Midterm 1 (100 pts) Chem 2211 By submitting my work online for this midterm, I declare that I have received no outside help and have abided by all academic honesty policies of Florida State University. Section I. Tactics (42 pts) Provide the appropriate reagents, starting material, or product in the following examples. 1. I Me Me Me 2. 1. AcCl, AlCl3 2. Li, NH3, tBuOH 3. MeMgBr, THF 3. O 1. PhMgBr, THF 2. PCC, CH2Cl2 3. Me , 100 °C 4. O OMe OMe Me Me OH 5. N H 2N N 6. OH 1. K2Cr2O7, H2SO4, H2O 2. NaH, CH3I, DMF 3. NaBH4, MeOH HO 7. Br Me OH Me Section II. Structure and Mechanism (30 pts) 1. a. Borole is a particularly unique heterocycle that has gained considerable attention in recent years for its peculiar reactivity. Draw a molecular orbital diagram for the pi system of borole (including the placement of its pi electrons) and provide an analysis of its aromaticity using Hückel’s rule denoting whether borole is in fact aromatic, antiaromatic, or nonaromatic. H B Borole b. Provide a picture of the Highest occupied Molecular Orbital (HOMO) and the Lowest Unnocupied Molecular Orbital (LUMO) of borole depicting the phases of the p orbitals, the bonding, antibonding, and non-bonding interactions. 2. a. The following intermediate was important in teh synthesis of a steroid derivative that had shown promising anticancer activity. For the numbered carbons, determine their oxidation level. Me 3 N 1 2 Me Me b. When treated with bromine, the compound undergoes a reaction to form a tricyclic product. Provide a detailed reaction mechanism for the following transformation. Me N CH2Cl2 Me Me Me Br2 N Br H Me Me c. Provide a brief synthesis of the deisired intermediate A from the given starting material and fragments with 4 carbons or fewer. Me Me O Me H N Br Me A starting material 3. The utilization of diols as intermdiates towards the ultimate oxidative cleavage of alkenes is an important process. Provide the predicted structure of A and then the structure of B with a mehcanism of its formation. product A (R = H) strong and broad IR absorption at 3300 cm-1 EtMgBr (1 equivalent) R O THF; then HCl EtMgBr (1 equivalent) THF, rt Cl mechanism? product B (R = NO2) no IR absorption at 3300 cm-1 Section III. Strategies – Total Synthesis (28 points) Biphysovenisole is a recently isolated natural product that shows promising neuroregenerative properties. Propose a synthesis of Biphysovenisole starting from the given starting materials and carbon fragments of three or fewer. You are not required to show a retrosynthesis, but showing one can get you partial credit if you do not show a forward synthesis. H O MeN O O N H Me Biphysovenisole Me N Me N-methylindole
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