Problem_Set_2

Problem_Set_2 - 6. Rank the four ketones shown below in...

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Organic Chemistry c3046y Problem Set 2 - Carbonyls II Relevant Book Problems (Chap. 17): 46, 50, 51, 53(a,b,c,d,f,g), 56, 58, 63, 64(a,d), 65, 68, 69, 73, 75, 82, 84b. Relevant Reading: Chapter 17 (except 17.12, 17.14, and anything to do with "Enamines"). N CH 3 H 3 O + Ph CH 3 OH O H + O Ph CH 3 O O H 2 NCH 3 2. Write out a mechanism for, and predict the product of the following reaction. (It is significant that the starting material is being treated with acid, but not aqueous acid. ..): 3. Write out a mechanism for the following transformation: Hint: You must decide what will happen first with this combination of reagents. This problem illustrates that there are different ways to make acetals. + 1. As we said in class, imine formation is reversible, and the reverse reaction is driven by using an excess of water as well as acid. Write a mechanism for the following transformation + O O Me Me HO H +
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O R O O O H Me O MeO MeO O 2 N Me O A B O Me C Me O Me Me Me D Me O MeO 5. Write out a mechanism for, and predict the product of the following Baeyer-Villiger oxidation:
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Unformatted text preview: 6. Rank the four ketones shown below in order of increasing C=O stretching frequency in the IR spectra. ? 7. Propose a synthesis to accomplish the following transformation: page 2 4. Acetals and Ketals have relevance beyond simple protecting groups. Exo-brevicomin is a naturally- occuring ketal that is a constituent of the pheremone system of bark beetles. Propose a synthesis of exo-brevicomin starting from the illustrated starting material. ( It will be helpful here to work backwards from the product - what is the product? From what components are such things made? If you can make this retrosynthetic disconnection, then the connection between the starting material and your target will be more obvious. Once you see the pathway in broad terms you will then have to figure out how to orchestrate the reactions you need to do. ) ? O O Et Me exo-Brevicomin OH Et OH...
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Problem_Set_2 - 6. Rank the four ketones shown below in...

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