Due: Sunday, February 11, 3PM Show work for all calculations to receive full credit. Synthesis of propranolol (beta blocker medication) 20 g KOH OH C EtOH:H₂O 325 g 1-naphthol epichlorohydrin 50 g intermediate 42 g 185 g 1-Napthol (50g) + epichlorohydrin (185g) -> intermediate (42g) -> propranolol (30g) Catalyst/Reagent 1= KOH (20g) and EtOH.H2O (325g) Catalyst/Reagent 2- MeOH (320g) and C2H8N(400g) METRICS 1. What byproduct is not shown? 2. Define each of the following: 400 g H₂N a. Limiting Reagent b. Percent Yield c. Atom Economy d. Reaction Mass Efficiency e. E Factor 3. For each step, calculate: a. Limiting Reagent b. Percent Yield 4. For the overall reaction, calculate: a. Percent Yield b. Atom Economy c. Reaction Mass Efficiency d. Complete E Factor MeOH 320 g OH propranolol 30 g 5. Based on these answers, what recommendation(s) would you make to improve this process? BIODEGRADABILITY 1. What is the general formula for the group contribution method? What does each term represent? 2. Identify the molecular fragments for propranolol using Table 1 in Boethling, R.S. et al. 1994 (DOI: 10.1021/es00052a018). 3. Calculate: a. Probability of degradation (linear model), Pbiodeg b. Score of ultimate degradation, BI 4. From these calculations, comment on the probability that propranolol will degrade under typical aerobic conditions, as well as the expected timeframe of degradation. If there is any conflict between these two results, what difference between the BIODEG and survey analysis is most responsible? 5. What aspects of the structure of propranolol are overlooked by this analysis?