HT3-302X-07 - Hour Examination#3 Chemistry 302X 2007 We...

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Hour Examination #3, Chemistry 302X - 2007 “We must never stop lernig.” Hilary Lincoln Jones 1 (24 points). Here is a lovely problem encountered some time ago, by your old buddy, Amy Alonza Stagg. Your overall job is to write a mechanism for this change. CH 2 O NaOH/H 2 O HO O 1 Here is what Amy thought: She ventured the (correct) opinion that compound 2 was the key intermediate. So, all you have to do is find a way to convert 2 into 1 , and to form 2 from starting material, and the problem is solved. Here is how Amy made 2 from starting material: CH 2 O CH 3 O HO HO 2 add hydroxide as shown, then protonate with water Here are your tasks: (a) Explain to us why Amy s mechanism for forming 2 is hopelessly wrong. (b) Write a mechanism for transforming 2 into 1 in base. (c) Write a better mechanism than Amy s for making 2 from starting material.
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2 (22 points). Here are two synthesis questions. Remember what your grandmother told you - going backward is often a good thing.
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