Chem 1120 Quiz 4

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. You may not discuss, receive help on, or work on this quiz with tutors, friends, family members, or any one outside of class without my explicit permission. Violation of this stipulation is academic misconduct and is grounds for dismissal from class. You must work the quiz in its entirety by yourself before meeting in groups to compile a group quiz. I will award extra credit (5 pts) to those who work in groups of 2-5 and who submit a group quiz. You must show all your work for full credit, or to receive partial credit if you make a mistake.

1. (3 pts) Describe the similarities and differences between the carbon atoms, oxygen atom, and nitrogen atom in N,N-diethyl-m-toluamide (DEET). Be sure to include hybridization, geometry, and bonding in your discussion.What sorts of intermolecular bonds might this compound form? Which atoms will be involved?
   
   
   
   
   
   
2. (2 pts) An unknown carbonyl compound reacts with n-propanol in the presence of concentrated sulfuric acid to form 2,2-dipropoxyhexane. What is the unknown compound? Show the reaction, including all steps and all backbone structures of any organic compounds formed during the course of the reaction. Identify the chemical class of all organic compounds involved in the reaction. Point out all changes in hybridization and geometry that occur during the reaction.
3. (3 pts) Show the reaction of 2,4-pentanedione with sodium borohydride, including the structures of all organic compounds involved in the reaction. Show the catalytic hydrogenation of 1-hydroxy-2-butanone, including the structures of all organic compounds involved in the reaction. How are these two reactions similar, and how do they differ?
4. (3 pts) Consider the selective oxidation of (a.) 2-methylpropanal and (b.) 1-hydroxy-2-butanone. Show the reactions for each, including the structures of all organic compounds involved in the reaction. Which requires the greater number of grams of oxygen, the combustion of 25.0 grams of the product of (a.) or the combustion of 25.0 grams of the product of (b.)? How many grams of oxygen are required in each case? Show the calculations used to support your answer.
5. (9 pts, 3 pts each) Show the synthesis of 1,1-dimethylethyl 2,4-dimethylpentanoate using (a.) an acid and an alcohol, (b.) an acyl halide and an alcohol, and (c.) an acid anhydride and an alcohol. Show the names and skeletal structures of all reactants and products in these reactions.