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quizzes_Quiz_4 - 3 O(c H 3 C CH 3 COOH 3 Physostigmine is...

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Chem239A Summer, 2007 Quiz#4 Prof. Sasaki ______________________________________________________________________ 1. Describe procedures for preparing each of the following compounds, using ethanol as the source of all their carbon atoms. Once you prepare a compound, you need not repeat its synthesis in a subsequent part of this problem. (a) Ethylamine (d) N,N-diethylacetamide (b) N-Ethylacetamide (e) Triethylamine (c) Diethylamine (f) Tetraethylammonium bromide 2. Starting from n-butyl bromide (CH 3 CH 2 CH 2 CH 2 -Br), outline a synthesis for the following compounds. You may use any reagents that you wish. (a) (b) H 3 C COOH H 3 C CH 3
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Unformatted text preview: 3 O (c) H 3 C CH 3 COOH 3. Physostigmine is an alkaloid obtained from a western African plant; it is used in the treatment of glaucoma. Treatment of physostigmine with methyl iodide gives a quaternary ammonium salt. What is the structure of this salt? N N CH 3 CH 3 OCNHCH 3 O physostigmine 4. When the compound shown below was heated in refluxing hydrochloric acid for 60 hours, a product with the molecular formula C 5 H 6 O 3 was isolated in 97 percent yield. Identify this product. Along with this product, three other carbon-containing substances are formed. What are they? CH 3 O CH 3 O O O OCH(CH 3 ) 2 OCH(CH 3)2...
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