Which of the following compounds can undergo both Cannizzaro reaction as well as Aldol condensation ?

Options

A. HCHO
B. `C_(6)H_(5)CHO`
C. `CH_(3)CHO`
D. `(CH_(3))_(2)CHCHO`

Explanation

To determine which compound can undergo both the Cannizzaro reaction and Aldol condensation, we need to analyze the conditions required for each reaction and the structures of the given compounds.

### Step-by-Step Solution:

1. **Understand the Cannizzaro Reaction**:
- The Cannizzaro reaction occurs with aldehydes that do not have alpha hydrogens. In this reaction, one molecule of the aldehyde is oxidized to a carboxylic acid, while another is reduced to an alcohol.

2. **Understand the Aldol Condensation**:
- Aldol condensation requires aldehydes or ketones that have at least one alpha hydrogen. In this reaction, two molecules of the aldehyde or ketone react to form a β-hydroxy aldehyde or ketone, which can further dehydrate to form an α,β-unsaturated carbonyl compound.

3. **Analyze the Given Compounds**:
- **Option A: HCHO (Formaldehyde)**
- Structure: HCHO has no alpha hydrogen (since it is the simplest aldehyde).
- Conclusion: Can undergo Cannizzaro reaction but NOT Aldol condensation.

- **Option B: Benzaldehyde (C6H5CHO)**
- Structure: Benzaldehyde has no alpha hydrogen (the carbon adjacent to the carbonyl is part of the benzene ring).
- Conclusion: Can undergo Cannizzaro reaction but NOT Aldol condensation.

- **Option C: Acetaldehyde (CH3CHO)**
- Structure: Acetaldehyde has three alpha hydrogens (the methyl group provides three hydrogens).
- Conclusion: Can undergo Aldol condensation but NOT Cannizzaro reaction.

- **Option D: An alpha mono-alkylated aldehyde (e.g., CH3CH(CH3)CHO)**
- Structure: This compound has one alkyl group and one hydrogen on the alpha carbon.
- Conclusion: Can undergo both Cannizzaro reaction (due to the absence of alpha hydrogen) and Aldol condensation (due to the presence of alpha hydrogen).

4. **Final Conclusion**:
- The correct answer is **Option D**, as it is the only compound that can undergo both the Cannizzaro reaction and Aldol condensation.