water is due to their ability to form hydrogen bonds with water molecules. The solubility decreases with increase in size of alkyl or arene (hydrophobic ) groups i.e.the solubility of methyl alcohol is greater than ethyl alcohol in water. Alcohol is less acidic than water because conjugate base of alcohol is less stable than that of water. +
R OH R O

Alcohol
H2O

Alkoxide ion ( less stable, due to high electron density on oxygen atom )
H O

Hydroxide ion, more stable as compared to RO

Phenols are stronger acid than alcohol and water, because of conjugate base of phenol i.e. phenoxide ion is more stable due to resonance.
OH

+
O

PKa = - log Ka = log 1/ Ka i.e. P

Ka

1/Ka

Acid strength Ka 1/ PKa

i.e. greater the PKa value weaker will be the acid. Ethanol mixed with methanol is called denatured alcohol. Inside the human body methanol is oxidised to methanal and then to methanoic acid which may cause blindness or death. Methanol poisoned patient is treated by giving intravenous injection of dilute ethanol. Orthonitrophenol is steam volatile due to intramolecular hydrogen bonding ,paranitrophenol is less volatile due to intermolecular hydrogen bonding , which causes assocation of molecules.
O H O N
+

H O
O
-

O N
+ -

H O N
+

O
-

O-nitrophenol

P-nitrophenol

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Class-XII

Alcohols Phenols Ethers

For the formation of alkene :
CH 2 CH 2

Explain why dehydration of alcohol to form alkene is always carried out with conc. sulphuric acid and not with conc. HCl or conc.HNO3 .
R CH 2 CH 2 OH H
+

OH 2

+ H2O
R CH 2 CH 2

( Carbocation )

If HCl is used Cl ( Nucleophile) give substitution product. If H2SO4 is used ( non nucleophile ) give ellimination product.
H R CH

CH 2

HSO 4

CH

CH 2 CH 2 Cl

[ Ellimination reaction ] [ Substitution reaction ]

Cl

CH 2

If HNO3 ( Oxidising agent ) is used, alcohol will oxidise to aldehyde or ketone and next oxidise to acid. Explain bromination of benzene takes place in presence of FeBr3 but bromination of phenol require no FeBr3. Bromination of benzene takes place in presence of lewis acid ( FeBr3 ) which polarises Br - Br molecule. Incase of phenol the polarisation of bromine molecule occur in absence of lewis acid, because highly activating effect of OH group attached to benzene ring make the bromine molecule polar. Br

+
OH

Br 2

FeBr 3 OH Br

Br 2

Br

OH

Explain phenol becomes dark when exposed to air. In presence of air phenols are slowly oxidised to a dark coloured mixture containing quinones.
OH O2

O
( Benzoquinone )

Test for primary, secondary and tertiary alcohols This can be done by Lucas test ( Lucas reagent - conc.HCl & ZnCl2 ) * Tertiary alcohol produce cloudiness within one minute. * Secondary alcohol produce cloudiness within five minutes. * Primary alcohol do not produce cloudiness at room temperature OH due to less polarity.
R R C R R R CH OH ZnCl 2 Room temperature ZnCl 2 Room temperature OH R

+ + +

HCl

ZnCl 2 Room temperature

C R R

Cl

HCl

CH Cl

CH 2 OH

HCl

No reaction

Test for alcohol containing H3C group. CH This test is performed by iodoform test. These alcohols give yellow precipitate of iodoform when treated with alkaline solution of iodine.
CH 3CH 2OH

4 I2

6 NaOH

CHI 3

HCOONa

5 NaI

5 H 2O

Yellow precipitate

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Class-XII

Alcohols Phenols Ethers

Test for phenol

Litmus test Ferric chloride test Azo dye test Bromine water test Phenol turns blue litmus red. Phenol react with neutral ferric chloride solution to give violet colouration.

Phenol react with diazonium salt in weakly basic medium to form yellow or orange coloured due. With bromine water phenol give a white precipitate of 2,4,6-tribromophenol.

METHANOL (Wood Sprit )

Wood
Destructive distillation

Methanol

Catalytic hydrogenation of carbon monoxide give methanol

CO

2 H2

ZnO - Cr 2O3 200 - 300 atm. , 573 - 673 K

CH 3OH

Methanol is used as a solvent in paints and varnishes and for making formaldehyde.

