A hydrocarbon A, C 9 H 10 , is treated with N-bromosuccinimide to give a single monobromo
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A hydrocarbon A, C9H10, is treated with N-bromosuccinimide to give a single monobromo compound B. When B is dissolved in aqueous acetone it reacts to give two nonisomeric compounds: C and D. Catalytic hydrogenation of D gives back A, and C can be separated into enantiomers. When optically active C is oxidized with CrO3 and pyridine, an optically inactive ketone E is obtained. Vigorous oxidation of A with KMnO4 affords phthalic acid. Propose structures for compounds A through E, and explain your reasoning.
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Compound A has an unsaturation number of 5 Because it ultimately affords phthalic acid it is an orth...View the full answer
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