Fall 2018 Chem 12A Biology Reaction or Industrial Reaction Application This assignment is worth 2 credits. You will work in a group of 2 to 4 to apply 2 or more Course Objectives (except Objective 16) to a Biology reaction or Industrial reaction. The number of group members = number of Course Objectives in your Biology reaction or Industrial reaction. You and your group will give a 5 minute presentation of your Biology reaction or Industrial reaction to the class on the Final Exam date. Each person should present one Course Objective. Your Biology or Industrial Reaction must be a reaction type we have covered in Chem 12A this semester. For your reaction, discuss the reaction type, structural features/reactive sites, mechanism (including curved arrows), and other concepts (functional groups, formal charge, chirality, configuration). Your presentation could be a Powerpoint presentation or you could use Alchemie Animator to show the mechanism. Draw your own structures and reactions by hand or with a chemical drawing software, e.g., ChemDoodle. Do not copy a structure or reaction from a reference source. Do not plan to write your reaction on the board; it will take too long to write! Grading: 2 credits 1.7 credits for presentation content (12A reaction, structural features, mechanism, curved arrows, other concepts (functional groups, formal charge, chirality, configuration) Submit or share your presentation slides with me. 0.3 credits for your evaluation of Chem 12A students learned. 1. identify what you want the Chem 12A students to learn from your presentation. 2. Give the students an assignment that should take 3-5 minutes to complete. Collect this assignment and grade it with a letter grade (A, B, C, D, or F). 3. On a piece of paper, submit this information to your instructor: a. your list of questions from your assignment. b. Summary of the assignment results (number of students and average grade). c. Conclusion: Did the Chem 12A students learn anything from your presentation? Some Possible Biology and Industrial Reactions Substitution reactions 1. Adrenaline: 2. Reverse transcription is the process that generates complementary DNA from an RNA template. It is an essential process by which retroviruses, such as HIV, replicate.
AZT is a drug that inhibits reverse transcription. The OH group is replaced with azide group. Azide group is not nucleophilic and will not undergo substitution at P. 3. Methionine is the most common eukaryote start codon in process of translation of mrna to protein. 4. Chemical warfare and substitution reactions S N 2 reaction:
5. Nitrogen mustard (analog of sulfur mustard) used as cancer treatment. Nitrogen mustard derivatives, e.g., chlorambucil, melphalan, estramustine, uramustine, are anti-cancer drugs, which reacts with DNA leading to death of cancer cells but with undesirable side effects. 6. Terpene synthesis, e.g., dimethylallylpyrophosphate is used as a building block to form GPP. 7. GPP --> FPP --> squalene --> lanosterol
Elimination reactions 8. Fatty acids palmitic acid (sat d) and oleic acid (unsat d). Nature makes them from common intermediates. Fatty acid biosynthesis β-hydroxy butyryl-acp - elimination --> crotonyl-acp reduction --> -->--> fatty acids Omega-3 and omega-6 fatty acids Omega-3 and omega-6 fatty acids common sources: 9. Woodward s 1952 synthesis of cholesterol involved an elimination reaction:
10. Fluorouracil anti-cancer drug. Mechanism of action is an elimination reaction. How a cancer cell divides: thymidylate synthase converts deoxyuridinemonophosphate (dump) to deoxythymidinemonophosphate (dtmp). One step is an elimination reaction. Fluorouracil is an anti-cancer drug (breast, skin, stomach, pancreatic, colon cancers). How does fluorouracil work? Replace H by F and no elimination reaction. Addition reaction 11. Kreb s cycle: how would you classify Step 3? (anti-markovnikov addition)
12. Kreb s cycle Steps 6-8: Beautiful Mind movie: dehydration prevents the Kreb s cycle from functioning effectively after a night-out (hangover).
13. Anti-depressants Synthesis of L-dopa (a precursor to adrenaline): 14. Sudafed contains pseudoephedrine
methamphetamine enantiomer is levomethamphetamine, which is a vasoconstrictor and helps alleviate nasal congestion. Levomethamphetamine is found in vapor inhalers. Industrial reactions Plastics polymerization 15. Cationic polymerization: styrene ---> polystryene (styrofoam). See Klein, Organic Chemistry textbook, p. 405 16. Radical polymerization: e.g., ethylene ---> polyethylene propylene ---> polypropylene 17. vinyl chloride ---> polyvinylchloride (PVC plastic) 18. ethylene ---> tetrachloroethane (perchloroethane, PERC) used in dry cleaning fabrics