Problem%20Set%202%2009

Problem%20Set%202%2009 - of HBr. 4. Predict the products of...

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Chem 152 Spring 2009 Problem Set # 2 1. Treatment of 3,4-dibromohexane with strong base leads to loss of 2 equivalents of HBr and formation of a product with the formula C 6 H 10 . Three products are possible. Name each of the three, and tell how you would use 1 Hand 13 C NMR spectroscopy to help identify them. 2. Electrophilic addition of Br 2 to isoprene yields the following product mixture: H 2 C C CH 3 C H CH 2 Br 2 H 2 C C CH 3 CHBrCH 2 Br BrCH 2 C CH 3 C H CH 2 Br BrCH 2 C CH 3 C H CH 2 Br + + (3%) (21%) (76%) Of the 1,2-addition products, explain why 3,4-dibromo-3-methyl-1-butene (21%) predominates over 3,4-dibromo-2-methyl-1-butene (3%). 3. Propose a structure for a conjugated diene that gives the same product from both 1,2 and 1,4 addition
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Unformatted text preview: of HBr. 4. Predict the products of the following Diels-Alder reactions: a. CHO + ? b. O O O + ? c. O O ? + 5. How would you use Diels-Alder reactions to prepare the following products? Show the starting diene and dienophile in each case. a. H CN b. O O 6. We've seen that the Diels-Alder cycloaddition reactio is a one-step, pericyclic process that occurs through a cyclic transition state. Propose a mechanism for the following reaction: H 2 C CH 2 + Heat...
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Problem%20Set%202%2009 - of HBr. 4. Predict the products of...

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