Question Details

For the reaction sequence given below, the correct statement(s) is(are)

Options

A

Both X and Y are oxygen containing compounds

B

Y on heating with CHCl3/KOH forms isocyanide

C

Z reacts with Hinsberg’s reagent.

D

Z is an aromatic primary amine.

Show Answer

Correct Answer :

Option A

Both X and Y are oxygen containing compounds

Solution :

The given reaction sequence proceeds through the following steps:

Step 1: Oxidation of Tetralin to form X
When tetralin (1,2,3,4-tetrahydronaphthalene) is treated with acidic potassium permanganate (KMnO4/H+) under heating (Δ), the non-aromatic ring undergoes oxidative cleavage to yield phthalic acid (benzene-1,2-dicarboxylic acid).
Subsequently, heating phthalic acid with ammonia (NH3) results in the loss of two water molecules (-2H2O), forming phthalamide:
C6H4(COOH)2+2NH3C6H4(CONH2)2+2H2O
Thus, X is phthalamide, which contains oxygen (carbonyl groups).

Step 2: Conversion of X to Y
(i) Strong heating of phthalamide (X) results in the elimination of a molecule of ammonia (NH3) to form phthalimide.
(ii) Treating phthalimide with ethanoic (alcoholic) potassium hydroxide (KOH) deprotonates the imide nitrogen, producing potassium phthalimide.
(iii) Nucleophilic substitution of potassium phthalimide with an alkyl bromide (R-Br) yields N-alkylphthalimide:
Thus, Y is N-alkylphthalimide, which is also an oxygen-containing compound.

Step 3: Hydrolysis of Y to form Z
Basic hydrolysis of N-alkylphthalimide (Y) using sodium hydroxide (NaOH) yields sodium phthalate (the aromatic compound) and an aliphatic primary amine (Z, R-NH2). This entire process represents the Gabriel Phthalimide Synthesis.

Therefore, both compound X (phthalamide) and compound Y (N-alkylphthalimide) contain oxygen.

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