Experimant No 06 :- To Synthesize Bezoic Acid from Benzaldehyde.
Reference:
Vogel's Textbook of practical organic chemistry revised by B. S.
Furniss, a. J Hannaford.
P. W. G.
Smith, A. R. Tatchell.
Fifth Edition. ELBS. 1989.
page no - 1029.
Requirements:
Apparatus
- Beaker, Conical Flask, Water Bath Vessel, Reagent Bottle, Separatory Funnel,
Funnel. Measuring Cvlinder. Pipette, Stirrer, Spatula, Etc
Chemicals -
Potassium Hydroxide, Ice, Benzaldehyde, Ether, Sodium Metabisulphite, Sodium
Carbonate, Hydrochloric Acid. Instrument
- Hot Air Oven. Vacuum Pump, Melting
Point Apparatus.
Principle:
maticaldehydes do not contain alpha hydrogen atomseg. Formaldehyde and bonatachar under the
influence of strong aqueous or al ammeous or alcoholic alkali undergoes simultaneous
oxidation and on yielding the alcohol and corresponding carboxylate salt.
This
dismutation or disproportionation reaction is known as the Cannizzaro
reaction. The mechanism of the reaction
involves the production of the anion (1) which may transfer a hydride ion to a
carbonyl carbon atom in another aldehyde molecule. The reaction is completed by a proton
transfer toyield the carboxylate anion and the alcohol.
The
reaction is illustrated here by the conversion of benzaldehyde into benzoic
acid and benzyl alcohol.
Reaction:-
Procedure:
I.
Dissolve 29 g of potassium hydroxide in
27 ml of water in a beaker or conical flask, and cool the solution to about 20C
in ice water. Pour this solution in
250ml reagent bottle and add 32g (30 ml, 0. 3 mol) of pure benzaldehyde. Cork bottle and shake it vigorously until it
has been converted into thickemulsion and allow the bottle to stand overnight.
II.
Add just sufficient water (about 105 ml) to
dissolve the potassium benzoate which formed.
Pour this mixture into a separatory funnel, rinse reagent bottle with
about 30 ml of ether and add this ether to the solution in the funnel.
III.
Shake the solution in order to
thoroughly extract the benzyl alcohol with the ether, separate the lower
aqueous solution and carry out further extractions each with about 25 ml of
ether. Save the aqueous solution.
IV.
Add this aqueous solution into a mixture of 80
ml of concentrated hydrochloric acid and 80 ml of water and about 100 g of
crushed ice.
V.
Filter the precipitated benzoic acid at
the pump, wash it with little cold water, drain and recrystallize from boiling
water.
VI.
The yield of benzoic acid (colorless crystal),
m. p 121 ° C, is 13. 5 g (79%)
Result:-
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