By:

Barez
Bryar
hazhir
Stanislao Cannizzaro
 was an Italian chemist
 13 July 1826 – 10 May 1910 (aged 83)
 He entered the university there with the intention of making medicine
his profession, but he soon turned to the study of chemistry
 Cannizzaro became professor of chemistry at the University of Genoa
is one of the largest universities in Italy
 he spent ten years studying aromatic compounds
 Cannizzaro provided a new understanding of chemistry
 Cannizzaro reaction

strong
Conc. base
Benzaldehyde Acid salt alcohol
Note:
There must be
no α hydrogen

Cannizzaro reaction is a nucleophilic acyl substitution

reaction of aldehydes and ketones
Cannizzaro Reaction mechanism
Dissolve 1gm – KOH in 1 ml H2O

Cool the solution to the room

temperature

shake
Until permanent 1ml benzaldehyde
emulsion is formed
Allow the tube to stand
For a long while
(overnight)
Crystallization occur
Now the reaction have
been completed
2 ml H2O
Extract 3 times
Shake gently to avoid forming emulsion
This will remove unreacted Shake it till all crystals
benzaldehyde and benzyl alcohol dissolve
We will not isolate Benzyl alcohol
4ml ethyl acetate solution
The reduction product
 3ml
The alkaline aqueous solution Conc.HCl
Aqueous layer

3ml
water
Stirring vigorously

Cool in ice bath 3gm

Crushed ice

Collect the crystal of benzoic acid

Determined % of yield
Question answers :
What is the difference between the Cannizzaro reaction and an aldol reaction ? Give and example
Cannizzaro reaction aldol reaction
can only occur in an aldehyde with no α -hydrogens needs α -hydrogens next to the functional group in order to proceed

One of these hydrogen atoms is removed to form the enolate

Why do we acidify the aqueous layer ?

Organic acids are currently dissolved in a basic aqueous solution, because the acid
forms a salt, an ionic form. When you make the aqueous solution acidic,
the organic acids no longer remain dissolved because they are no longer ionic and
usually precipitate out of solution. This process is called acidification