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JEE Main · 2020 · 04 Sep 2020 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

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An organic compound (A) (molecular formula ) was hydrolysed with dil. to give a carboxylic acid (B) and an alcohol (C). 'C' gives white turbidity immediately when treated with anhydrous and conc. HCl. The organic compound is:
  1. (A)(see structure)
    ✓ Correct
  2. (B)(see structure)
  3. (C)(see structure)
  4. (D)(see structure)

Answer: (A)

Solution

Compound A, , hydrolyses to a carboxylic acid and an alcohol, which marks it as an ester. The alcohol gives an immediate turbidity with the Lucas reagent ( with concentrated ), a response seen only with a tertiary alcohol. The ester that fits is tert-butyl acetate, since its hydrolysis releases acetic acid together with the tertiary alcohol tert-butanol, which reacts at once with the Lucas reagent.

JEE Main · 2020 · 04 Sep 2020 · Shift 1 · Single correct option

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