Chem 2320 Quiz 3

Instructions: This quiz is open-book. You may use any book, magazine, or other printed or web-based materials you feel are helpful. You may discuss this quiz with other members of this immediate class and section. I will award extra credit (5 pts) to those who work in groups of 2-5 and who submit a group quiz. You may not consult with anyone outside of this immediate class and section about this quiz. You must show all your work for full credit, or to receive partial credit if you make a mistake.

1. (5 pts) Consider the compounds 2,3-diethyl-1,3-butadiene, 3,4-dimethyl-1,5-hexadiene, 2-ethyl-3-methyl-1,4-pentadiene, and 3,4-dimethyl-2,5-hexadiene. Which one of the compounds undergoes 1,4-addition with bromine? Explain why, and why the others do not. Show the entire reaction pathway.
2. (5 pts) For the reaction of 1,3-butadiene with hydrogen bromide at -80°C, draw the structure and give the name of the kinetically controlled product. What are the structure and name of the minor product in this reaction at this same temperature?
3. (5 pts) When 1,6,8-nonatrien-3-one is heated an intramolecular Diels-Alder reaction takes place. Draw the structure of the major product.
4. (5 pts) In the reaction of 2-methyl-1,3-butadiene with what product is formed?
5. (5 pts) Give the structures of the diene and dienophile needed to synthesize the following molecule: