Problem_Set_2 - 1,4-pentadiene (b) Which diene adds the...

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Chem 358 Spring 2007 Problem Set #2 Chapter 15 : 15 .38, 39, 40; Chapter 16 : 16 .3, 4, 6, 8, 9, 10 Additional Problems (1) Predict the major product for the following reactions. Be sure to indicate stereochemistry and, where applicable, draw both enantiomers if the product is chiral. OCH 2 CH 3 O O O O + Heat (a) [From Prelim 1, 2006] O O (b) (2) [From Prelim 1, 2006] Give the diene and the dienophile pair that will lead to the products given. If more than one pair is possible provide the pair that will exhibit the highest reactivity. CO 2 Me CO 2 Me NC EtO 2 C EtO 2 C 3. (a) Draw the structures of the products for the addition of H + to 1,3-pentadiene and 1,4-pentadiene. H + H + 1,3-pentadiene
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Unformatted text preview: 1,4-pentadiene (b) Which diene adds the proton faster? (c) Which one gives the more stable product? 4. Arrange the following carbocations in order of decreasing stability. Draw all the possible resonance forms for each of them. H 2 C CH 2 + H 2 C CH 2 + H 3 C CH 3 + H 2 C CH 2 + 5. Cyclooctatetraene A exists in equilibrium with less than 0.05% of a bicyclic isomer B which is trapped by Diels-Alder cycloaddition to maleic anhydride to give compound C. What is the structure of isomer B? O H H O O C B O O A O 6. On the basis of Hckels rule label each of the following as aromatic or antiaromatic. H H...
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