Chem238StoryPractice - 3 and a third compound B with the...

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Chem. 238 Practice Story Problems 1. Myrcene, a fragrant compound found in bayberry was, has the formula C 10 H 16 and is known not to contain any triple bonds. When treated with excess hydrogen and a platinum catalyst, myrcene is converted to compound A with the formula C 10 H 22 . How many rings does myrcene contain? How many double bonds? Compound A can be identified as 2,6-dimethyloctane. Ozonolysis of myrcene followed by treatment with zinc and acetic acid yields 2 mol of formaldehyde (HCOH), I mol of acetone(CH 3 COCH
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Unformatted text preview: 3 ), and a third compound B with the formula C 5 H 6 O 3 . What is the structure of myrcene? What is the structure of B ? 2. Compound A, which is degradation product of an antibiotic has the following structure: CH 3 COCHCHCH 2 CH 2 COCHCHCOOCH 3 The structure was confirmed by converting A to compound B, C 11 H 18 O 4 , which was also prepared by ozonolysis of compound C, C 11 H 18 O 2 . Assign structures to compounds B and C. A B H 2 Pd/C O 3 C 11 H 14 O 4 C 11 H 18 O 4 C 11 H 18 O 2 C...
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