F10 Chem 226

Exam 1 WorkSheet

For Practice Only

This is not a sample test. It is designed for practice to help you prepare for the exam. There are many learning goals for the exam that are not part of this worksheet.

1a. Identify all of the functional groups in Crixivan shown below.

Crixivan (an HIV protease inhibitor)
N N N HN C(CH3)3 O O OH H N HO

b. Identify all the sp2 atoms in Crixivan. c. Identify all 3 hydrogens. d. Identify all atoms that can hydrogen bond with water as a H-bond donor, receiver or both. 2. The nitronium ion, NO2+, is formed when concentrated nitric and sulfuric acid are mixed. a. Write the Lewis structure including the formal charges. b. State the hybridization and VSPER geometry around nitrogen, and the bond angle between oxygen atoms. c. Draw a 3D picture showing the orbital overlap in this ion. Label all sigma and pi bonds, and identify the types of orbitals that overlap to form these bonds. 3. There are four amides with the formula C3H7NO. a. Write Lewis and line-angle formulas for each structure. b. One of these amides has a melting and a boiling point that are substantially lower than the other three. Which amide? Explain your answer. c. Can you think of any property or techniques that may help you distinguish between any of the other three amides? Speculate, its an open-ended question not from textbook. 4. Draw all resonance forms including formal charges. Use correct arrow notation.
N O

5. Use the product distribution data for the reaction below to calculate the relative rate of reactivity of the 1 and 3 hydrogens in free radical bromination reactions.
Br2 h 92%
Br

+ 8%

Br

F10 Chem 226

Exam 1 WorkSheet

For Practice Only

6. Write the complete reaction mechanism for the reaction shown in 5 above. Show all steps and use the curved arrows to indicate electron movement. 7. Predict the product ratios expected for the following reactions using the reactivity information. Reactivities: For Cl2: 1 1; 2 4.5; 3 5.5. a.
Cl2 h

For Br2: 1 1; 2 82; 3 1,600

b.
Br2 h

c. Would reaction a. above be a good way to make 1-chloro-2,2,4-trimethylpentane? Why or Why not? 8. A chloro group is about the same size as a methyl group; however, dichloroethane is less stable in the eclipsed conformation then butanes eclipse form looking down the C2-C3 bond. Explain why size isnt everything. What destabilizes this dichloroethane conformer? What types of strain are present? Draw Newman projections to support your answer.
Cl

9. Lindane is a pesticide made from the chlorination of benzene in the presence of ultraviolet light. Draw the most stable chair conformation of lindane, also called -hexachlorobenzene.
st nd

Cl Cl Cl Cl

Cl

10 a. Draw a reaction-energy diagram that shows the 1 and 2 propagation steps in the free radical chlorination at a 2 carbon. b. Label the reactants, intermediate, product, transition state, H and EA. c. Identify the rate-limiting step. Does the structure of the transition state look like the reactants or products? How do you know? d. State whether each step in the reaction and the overall reaction is endothermic or exothermic. e. How would this diagram change if the reaction involves the abstraction of a 3 H? f. Repeat 9a-d for bromination at a 3 carbon. g. Free-radical chlorination of 2,3-dimethylbutane gives a mixture of two products, but freeradical bromination of the same alkane gives only one major product. Explain this observation, and include pictures of the relevant energy diagrams in your answer.
Cl Cl Br

Cl2 h

Br2 h >90%

48%

52%