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Practice%20EXAM%203 - Dr.Malgorzata Deyrup All rights...

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Dr.Malgorzata Deyrup. All rights reserved. Copyright: Department of Chemistry University of Florida PRACTICE EXAM 3 CHM 2211-0787-Fall 2009 Name: _________________________________ UF ID# :___________________ (PRINT LAST NAME 1. (36) Write product(s) of the following reactions: a. b. c. CO 2 Et CO 2 Et + Br 2 NaOEt 1. H + /H 2 O 2. heat H 3 C H 3 C O O CH 3 1. LDA 2. PhCHO 3. H + /H 2 O Br O H + O H HO - d. e. O O 1. HO - 2. H + CO 2 Et Me CO 2 Et NaOEt EtOH 2. (24) Show the mechanism for the reactions below: O O + EtO 2 C O CO 2 Et NaOEt OH CO 2 Et EtO 2 C Ph Ph 1
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3. (28) Starting with ethyl p-methoxybenzoate propose a reasonable synthesis for the following acetal. You can use any reagents you need and up to 4 carbon compounds in your synthesis. The process has to include some type of condensation. Work back retrosynthetically. CO 2 Et O O MeO OMe 4. (28) Design synthesis starting with ethyl benzoate and any reagent that provides no more than 7 carbons to the final product. O OMe Ph Ph 5. (20) Show mechanism and the product for the following reaction: O O + O NaOEt/EtOH 6. (20) Propose reasonable mechanism for the following transformation. Although you have to show the mechanism forward you may find it helpful to start it from the back part way to the middle. (Don’t be afraid of
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