JEE Main 2020 · 4 September · morning · Single correct · +4 / −1
An organic compound (A) (molecular formula C₆H₁₂O₂) was hydrolysed with dil. H₂SO₄ to give a carboxylic acid (B) and an alcohol (C). ‘C’ gives white turbidity immediately when treated with anhydrous ZnCl₂ and conc. HCl. The organic compound (A) is :
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (d)
Solution
Chemistry ma’am · 3 steps
Instant Lucas turbidity means a tertiary alcohol, so pick the ester whose alcohol part is tert-butyl.
- Ester hydrolysis. All four options are esters of formula C₆H₁₂O₂. Dilute acid splits an ester RCOOR' into the acid RCOOH and the alcohol R'OH. So alcohol C comes from the group on the single-bonded oxygen.
- Read the Lucas test. Anhydrous ZnCl₂ and conc. HCl turn the alcohol into an insoluble alkyl chloride through a carbocation, and this chloride makes the mixture cloudy. A tertiary carbocation is the most stable, so a tertiary alcohol turns cloudy at once. A secondary alcohol takes about 5 minutes, and a primary alcohol shows no turbidity at room temperature.
Option Ester Alcohol C Type Lucas test (a) sec-butyl ethanoate butan-2-ol 2° turbid in about 5 min (b) propyl propanoate propan-1-ol 1° no turbidity at room temperature (c) isobutyl ethanoate 2-methylpropan-1-ol 1° no turbidity at room temperature (d) tert-butyl ethanoate 2-methylpropan-2-ol, (CH₃)₃COH 3° turbid immediately - So. Only (d) gives a tertiary alcohol. Hydrolysis gives ethanoic acid (B) and tert-butyl alcohol (C), which turns cloudy at once, so A is tert-butyl ethanoate.
The idea to keep. In the Lucas test, turbidity tracks carbocation stability: tertiary turns cloudy at once, secondary in about 5 minutes, primary not at room temperature. For an ester, check the alkyl group on the oxygen.
Answer from the NTA final answer key. Solution by PrepWiser.