Hydrocarbon A (C 9 H 12 ) absorbs 3 equivalents of H 2 in the presence of Pd/C to yield B (C 9 H 18 ). A when treated with aqueous H 2 SO 4 in the presence of Hg(II) gives two isomeric ketones C and D . A upon oxidation with KMnO 4 gives a mixture of acetic acid and tricarboxylic acid E . Based on these data, structures for the compounds A - D are to be given and the reactions are to be written. Concept introduction: The degree of unsaturation can be calculated by comparing the molecular formula of compound given with that of its parent hydrocarbon. Both alkenes and alkynes yield alkanes by adsorbing H 2 in the presence of Pd catalyst. Alkynes require two equivalents of H 2 while alkenes require one equivalent of H 2 to give alkanes. Internal alkynes will yield a mixture of isomeric ketones when treated with aqueous H 2 SO 4 in the presence of mercury (II) if they are symmetrically substituted. When oxidized with KMnO 4 , monosubstituted carbons in both double and triple bonds get oxidized to carboxylic acids. To give: Based on the data given, the structures of A - D and to write the reactions.

Question

Hydrocarbon A has the formula C9H12 and absorbs 3 equivalents of H2 to yield B, C9H18, when hydrogenated over a Pd/C catalyst. On treatment of A with aqueous H2SO4 in the presence of mercury(II), two isomeric ketones, C and D, are produced . Oxidation of A with KMnO4 gives a mixture of acetic acid (CH3COOH) and the tricarboxylic acid E. Propose structures for compounds A-D, and write the reactions.

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Chapter 9.SE, Problem 54AP

Interpretation Introduction

Interpretation:

Hydrocarbon A(C₉H₁₂) absorbs 3 equivalents of H₂ in the presence of Pd/C to yield B(C₉H₁₈). A when treated with aqueous H₂SO₄ in the presence of Hg(II) gives two isomeric ketones C and D. A upon oxidation with KMnO₄ gives a mixture of acetic acid and tricarboxylic acid E. Based on these data, structures for the compounds A-D are to be given and the reactions are to be written.

Concept introduction:

The degree of unsaturation can be calculated by comparing the molecular formula of compound given with that of its parent hydrocarbon. Both alkenes and alkynes yield alkanes by adsorbing H₂ in the presence of Pd catalyst. Alkynes require two equivalents of H₂ while alkenes require one equivalent of H₂ to give alkanes. Internal alkynes will yield a mixture of isomeric ketones when treated with aqueous H₂SO₄ in the presence of mercury (II) if they are symmetrically substituted. When oxidized with KMnO₄, monosubstituted carbons in both double and triple bonds get oxidized to carboxylic acids.

To give:

Based on the data given, the structures of A-D and to write the reactions.

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