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★★★★★
74% · 51/69 Questions
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Start your 14-day free trial to unlock the full solution →Nitromethane's -hydrogens (on the carbon bearing ) 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: (from ) attacks 's carbonyl carbon, giving the alkoxide , which is protonated to . Numbering this propanol chain from the nitro-bearing end: C1 = , C2 = , C3 = — 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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