Question
Question: The Cannizzaro reaction is not given by; \( A) \) Formaldehyde \( B) \) Acetaldehyde \( C) ...
The Cannizzaro reaction is not given by;
A) Formaldehyde
B) Acetaldehyde
C) Benzaldehyde
Solution
Cannizzaro reaction can be defined as base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position. This reaction was named after its discoverer Stanislao Cannizzaro.
Complete answer:
Cannizaro reaction is a characteristic reaction of aldehydes lacking α - hydrogen. The reaction involves disproportionation (oxidation and reduction) of aldehyde in the presence of a strong base forming carboxylic acid and alcohol.
Now, coming back to our question.
We have three aldehydes and we have to tell which one will not give Cannizzaro reaction.
-Formaldehyde ( HCHO )
It doesn’t have α - hydrogen and will not form an enolate . Thus, Formaldehyde will undergo Cannizzaro reaction very efficiently. It will be disproportionate to give acid and alcohol.
-Acetaldehyde ( CH3CHO )
Acetaldehyde is having α - hydrogen. In the presence of base it will form an enolate ion and will undergo Aldol Condensation reaction. Thus, Acetaldehyde will not show Cannizzaro reaction.
-Benzaldehyde ( C6H5CHO )
Benzaldehyde also lacks α - hydrogen. Thus, Benzaldehyde will also undergo Cannizzaro reaction.
Hence, option B) Acetaldehyde is correct.
Additional Information:
The nucleophile ( OH− ) attacks the carbonyl carbon of aldehyde causing the disproportionation reaction of aldehyde. Crossed Cannizzaro reaction is used in order to avoid low yields. In Cross Cannizzaro two different aldehydes lacking α - hydrogens are made to undergo the reaction.
Note:
In order to check which aldehyde will give Cannizzaro reaction, we just have to check the α - hydrogens on aldehyde. The one having α - hydrogen will undergo Aldol Condensation instead of Cannizzaro reaction. Examples of aldehydes without α - hydrogen include Vanillin, Benzaldehyde, Formaldehyde etc.