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Supplement_to_PS__7___solutions - This condition is mild...

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Supplement to Problem Set 7 – solutions Comments on question 3: Product B: Ozonolysis work up to give aldehydes is usually achieved by using either (a) dimethyl sulfide (DMS) (textbook pages 173-175) (preferred when acid-sensitive groups are present in the molecule) or (b) Zn/H 2 O (can also be used in the presence of acetals). For the workup using Zn/H 2 O, a small amount of acid (usually acetic acid) is added and the reaction is just stirred at room temperature.
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Unformatted text preview: This condition is mild enough that it does not remove acetal protecting groups. So product B retains the acetal group. In the sequence of reactions shown below (from question 3) you may replace Zn/H 3 O + with Zn/DMS. The actual reaction was performed in practice as originally shown in question #3. O O 1. O 3 , CH 2 Cl 2 2. Zn/H 3 O + 3. Ag 2 O THF-H 2 O C 9 H 14 O 4 B O O CO 2 H B =...
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