Cannizzaro Reaction
Part II
Name of Experiment : Cannizzaro Reaction.
Aim of Experiment : Isolation of Benzoic Acid &
Benzyl alcohol
Procedure :
1- Add 30 mL of H2O to completely dissolve the
Potassium benzoate.
2- Pour the liquid into a separatory funnel.
3- Rinse the bottle with 10 mL of ether & add this
ether to the solution in the separatory funnel.
4- Shake well & separate the lower aq. layer from
upper ethereal layer.
5- Extract the aq. layer with 10 mL ether. (two times)
A- Isolation of Benzyl alcohol :
1- Combine the ethereal extracts.
2- Distil the ether on a water bath until 10 – 15 mL
of liquid remains.
3- Cool the remaining liquid and transfer it to a
separatory funnel.
4- Shake the ether layer with 3 mL of saturated
Sodium bisulfite solution, NaHSO3 *, & separate
the oily liquid from the aq. NaHSO3 solution,
( two times ).
O O Na OH
Na HSO3
C H C H C H
SO3H SO3 Na
α-hydroxy benzyl
sodium sulfonate
* To remove any unreacted
Benzaldehyde which may be present.
5- Wash the oily liquid with 5 mL of 10 % Na2CO3 **
Na2CO3 + 2 NaHSO3 CO2 + H2O + 2 Na2SO3
excess
** To ensure complete removal of unreacted NaHSO3
6- Wash with 5 mL H2O .
7- Dry the oily liquid over anhydrous Magnesium
sulfate, Mg2SO4 .
8- Filter the solution into a small distilling flask &
distil off the ether on a water bath.
9- Attach a short air – cooled condenser & distil the
Benzyl alcohol .
10- Collect the material boiling at 204 – 207 oC .
B- Isolation of Benzoic acid :
1- Pour the alkaline aqueous layer with stirring
into a mixture of 20 mL conc. HCl + 20 mL H2O
+ 20g of crushed ice .
O O
C O K + HCl C OH + KCl
Potassium benzoate Benzoic acid
( Soluble in water ) ( Insoluble in cold water )
2- Filter the ppt. ( Benzoic acid ) at the pump.
3- Wash the ppt. with little cold H2O .
4- Drain & recrystallize from boiling H2O .
( colorless crystals of Benzoic acid, m.p. 121 oC ) .
1- In extraction by ether & water , which one of them
will be the upper layer ? And why ?
2- How can we get rid of the excess unreacted
Benzaldehyde ?
3- Explain why , 10% Na2CO3 solution is used for
washing the ether layer ?
4- How can we purify the synthesized Benzoic acid ?
Explain .
* Robert T. Morrison , Robert N. Boyd: “ Aldehydes and
Ketones” . Organic Chemistry, (6th) edition , Prentice -
Hall Inc.
* Carey, Francis A.: “Aldehydes and Ketones: Nucleophilic
Addition to the Carbonyl Group ” . Organic Chemistry
(6th) edition, McGraw-Hill companies, Inc.
* Samira Finjan Hassan, Amer Nadem, May Mohammed
Jawad , A Laboratory manual on Practical Medical
Chemistry for 4th year students, University of Baghdad
, College of Pharmacy , Department of Pharmaceutical
Chemistry, 2010.
* Vogel, Arthur,Textbook of Organic Chemistry,4th
edition.
* John E. McMurry,Organic Chemistry, 8th edition, 2012
