Question

An organic compound (A) `C_(6)H_(12)O_(3)` on treatment with concentrated `H_(2)SO_(4)` gives `CO, H_(2)O` and (B). Compound (B) can be prepared by passing vapours of 1-pentanol Over heated copper at 570 K. Compound (A) on heating gives (C), `C_(12)H_(20)O_(4)`. Give the structures of (A) to ( C) with proper reasoning.

Answer 1

Compound (B) must be pentanol because 1t is prepared by passmg vapours of 1-pentanol over heated copper
`underset("Pentan -1-ol ")(CH_(3)(CH_(2))_(3)CH_(2)OH)underset(570 K)overset(Cu)tounderset("Pentanal")(CH_(3)(CH_(2))_(3)-CHO+H_(2)O)`
Compound (A) gives `CO_(2)` and `H_(2)O` on treatment with conc. `H_(2)SO_(4)`. Thus, compound (A) must be`alpha` -hydroxy acid