Chem 2320 Quiz 2

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) What is(are) the expected product(s) of the following reaction? Include the structure(s) as a part of your answer.
   
2. (5 pts) What is the relationship between the structures shown below?
   
   Are they diasteroemers, constitutional isomers, resonance forms, or different conformations of the same compound? Justify your answer for full credit.
3. (5 pts) How many resonance forms exist for the carbocation formed by the S_N1 ionization of 4-bromo-2,5-heptadiene? Show the structure of each resonance form, if any do in fact exist.
4. (5 pts) Methanolysis of 4-bromo-2-methyl-2-pentene results in the formation of a major and a minor product. Draw the reaction pathway, showing the structures of the reactant, the carbocation intermediate, and the products. Correctly label the products as major and minor.
5. (5 pts) Which one of the following compounds gives only a single allylic bromide on heating with NBS in carbon tetrachloride? Justify your answer for full credit.