A contains only carbon and hydrogen. Upon treatment with acidic water in the presence of mercury (II) sulfate, a single product B, is obtaioned. A reacts with hydrogen and Lindlar's catalyst to give C, which reacts with acidic water to give D and essentially nothing else. D reacts with concentrated sulfuric acid to give almost entirely E and not C. E reacts with ozone followed by zinc in water to give ketone F and aldehyde G. E reacts with acidic water to give almost exclusively H and not D. H reacts with dilute sulfuric acid to give a mixture of E and I. I reacts with ozone followed by zinc to give J, a single molecule that is both an aldehyde and a ketone. Identify A-J, there is a compound for each letter in that series. Note that there is not one completely unique answer as you can add more complexity than necessary, but all will share important features. Assume no rearrangements and normal reaction conditions. Draw the structures and each transformation as a reaction.

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2. A contains only carbon and hydrogen. Upon treatment with acidic water in the presence of mercury (II) sulfate,
a single product B, is obtaioned. A reacts with hydrogen and Lindlar's catalyst to give C, which reacts with acidic
water to give Dand essentially nothing else. D reacts with concentrated sulfuric acid to give almost entirely E
and not C. E reacts with ozone followed by zinc in water to give ketone F and aldehyde G. E reacts with acidic
water to give almost exclusively H and not D. H reacts with dilute sulfuric acid to give a mixture of E and I. I
reacts with ozone followed by zinc to give J, a single molecule that is both an aldehyde and a ketone.
Identify A-J, there is a compound for each letter in that series. Note that there is not one completely unique
answer as you can add more complexity than necessary, but all will share important features. Assume no
rearrangements and normal reaction conditions. Draw the structures and each transformation as a reaction.
Transcribed Image Text:2. A contains only carbon and hydrogen. Upon treatment with acidic water in the presence of mercury (II) sulfate, a single product B, is obtaioned. A reacts with hydrogen and Lindlar's catalyst to give C, which reacts with acidic water to give Dand essentially nothing else. D reacts with concentrated sulfuric acid to give almost entirely E and not C. E reacts with ozone followed by zinc in water to give ketone F and aldehyde G. E reacts with acidic water to give almost exclusively H and not D. H reacts with dilute sulfuric acid to give a mixture of E and I. I reacts with ozone followed by zinc to give J, a single molecule that is both an aldehyde and a ketone. Identify A-J, there is a compound for each letter in that series. Note that there is not one completely unique answer as you can add more complexity than necessary, but all will share important features. Assume no rearrangements and normal reaction conditions. Draw the structures and each transformation as a reaction.
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