AYESHA FIAZ BSBCH-001

ORGANIC
CHEMISTRY
PREPERARTION &
REACTION
MECHANISM OF
ALCOHOLS
o What is alcohol?
Alcohol, any of a class of organic
compounds characterized by one or
more hydroxyl (―OH) groups
 attached to a carbon atom of an alkyl
group (hydrocarbon chain).
Example:CH3-CH2-OH
 Properties of alcohol:
Chemical Properties of Alcohols
Alcohols exhibit a wide range of
spontaneous chemical reactions due to the
cleavage of the C-O bond and O-H bond.
Some prominent chemical reactions of
alcohols are:
Oxidation of Alcohol

 Alcohols undergo oxidation in the

presence of an oxidizing agent to
produce aldehydes and ketones which
upon further oxidation give carboxylic
acids.
Dehydration of Alcohol
 Upon treatment with protic acids, alcohols
undergo dehydration (removal of a molecule
of water) to form alkenes. Dehydration of
alcohol
Physical properties of
alcohols:
Colour and odour:
Lower alcohols are generally colourless
toxic liquids with characteristics sweet smell
and burning taste.

Solubility:
They are readily soluble in water but
solubility decreases in higher alcohols.The
solubility of alcohols is due to hydrogen
bonding which is prominent in lower
alcohols but diminishes in higher alcohols.
Melting and boiling
points
Melting and boiling points of alcohols are
higher than corresponding alkanes.Methyl
alcohol and ethyl alcohol are liquids while
methane and ethane are gases. This is also
due hydrogen bonding which is present in
alcohols and absent in alkanes.
  PREPARATION OF
ALCOHOL
From Alkenes:
By acid catalysed hydration
of alkenes
Alkenes react with water in the presence
of acid as catalyst to form alcohols.
In case of unsymmetrical alkenes, OH is
added to the carbon having less number of
hydrogen atoms (Markownikov’s rule).

Mechanism of Hydration of
Alkenes
The following steps are involved in the
reaction:
Step 1: Alkene undergoes protonation to
form carbocation by electrophilic attack of
H3O+.
Step 2: Water, being a nucleophile, attacks
on the carbocation.

Step 3: Deprotonation occurs to form an

alcohol.

Oxymercuration/
Demercuration
The reaction of alkenes with mercuric
acetate [(CH3COO)2Hg] followed by
reduction gives alcohol according to
markovnikov's rule.
.

Hydroboration-oxidation
reaction
Hydroboration–oxidation
reaction is a two-
step hydration reaction that
converts an alkene into
an alcohol. The process
results in the addition of a
hydrogen and
a hydroxal group where the
double bond had been.
Hydroboration–oxidation is
an anti-Markownikov
reaction, with the hydroxyl
group attaching to the less-
substituted carbon.
The general form of the
reaction is as follows:
Tetrahydrofuran(THF) is the
archetypal solvent used for
hydroboration.

Hydroformylation of Alkenes
Lower molecular weight olefins react with
carbon monoxide and hydrogen in the
presence of a catalyst in a reaction called
hydroformylation or the oxo reaction.
The resulting aldehyde is subsequently
hydrogenated to form an alcohol.
Industrial preparation
of alcohols:
o Preparation of
methanol:
By catalytic reduction of carbon
monoxide:
CO+2H2  CH3OH
Reaction occurs in the presence of
ZnO+Cr2O3 at 450 degree celsius and
at 200 atm pressure.
Procedure:
First of all a mixture of carbon monoxide
and hydrogen is purified.It is
compressed under a pressure of 200
atmosphere and taken into reaction
chamber by means of coiled pipes.Here
the catalyst is heated upto 450-500
degree celsius.Gases react to form
methanol vapours.These vapours are
passed through a condenser to get
methanol.Unreacted gases are recycled
through compresser to reaction
chamber.
Here is the flow sheet diagram for the
manufacturing

Preparation of ethanol:
Ethanol is prepared on indutrial scale world
over,by the process of fermentation.

Fermentation:
Fermentation is a biochemical
process which occurs in the
presence of certain enzymes
secreted by microorganism
such as yeast.
Ethanol is prepared by
fermentation of molassaes
and starch.
From molasses:
Molasses is a residue begotten from sugar
 

cane processing, molasses is the mother

 liquor left after crystallization of
sugarcane juice.It undergoes fermentation
in the presence of enzymes present in
yeast to give ethanol.

From starch:
How we can distinguish methanol and
ethanol?
Ethanol gives iodiform with iodine in the
presence of NaOH.Formation of yellow crystals
indicates that the alcohol is ethanol.
C2H5OH+4I2+6NaOHCHI3+HCOONa+
5NaI+5H2O
Methanol does not give this reaction.
CH3OH+I2+NaOHNo yellow
precipitates.

REACTIONS OF ALCOHOLS:
Alcohols reacts with other reagents in two ways
1.Reactions in which C-O bond breaks
If nucleophile(A nucleophile is electron rich species and donates
electron pairs to electron deficient species)attacks,it is the C-O

bond which breaks.

The order of reactivity of alcohols when C-O

bond breaks;
Tertiary alcohols>Secondary alcohols>primary
alcohols
Example:
C2H5OH+SOCL2C2H5CL+SO2+HCL
Reaction iccurs in the presence of pyridine.
C2H5OH+HNH2C2H5NH2+H2O
Reaction occurs in the presence of ThO2.
2.Reactions in which O-H bond breaks
If an eelectrophil(Electrophiles are electron deficient species and
can accept an electron pair from electron rich species) attacks on

alcohol, it is the. O-H bond which breaks

The order of reactivity of alcohols when O-H

bond breaks;
CH3OH>Primary>secondary>Tertiary
Example:

Reaction with grignard reagent:

Reaction with sodium metal:

Some other reactions of alcohols:

Oxidation of alcohols:
CH3CH2OH+[O]CH3CHO+H2O
Reaction occurs in the presence of
K2Cr2O7 and H2SO4 to form ethanal.
Formation of ethene:
CH3CH2OHCH2=CH2+H2O
Reaction occurs in the presence of
conc.H2SO4 at 180°C.
Formation of ether:
2C2H5OHC2H5OC2H5+H2O
 Reaction occurs in the presence of
conc.H2SO4 at 140°C.

 Reaction mechanism of
alcohols
Alcohols To Alkyl Chlorides With
SOCl2 – The Mechanism
As you might have guessed, conversion of
alcohols to alkyl halides proceeds through a
substitution reaction – specifically, an SN2
mechanism. The first step is attack of the
oxygen upon the sulfur of SOCl2, which
results in displacement of chloride ion. This
has the side benefit of converting the alcohol
into a good leaving group: in the next step,
chloride ion attacks the carbon in SN2
fashion, resulting in cleavage of the C–O
bond with inversion of configuration. The
HOSCl breaks down into HCl and sulfur
dioxide gas, which bubbles away.
Reaction with PCl3

Alcohols react with liquid phosphorus(III)

chloride (also called phosphorus
trichloride) to make chloroalkanes.
In the first figure, PCl3 accepts a lone pair
showing its acidic character and
expelling Cl −tive out. 
Reaction with PCl5
Solid phosphorus(V) chloride (phosphorus
pentachloride) reacts violently
with alcohols at room temperature,
producing clouds of hydrogen chloride gas.
THE END