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Question 51 of 69

Q.Nitromethane condenses with acetaldehyde to give :

(a) 2-nitro-1-propanol
(b) Nitro propane
(c) 3-nitro propanol
(d) 1-nitro-2-propanol
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2018MCQ· 1mImportance★★★★★
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Nitromethane's α\alpha-hydrogens (on the carbon bearing −NO2-NO_2) are acidic because the resulting carbanion is stabilised by the strongly electron-withdrawing nitro group. Under mild base, this carbanion undergoes a nitroaldol (Henry) condensation, attacking the electrophilic carbonyl carbon of acetaldehyde.

Mechanism: −CH2NO2^-CH_2NO_2 (from CH3NO2CH_3NO_2) attacks CH3CHOCH_3CHO's carbonyl carbon, giving the alkoxide CH3−CH(O−)−CH2NO2CH_3-CH(O^-)-CH_2NO_2, which is protonated to CH3−CH(OH)−CH2NO2CH_3-CH(OH)-CH_2NO_2. Numbering this propanol chain from the nitro-bearing end: C1 = CH2NO2CH_2NO_2, C2 = CH(OH)CH(OH), C3 = CH3CH_3 — giving 1-nitropropan-2-ol, i.e. 1-nitro-2-propanol. Option (a), 2-nitro-1-propanol, places the substituents on the wrong carbons (woul …

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