An organic compound (A)(C5H7OCl) reacts rapidly with ethanol to give (B)(C7H12O2). (A) also reacts with water to produce an acid which reacts with bromine to give (C)(C5H8Br2O2). (B) on boiling with H2SO4 forms an acid (D). When (D) is oxidised with KMnO4, an acid (E)(C4H6O3) is produced. On mild heating, (E) gives (F)(C3H6O) which cannotb be oxidised by ammoniacal AgNO3. Identify the compounds (A) to (F).

Engineering

Chemistry

Preparation of Aldehyde and Ketones

Oxidation of aldehydes and ketones

Question

An organic compound (A)(C₅H₇OCl) reacts rapidly with ethanol to give (B)(C₇H₁₂O₂). (A) also reacts with water to produce an acid which reacts with bromine to give (C)(C₅H₈Br₂O₂). (B) on boiling with H₂SO₄ forms an acid (D). When (D) is oxidised with KMnO₄, an acid (E)(C₄H₆O₃) is produced. On mild heating, (E) gives (F)(C₃H₆O) which cannotb be oxidised by ammoniacal AgNO₃. Identify the compounds (A) to (F).

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(A) ⇒ C₅H₇OCl ; Degree of unsaturation : 2°
(B) ⇒ Degree of unsaturation : 2°

$\underset{C_{2} H_{7} OCI}{(A)} \overset{C_{2} H_{5} OH}{\to} \underset{C_{7} H_{12} O_{2}}{(B)} \to_{Boil}^{H_{2} {SO}_{4}} \underset{Acid}{(D)} \overset{{KMnO}_{4}}{\to} \underset{\underset{C_{4} H_{6} O_{3}}{Acid}}{(E)} \overset{∆}{\to} \underset{C_{3} H_{6} O}{(F)} \overset{Amm . {AgNO}_{3}}{\to} \underset{reaction}{NO}$

⇒ (F) (not, aldehyde mey be a ketone)

C₅H₈Br₂O₂ [This shows (C = C)]
(F) ⇒ Ketone (three C atoms) ; only ketone with three C atoms is acetone (CH₃ – CO – CH₃)

because keto acid on heating loses CO₂ and gives ketone.
$(D) \overset{[O]}{\to}$ Acid (E) C₄H₆O₃ [So, (D) contains (C = C)]

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