14D_f11_finalA

14D_f11_finalA - Chemistry 14D Fall 2011 Final Part A Page...

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Fall 2011 Final Part A Page 1 Page 1 score = Acyl phosphates such as acetoacetyl phosphate are common intermediates in biochemical reactions involving addition or substitution at a carbonyl group. Questions 1–4 explore the chemistry of these molecules. O P O O O O O Acetoacetyl phosphate 1. (9) If a carbonyl is present at the start of a mechanism step, it reacts in one of three common ways (the carbonyl fates). Name these fates, and illustrate each using acetoacetyl phosphate, HO - , water and H 3 O + as the only reactants in each case . If the fate can proceed more than one way, illustrate only the most likely pathway. Include curved arrows. Name of fate #1: ___________________________ Illustration: O P O O O O O Name of fate #2: ___________________________ Illustration: O P O O O O O Name of fate #3: ___________________________ Illustration: O P O O O O O 2. (9) Acyl phosphates are highly susceptible to nucleophilic attack by water. Write the mechanism and major organic product formed in the following reaction. Draw a box around your major organic product. R
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14D_f11_finalA - Chemistry 14D Fall 2011 Final Part A Page...

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