Chemistry - Carbonyl compounds Question with Solution | TestHub
An organic compound P has molecular formula C₉H₁₃NO and it can be resolved into enantiomers. P does not decolorize bromine water solution. P on refluxing with dilute H₂SO₄ yields another resolvable compound Q (C₉H₁₄O₃), which gives effervescence with NaHCO₃. Q on treatment with NaBH₄ yields R (C₉H₁₆O₃), which on heating with concentrated H₂SO₄ yields ester S (C₉H₁₄O₂).
Find out correct structure of compound P is:
Options:
Answer:
Solution:
P has formula C₉H₁₃NO and shows optical isomerism, so it must have a chiral center; also it does not decolorize Br₂ water, so no C=C (non-aromatic or saturated system).
On reflux with dilute H₂SO₄, P → Q (C₉H₁₄O₃) that gives effervescence with NaHCO₃, confirming –COOH group formation ⇒ P contains a group hydrolysable to acid (like –CN).
NaBH₄ reduces Q to alcohol R, and further heating with conc. H₂SO₄ gives an ester, consistent with –COOH → –CH₂OH transformation.
Only Option C satisfies: presence of –CN (→ COOH), ketone (→ alcohol), and chiral center.