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2-Nitropropane reacts with formaldehyde in the presence of NaOH (Henry reaction). The major organic product obtained is:

1. 2-Nitro-2-methylpropan-1-ol (CH3)2C(NO2)CH2OH
2. 2-Nitropropan-1-ol CH3CH(NO2)CH2OH
3. 1-Nitropropan-2-ol CH3CH(OH)CH2NO2
4. 2-Nitro-1,3-propanediol O2N-CH(CH2OH)2

Correct answer: 2-Nitro-2-methylpropan-1-ol (CH3)2C(NO2)CH2OH

Solution

NaOH abstracts the acidic alpha-H from (CH3)2CHNO2 at the carbon bearing NO2, generating the resonance-stabilised nitronate anion (CH3)2C^(-)(NO2). This nucleophile attacks formaldehyde (HCHO) to give the beta-nitroalcohol (CH3)2C(NO2)CH2OH after protonation.

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