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JEE Main 2018 · Chemistry · Carbonyl Compounds, Carboxylic Acids and Amines · hard

2-Methylpropanal is heated with excess aqueous formaldehyde in the presence of concentrated NaOH. The organic product is

Single correct option

2-Methylpropanal is heated with excess aqueous formaldehyde in the presence of concentrated NaOH. The organic product is
  1. A. 2,2-dimethylpropane-1,3-diol
  2. B. 3-hydroxy-2,2-dimethylpropanal
  3. C. sodium 3-hydroxy-2,2-dimethylpropanoate
  4. D. 2-methylpropan-1-ol
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Answer: (A) 2,2-dimethylpropane-1,3-diol

2-Methylpropanal has one α\alpha-hydrogen, so with HCHO\mathrm{HCHO} it undergoes a crossed aldol addition to give HOCH2C(CH3)2CHO\mathrm{HOCH_2C(CH_3)_2CHO}. This product has no α\alpha-hydrogen, so in concentrated alkali with excess formaldehyde it undergoes a crossed Cannizzaro reaction. Formaldehyde, the better hydride donor, is oxidised to formate, while the hindered aldehyde is reduced to HOCH2C(CH3)2CH2OH\mathrm{HOCH_2C(CH_3)_2CH_2OH}, 2,2-dimethylpropane-1,3-diol (neopentyl glycol).
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