JEE Advanced 2024 Chemistry question
Complete reaction of acetaldehyde with excess formaldehyde, upon heating with conc. NaOH solution, gives **P** and **Q**. Compound **P** does not give Tollens' test, whereas **Q** on acidification gives positive Tollens' test. Treatment of **P** with excess cyclohexanone in the presence of catalytic amount of *p*-toluenesulfonic acid (PTSA) gives product **R**. Sum of the number of methylene groups () and oxygen atoms in **R** is .
Solution
Three crossed aldol additions of formaldehyde to the α-carbon of acetaldehyde give , and a crossed Cannizzaro reaction with formaldehyde reduces it to pentaerythritol **P** = , with sodium formate **Q** (formic acid reduces
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