Question:

Consider the following sequence of reactions:
isopropyl benzene
The incorrect statement about compound \( z \) is:

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For iodoform test, the compound must have the group CH\textsubscript{3}–CO– attached to a non-aromatic carbon.
Updated On: Jun 4, 2025
  • \( z \) gives a yellow precipitate of \( \text{CHI}_3 \) with NaOH + \( \text{I}_2 \) solution.
  • \( z \) gives isopropyl alcohol on reduction with \( \text{H}_2 \) in the presence of Pd catalyst.
  • \( z \) on reaction with \( \text{CH}_3\text{MgBr} \) followed by hydrolysis gives \( 2^\circ \) alcohol.
  • \( z \) does not give positive test with Fehling’s reagent
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    The Correct Option is A

    Solution and Explanation

    Step 1: Reaction pathway
    Isopropyl benzene (cumene) on oxidation gives cumene hydroperoxide, which upon acid hydrolysis gives acetophenone: \[ \text{(CH}_3)_2CH{-}C_6H_5 \xrightarrow{O_2} \text{Cumene hydroperoxide} \xrightarrow{H^+} \text{Acetophenone} \] Step 2: Structure of \( z \)
    \[ z = \text{Acetophenone } (C_6H_5COCH_3) \] Step 3: Analyze each option \begin{itemize} \item[1.] Acetophenone does not give iodoform test (requires a methyl ketone attached to an aliphatic group, not aromatic) → Incorrect \item[2.] Acetophenone on catalytic hydrogenation gives isopropyl benzene → Correct \item[3.] Reaction with CH\textsubscript{3}MgBr gives tertiary alcohol → Correct \item[4.] Acetophenone is a ketone; it does not respond to Fehling’s test → Correct \end{itemize} %Quicktip
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