ETHANOL
It is prepared by fermentation of sugar which takes place in absence of air (anaerobic condition )with production of carbon dioxide gas. As grapes ripen , the quantity of sugar increases and yeast grows on the outer skin. When grapes are crushed, sugar and enzyme comes in contact and fermentation starts.
C12H22O11 Sugar

+
C6H12O6

H2O

Invertase

C6H12O6 Glucose & Fructose 2 C 2H5OH

Zymase

CO 2

The action of enzyme inhibits if alcohol formed exceeds 14% If air gets into fermentation mixture, the oxygen of air oxidises ethanol to ethanoic acid and it destroys the test of alcoholic drink.

ETHER
R = R1 simple ether
R O R1

R= / R1

mixed ether

Preparation
[1] Dehydration of Alcohol
2 C 2H5OH H2SO 4 413 K H5C2 O C2H5

Ethoxyethane

It is not possible to prepare mixed ether, because when we take different alcohols, as starting material, we will get a mixture of ethers, which is difficult to to separate. Alcohols give ether by SN2 mechanism at low temperature, So for the formation of ether , the reactivity of alcohol is 1o > 2o > 3o Alcohols give alkene by ellimination reaction at high temperature, So for the formation of alkene, the reactivity of alcohol is 3o > 2o > 1o [2] Williamson synthesis
R O Na

This is used to prepare both simple and mixed ether

R1 X R O R1

-+

NaX

The reaction involves SN2 attack of an alkoxide ion on primary alkyl halide. If alkyl halide used is tertiary then alkene will be the main product.

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Class-XII
CH3 H3C C CH3

Alcohols Phenols Ethers

CH3 O Na

- +

+
H

H3C

Br

H3C

C CH3

CH 3 Ether

CH3 CH 2 C CH3 Br H2C

CH3 C CH3 Alkene

H3C

O Na

- +

+
NaOH

OH

- +

H3C

Br O CH 3 Anisole

O Na

Reaction of ether with HX

R O R1

Reactivity of
R X

HI > HBr > HCl

+
xx xx

HX

R1 OH R1 OH

Case-1
O CH 3

HX

R1 X CH 3Br

+ H2O

HBr

OH

stronger due to partial double bond character Case-2

H3C O CH 2 CH3

HI

CH 3I

+
CH3

CH 3CH 2OH

Since by SN2 mechanism I ( nucleophile ) attack to the smaller alkyl group ( CH3 ) Case-3
H3C CH3 C CH3 O CH3

HI

H3C

C CH3

H3C

OH

By SN1 mechanism C O bond of t-butyl group break to produce stable ( CH3 )3C+

Electrophilic substitution
Br2 in ethanoic acid

OCH 3 Br

+
OCH 3 O C CH3 O

Br

OCH 3

OCH 3

CH 3COCl AlCl 3 OCH 3 CH 3Cl AlCl 3 OCH 3 H2SO 4 HNO 3

+
H3C

OCH 3

CH3

H3C

OCH 3

NO 2

O 2N

OCH 3

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Class-XII

Alcohols Phenols Ethers

H
xx

Mechanism of reaction of HI with ether

[1] Protonation of ether
H3C O
xx

CH 2

CH3

[2] I acts as nucleophile and attack the least substituted carbon of the oxonium ion by SN 2 mechanism H I

HI

H3C

CH 2

CH3

H3C

CH 2

CH3

H3C

+
+

H3C

CH 2

OH

[3] If excess of HI is there and temperature is very high:

H3C CH 2
xx

OH xx

H CH 2

I OH 2

H3C H3C

CH 2 CH 2

OH 2 I

+ +

I
H2O

H3C

If there is tertiary alkyl group, then the reaction will proceed by SN 1 mechanism.
CH3 H3C C CH3 CH3 H3C C O
+
xx

