18551507-019 CHEM-312 Lab Manual
18551507-019 CHEM-312 Lab Manual
18551507-019 CHEM-312 Lab Manual
Semester spring-2021
Submission date (31-03-2021)
Submitted to
Dr. Ghulam Mustafa
Submitted by
Rukhsana Yasmin
Roll no # 18551507-019
BS chemistry VI (A)
Department 0f Chemistry
University 0f Gujrat
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EXPERIMENT NO# 1
Synthesis of p-chlorobenzoic acid and p- chlorobenzyl alcohol from p-
chlorobenzaldehyde through Cannizzaro’s reaction
Theory
The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction
that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the
alpha position. It means aldehydes with no alpha-hydrogen give this type of reaction.
Disproportionation reactions are those in which half of the reactant molecule is oxidized and half
are reduced. In this case the half aldehyde is oxidized to carboxylic acid and other half is reduced
to alcohol. The reaction is carried out in the presence of strong base like NaOH or KOH.
General reaction
Here the oxidation product is a salt of a carboxylic acid and the reduction product is an alcohol.
Reaction mechanism
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The reaction mechanism involves a nucleophilic acyl substitution on an aldehyde, with the
leaving group simultaneously attacking another aldehyde in the second step. First, hydroxide
attacks a carbonyl. The resulting tetrahedral intermediate then collapses, re-forming the carbonyl
and transferring hydride to attack another carbonyl. In the final step of the reaction, the acid and
alkoxide ions formed exchange a proton. In the presence of a very high concentration of base, the
aldehyde first forms a doubly charged anion from which a hydride ion is transferred to the
second molecule of aldehyde to form carboxylate and alkoxide ions. Subsequently, the alkoxide
ion acquires a proton from the solvent.
Principle
Two molecles of p-chlorobenzaldehyde reacts with the base KOH and it undergo redox reaction
in which half reactant molecule is oxidized and half is reduced. The resulting product is p-
chlorobenzoic acid and p-chlorobenzyl alcohol.
Material required
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Magnetic bar
Separatory funnel
Chemicals required
p-chlorobenzaldehyde
Methanol
Distilled water
Dichloromethane
Potassium hydroxide KOH
Sodium sulfate
Experimental Procedure
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6. Now by using anhydrous sodium sulfate the organic layer is dried to remove
any moisture and by using rotary evaporator the dichloromethane in organic
layer is evaporated.
7. In organic layer the crude p-chlorobenzyl alcohol is purified by
recrystallizing it by using 3 mL of 4% acetone in hexane.
8. The aqueous layer is cooled in ice bath after acidified by adding 3 mL of
conc. HCl. White precipitates are collected by vacuum filtration, washed the
filtered cake using 5 mL water and dry the product in air and then
recrystallize in methanol.
9. Check the melting points of products and then calculate the %age yield by
take weights of products.
Mass of p-chlorobenzaldehyde = 2g
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Melting point of organic layer = 71°C
actual yield
% yield of p-chlorobenzoic acid = Theoretical yield x 100
0.89 g
= 1.10 g x 100
= 81%
actual yield
% yield of p- chlorobenzyl alcohol = Theoretical yield x 100
0.82 g
= 0.99 g x 100
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Identification of peaks
In this spectra of p- chlorobenzoic acid the different functional groups have different wavelength
peaks.
Identification of peaks
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In this spectra of p- chlorobenzyl alcohol the different functional groups have different
wavelength peaks
Results
The crystals of p-chlorobenzyl alcohol and p-
chlorobenzoic acid have been formed having % yield 82%
and 81% respectively.
Refrences
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organi
c_Chemistry)/Reactions/Organic_Reactions/Cannizzaro_Reaction
http://www.rsc.org/suppdata/books/184973/9781849739634/bk9781849739634-chapter
%2017.pdf
http://www.studou.com
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