Exam 1 - Chemistry 30B, Winter 2004: Organic Reactions and Mechanisms, Exams of Organic Chemistry

Download Exam 1 - Chemistry 30B, Winter 2004: Organic Reactions and Mechanisms and more Exams Organic Chemistry in PDF only on Docsity! Chemistry 30B Winter 2004 Exam 1 Page 1 1. (9 points) Write the organic product(s) in the boxes. If more than one organic product is formed, indicate which product is major. If no reaction occurs, write “NR.” Do not include any mechanism details. Product(s) (a) OH OH excess CrO3 aq. H2SO4 (b) CH3CO3H (c) OH NaH 2. (12 points) Describe (in one sentence or less) or give a clear example for each term. (a) Alkoxide: (b) Williamson ether synthesis: (c) Oxonium ion: (d) PCC: Chemistry 30B Winter 2004 Exam 1 Page 2 3. (8 points) Provide a complete mechanism for this reaction. OH HgOAc Hg(CH3CO2)2 H2O Questions 4 – 7 refer to the conversion of an alcohol into a toluenesulfonate, a very useful strategy to convert an alcohol into a wide range of other functional groups. 4. (1 point) Write the reactants that are used to convert CH3OH into CH3OTs above the arrow. CH3OH CH3OTs 5. (2 points) Write the complete structure for CH3OTs (no abbreviations) in the box. CH3OTs = 6. (3 points) In one sentence or less finish this statement: OTs is a very good leaving group because..... 7. (3 points) Illustrate the utility of CH3OTs by writing its reaction with a strong nucleophile of your choice. Include all reactants and products but do not include a mechanism. CH3OTs Chemistry 30B Winter 2004 Exam 1 Page 5 18. (10 points) Suggest a series of reactions to carry out the following transformation. You may use any needed reagents and reasonable reactions. Logical retrosynthesis may earn some partial credit, but is not required. This transformation cannot be accomplished in a single step. Iinto Chemistry 30B Winter 2004 Exam 1 Page 6 19. (14 points) Suggest a series of reactions to carry out the following transformation. You may use any needed reagents and reasonable reactions. Logical retrosynthesis may earn some partial credit, but is not required. This transformation cannot be accomplished in a single step. Br HO into CH3O OCH3 OCH3