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A mixture of (CH(3))(3)C-CHO and HCHO on...

A mixture of `(CH_(3))_(3)C-CHO` and HCHO on heating with aqueous NaOH solution will give:

A

`HCOONa+(CH_(3))_(3)C-CH_(2)OH`

B

`(CH_(3))_(3)C-COONa+CH_(3)OH`

C

`HCOONa+(CH_(3))_(3)C-COONa`

D

`CH_(3)OH+(CH_(3))_(3)C-CH_(2)OH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reaction between the given aldehydes, `(CH₃)₃C-CHO` (which is 2-methylbutanal) and HCHO (formaldehyde), when heated with aqueous NaOH. ### Step-by-Step Solution: 1. **Identify the Aldehydes**: The two aldehydes in the mixture are: - `(CH₃)₃C-CHO` (2-methylbutanal) - HCHO (formaldehyde) 2. **Check for Alpha Hydrogens**: - 2-methylbutanal has no alpha hydrogen because the carbon adjacent to the carbonyl group is attached to three methyl groups. - Formaldehyde (HCHO) has alpha hydrogens. 3. **Determine the Reaction Type**: - Since 2-methylbutanal does not have alpha hydrogens, it cannot undergo an aldol condensation. - However, formaldehyde can participate in the Cannizzaro reaction, which occurs in the absence of alpha hydrogens. 4. **Cannizzaro Reaction**: - In the Cannizzaro reaction, one molecule of aldehyde is oxidized to a carboxylic acid, while another molecule is reduced to an alcohol. - Here, formaldehyde (HCHO) will undergo the Cannizzaro reaction. 5. **Reaction Mechanism**: - The hydroxide ion (from NaOH) will attack the carbonyl carbon of formaldehyde, leading to the formation of a tetrahedral intermediate. - This intermediate will then collapse, resulting in the transfer of a hydride ion to another molecule of formaldehyde. - One molecule of formaldehyde will be oxidized to formic acid (HCOOH), and the other will be reduced to methanol (CH₃OH). 6. **Final Products**: - The final products of the reaction will be: - Formic acid (HCOOH) from the oxidation of formaldehyde. - Methanol (CH₃OH) from the reduction of formaldehyde. ### Conclusion: The mixture of `(CH₃)₃C-CHO` and HCHO on heating with aqueous NaOH will yield: - Formic acid (HCOOH) - Methanol (CH₃OH)
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