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Treatment of propionadehyde with dilute ...

Treatment of propionadehyde with dilute NaOH gives :

A

`CH_(3)CH_(2)COOCH_(2)CH_(2)CH_(3)`

B

`CH_(3)CH_(2)CH(OH)CH(CH_(3))CHO`

C

`CH_(3)CH_(2)CH(OH)CH_(2)CH_(2)CHO`

D

`CH_(3)CH_(2)COCH_(2)CH_(2)CHO`

Text Solution

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The correct Answer is:
To solve the problem of what happens when propionaldehyde (propionaldehyde is CH3CH2CHO) is treated with dilute NaOH, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Structure of Propionaldehyde**: - Propionaldehyde has the structure CH3CH2CHO, where the aldehyde group (CHO) is at the end of the carbon chain. 2. **Recognize the Reaction Type**: - The treatment of propionaldehyde with dilute NaOH suggests an aldol condensation reaction. In this reaction, aldehydes with alpha-hydrogens can undergo self-condensation. 3. **Identify the Alpha Hydrogen**: - The alpha carbon in propionaldehyde is the second carbon (CH2), which has two hydrogen atoms (H). These alpha hydrogens are crucial for the reaction. 4. **Formation of Enolate Ion**: - The dilute NaOH provides hydroxide ions (OH-), which can abstract one of the alpha hydrogens from the propionaldehyde, forming an enolate ion. The reaction can be represented as: \[ CH3CH2CHO + OH^- \rightarrow CH3CH2C(=O^-)H \] 5. **Nucleophilic Attack**: - The enolate ion (which has a negative charge) acts as a nucleophile and attacks the carbonyl carbon of another propionaldehyde molecule. This leads to the formation of a β-hydroxy aldehyde (aldol product): \[ CH3CH2C(=O^-)H + CH3CH2CHO \rightarrow CH3CH2C(OH)(CH2CHO)H \] 6. **Final Aldol Product**: - The resulting β-hydroxy aldehyde can be represented as: \[ CH3CH2CH(OH)CH2CHO \] - This product has a hydroxyl group (-OH) on the beta carbon relative to the aldehyde group. 7. **Condensed Structural Formula**: - The final condensed structural formula of the aldol product is: \[ CH3CH2CH(OH)CHO \] ### Conclusion: The treatment of propionaldehyde with dilute NaOH results in the formation of a β-hydroxy aldehyde, specifically 3-hydroxybutanal.
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