Homework%2013 - Homework 13 Fall 2009 CHM 2211-0787 1....

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Homework 13 Fall 2009 CHM 2211-0787 1. Write the mechanism for the following retro-aldol condensation: O OH O HO - O O O 2. Write mechanism for retro aldol reaction, followed by aldol condensation leading to a different compound: OH O O 3. Propose the mechanism for the following transformation: O HO - 4. Try these simple syntheses: O O + NaOEt O a. O H b. O Me c. OH OH COOH
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5. Propose mechanism for the following: a. O HOOC HO heat 6. Write products of the following reactions: a. b. O CO 2 Et 1. NaOEt 2. 3. H 3 O + /H 2 O/heat Br(CH 2 ) 3 Br COOH COOH O 1. Heat 2. MeMgBr 3.H + /H 2 O 4.H + /heat 7. Write mechanism for the following cyclizations: O O Ph O Ph HO - a. b. EtO 2 C CO 2 Et + EtO - Na + O CO 2 Et c. CHO O HO - O 8. Show the starting materials that were used to give the following ketoesters:
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O CO 2 Me a. O CO 2 Me b. c. O CO 2 Et d. CO 2 Et O e. H O Ph O O f. Ph O O O 9. How can you synthesize 2-benzylcyclohexanone starting from the ethyl 2-oxocyclohexylcarboxylate O O O O 10. Provide the mechanism for the following cyclic keto ester:
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Homework%2013 - Homework 13 Fall 2009 CHM 2211-0787 1....

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