CH3 O
xx

CH3

H3C

CH3

CH3 H CH3 CH3

slow

H3C CH3

H3C

OH CH3 H3C
OH CO2 H
+

CH3 H C+ CH3

CH3

H3C

+
OH

fast
+

C CH3

Mechanism of Kolbe's reaction

+

O Na NaOH

COOH

2-Hydroxybenzoic acid

( Salicylic acid )
OH H
+

OH NaOH

O Na

O C O

OH H O C

+
COONa

O Na

COOH

Mechanism of Reimer-Tiemann reaction

OH CHCl 3 aq. NaOH O Na CHCl 2 NaOH

O Na CHO H
+

OH CHO

2-Hydroxybenzaldehyde

( Salicylaldehyde)

Step-1

Generation of electrophile ( 1,1-elimination ) Cl xx OH Cl C Cl Cl C H Cl Cl Reaction of electrophile with phenoxide

O
xx

xx

Cl

C Cl

Cl

Step-2
O

Dichlorocarbene ( Electrophile )
O

Cl

Step-3

Hydrolysis O
CHCl 2

C Cl
O

CHCl 2
2

Cl

o-dichloromethylphenoxide

HC

OH

OH CHO

OH H2O

OH

H2O

CHO

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Class-XII
O C

Alcohols Phenols Ethers

Mechanism of LiAlH4 &

LiAlH 4 R
+

NaBH4
R

OH CH R

R LiAlH 4

or Li

NaBH

+
O R C

AlH 4
R
R

AlH 3 H

OAlH 3 R R CH R

OAlH 3 R CH R

CH R

Al 4
+

OH 3 H 2O

3 R
O

CH

Al(OH) 3

Mechanism of Esterification
O R C

Bond cleavage
OH

Carboxylic acid

H H O R1

Alcohol
O H R C OH
O R C O H
x x xx

Ester
+

OR 1

[1] Protonation of carboxylic acid

O R
H OH
+

H OH

[2] Attack of alcohol on carbonyl carbon ( addition ) O R C

+

H OH

xO xx x

R1

R1 O
+

[3] Elimination of leaving group

O R H C O
+

H OH R1 O C O R1
+

O C O

H O H H R1
+

C O R1

[4] Deprotonation
R

O R C OR 1

Mechanism of hydration of alkene

R CH CH2

H2O
+

HO R CH CH3

[1] Protonation of alkene H2O

+
CH

H3O H
+ +

CH2

CH CH3 Carbocation O
+

[2] Nucleophilic attack of water on carbocation H

+

H CH3

CH

CH3

xx

H2O

xx

CH

[3] Deprotonation to form an alcohol H R O

+

H H
xx

O CH CH3

CH

CH3

H2O

xx

H3O

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Class-XII

Alcohols Phenols Ethers

Conc. H 2SO 4 443 K

Mechanism of dehydration of alcohol for the formation of Alkene

R CH 2 Alcohol CH 2 OH R CH Alkene H CH 2
xx

CH 2

[1] Protonation of alcohol R CH 2 O

xx

Fast

R
+

CH 2

CH 2

[2] Formation of carbocation R CH 2 CH 2

H O
+

Slow H H

CH 2

CH 2 Carbocation

[3] Deprotonation to form an alkene R

HC

CH 2

CH

CH 2

Mechanism of dehydration of alcohol for the formation of Ether

R CH 2 OH Conc. H 2SO 4 413 K
xx

CH 2 O

CH 2

R H

[1] Protonation of alcohol R

CH 2

xx

+
CH 2

H H

Fast

CH 2 H

[2] Attack of alcohol on oxonium carbon ( addition ) R CH 2

xx

O H Oxonium ion

xx

Slow H

SN
+

CH 2

CH 2

[3] Deprotonation to form an ether H R CH 2 O

+

H
CH 2 R HO

CH 2

CH 2

Predict the products

H3C O CH CH2

+
O

H2O NaBH 4

? ? ?

H3C

CH

CH3

OH CH 2 C O O CH3

CH 2

C O

CH3

H3C

CH 2

CH CH3

CHO

NaBH 4

H3C

CH 2

CH CH3

CH 2

OH

H3C

CH 2 O

CH 2

CH3

+
HBr

HBr

? ?

H3C

CH 2

CH 2

OH

H3C

Br

C2H5

OH

+
O C2H5

+
OC 2H5

H5C2

Br

Conc. H 2SO 4 Conc. HNO

3

? ?

OC 2H5

+
NO 2 O 2N

( CH 3 ) 3C

C2H5

HI

( CH 3 ) 3C

C2H5OH

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