Single correct option
2-Methylpropanal is heated with excess aqueous formaldehyde in the presence of concentrated NaOH. The organic product is
- A. 2,2-dimethylpropane-1,3-diol
- B. 3-hydroxy-2,2-dimethylpropanal
- C. sodium 3-hydroxy-2,2-dimethylpropanoate
- D. 2-methylpropan-1-ol
Show answer and solution
Answer: (A) 2,2-dimethylpropane-1,3-diol
2-Methylpropanal has one -hydrogen, so with it undergoes a crossed aldol addition to give . This product has no -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 , 2,2-dimethylpropane-1,3-diol (neopentyl glycol).
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