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William Ogilvie

CHM 1321A Mid Term 2 Version B Answers 1. Name the following compounds (6 points): a) F Z-2-methyl-7-fluoronona-1,6-diene E-3,6-dimethylhept-2-ene b) 2. a. Compare the two hydrogens shown in this compound and circle the one that is more acidic. (1 point) H H a. Draw the two possible conjugate bases (2 points). H H b. For your answer above, identify which of the conjugate bases is more stable and briefly justify your answer (4 points) 1 compound on the left resonance is possi1le resonance stabilizes conjugate bases by spreading out the charge 2 3. a. Compare the two nucleophiles shown in this compound and circle the one that is more nucleophilic. (1 point) HS OH b. Justify your answer for part a (4 points) Sulfur is lower in periodic table than O Sulfur is larger than O Electrons in sulfur are held less tightly that in O Sulfur is a better electron donor (nucleophile) than O 4. Consider the following reaction. NH 2 HN + NaOH + NaBr + H 2 Br a) Write a detailedmechanism for this transformation (8 points). 1 1 1 1 H 2 H N 2 NH NH H 1 H O Br OH + 2 1 1 1 S N = -2 N- -1 1 (b) Draw the reaction co-ordinate diagram for the process shown above. Label the starting materials, products, transition state(s) and any intermediate(s). (11 points). 1 transition state 1 transition state shape 1 2 intermediate transition state H N 2 1 intermediate 1 H N Energy H 1 1 NH H2N 1 + NH2CH3 Br Reaction Coordinate 1 5. Write a detailed mechanism for this transformation (13 points). HO OH H2SO4 O C 4H8O2 1 1 1 1 H 1 + O O O -H O HO OH + HO OH H 2 1 1 1 O 1 1 O 1 1 6 membered ring S N1 -2 1 oxygen position O- -2 6. Consider the following reaction: OCH 3 OCH 3 NaOCH 3 C H BrO 16 17 2 a) Draw the starting material for the process and the mechanism of the reaction, neglecting stereochemistry (6 points). 2 1 OCH
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