a) Write a detailed reaction mechanism for the following conversion. 17 marks) ОН но Но. Acetone HCI -ОН ОН ОН b) Consider the following compound 2. ОН ОН но НО. он Compound 2 і. Draw the products obtained when compound 2 is hydrolyzed in the presence of an acid. [3 marks) Propose a detailed reaction mechanism for this hydrolysis of compound 2. (5 marks] ii.
c) Study the following reaction scheme for the preparation of a natural glycoside (compound 7) and answer the questions that follow: он OAe HO HO excess Ac,0 pyridine, oC AcO Aco OH OAC OAC он Compound 3 Compound 1 HB OCH ОАс OAC AcO Aco Aco Aco OA ОАс Compound Compounds Br NaOH, H,0 осн, OH w HO HO OH Compound 2 i. Write a mechanism for the reaction of any one of the hydroxyl groups of compound 3 in the conversion to compound 4. [3 marks] ii. Identify the unknown reagent(s) in the reaction scheme which converts compound 5 to compound 6. 12 marks] ili Propose a detailed reaction mechanism for the conversion of compound 5 to compound 6 and concisely explain the stereochemical outcome. 15 marks!
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