Date- 03-05-2021

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REACTION OF THE DAY_06

Chemistry
Cannizzaro Reaction
Cannizzaro reaction: Aldehydes which donot have any -H atom such as HCHO and C6H5CHO undergo self
oxidation and self reduction (i.e., disproportionation) on treatment with conc. alkali. In this one molecule is reduced
to alcohol and the other is oxidised to salt of carboxylic acid.
conc. KOH
HCHO  HCHO   CH3 OH  HCOOK
CHO CHO CH2OH COONa
conc. NaOH
+ +

CH3
CH3 C CHO can also undergo Cannizzaro reaction, as it does not have any -H atom
CH3

Mechanism of the Cannizzaro Reaction

Note: Hydride ion ( H ) transfer is the rate determining step in Cannizzaro reaction.

-Keto aldehydes give the product of an intramolecular disproportionation in excellent yields.

(1)
 Cross Cannizzaro reaction: Cannizzaro reaction taking place between two different aldehydes (both not having
any -H atom) is cross Cannizzaro reaction.

CH3O CHO + HCHO + NaOH (50%) CH3O CH2OH + HCOONa

In the crossed Cannizzaro reaction the more reactive aldehyde gets oxidised and less reactive aldehyde gets
reduced.



Try Yourself
1. Major products of the following reaction are:

CHO
i 50% NaOH
+ HCHO   
+
ii H3O

CH2OH CH2OH COOH

(1) HCOOH and (2) and

COOH
(3) CH3OH and (4) CH3OH and HCO2H

2. Consider the following reaction

C
i  alkali
CHO    Major Product (P)
+
ii H3O

The major product P is

OH
CH2OH
(1) + HCOOH (2) COOH

O OH
C
(3) CH2 – OH (4) CH2OH

(2)
3. The number of aldol reaction(s) that occurs in the given transformation is

OH OH
conc. aq. NaOH
CH3CHO + 4HCHO
HO OH
(1) 1 (2) 2
(3) 3 (4) 4
4. The major product of the following reaction sequence is

O
(i) HCHO (excess)/NaOH, heat
+
(ii) HCHO/H (catalytic amount)

O O O O OH

(1) (2)

HO O O O OH

(3) (4)

OH

5. What should be the product (A and B) of the following reaction

+
CHO Na NH

THF, 0°C
+ A+B

– +
CH2OH NH–OH COO Na CH2–OH

(1) + (2)
+

O +
Na
O +
Na
C N C N OH
CH2–OH
(3) (4)
+ +


Answer of Question Based on Birch Reduction
1. Answer (1)
2. Answer (2)
3. Answer (3)
4. Answer (4)
5. Answer (1)

(3)