Review problems #1 - the reaction conditions. (Dont worry...

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September 20, 2007 Review Session Problems 1. Put the following carbonyl compounds in order of decreasing reactivity towards a nucleophile. Justify your ordering. O OH O OMe O Cl O H O O O - 2. What reagents and conditions would you use to carry out the following transformation? What is the name for this type of reaction? O ? 3. Draw mechanisms for the following 3-step reaction. (Hint: Use an acetal protecting group) H O O 3 steps H OH O 4. Draw mechanisms by which molecule 1 converts to intermediate 2 using: a) aqueous HCl b) aqueous NaOH O 1 HO OH 2 5. What product will be formed in the following reaction? O 1) EtONa/EtOH 2) O 3) HCl/H 2 O 6. How would you make the following product by an Aldol condensation without forming any other products? Specify the reagents that you would use, as well as
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Unformatted text preview: the reaction conditions. (Dont worry about E,Z-isomerism) H O 7. Draw the mechanism and the product of the reaction between enolate 1 and , -unsaturated ketone 2, followed by a workup in aqueous HCl. (Hint: product is an acyclic diketone). What is the name for this general type of reaction? O-1 + O 2 8. In basic conditions, the product shown in Question 7 would react with itself to form a cyclic product. How many different products could be formed by this intramolecular reaction? What are they? Which would you predict to be major products, which would be minor products, and why? Stay tuned for solutions to these problems, to be posted on bSpace on Tuesday, September 25....
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This note was uploaded on 07/15/2008 for the course CHEM 3b taught by Professor Pederson during the Fall '08 term at University of California, Berkeley.

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Review problems #1 - the reaction conditions. (Dont worry...

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