1. There is one compound (that contains only one carbonyl group) that gives both a positive iodoform test and a positive Tollens’ test. This compound is not included in the table of unknowns. Use your knowledge of the test to predict this compound and draw it. Hint: the molecular weight of the compound is less than 60

Organic Chemistry
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ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Section10.7: The Pinacol Rearrangement
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1. There is one compound (that contains only one carbonyl group) that gives both a positive iodoform test and a positive Tollens’ test. This compound is not included in the table of unknowns. Use your knowledge of the test to predict this compound and draw it. Hint: the molecular weight of the compound is less than 60

2. Draw the structure of a molecule, an unknown aldehyde or ketone listed in the tables, that would show a negative Tollens’ test and a negative iodoform test. There is more than one correct answer. Draw one!

3. You acquired the following data: bp 173 °C; – Tollens’, + iodoform tests; semicarbazone mp 105 °C. You are very confident that your unknown is 2- octanone. Data is spot on, excluding the semicarbazone mp. You suspect the suppressed mp is due to wet crystals. What process or technique (other than continued oven drying) can help you obtain more pure semicarbazone and thus a more accurate mp for comparison? Please write answer in box at right.

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