Chem 237 HW Ch. 6: Mechanisms & Products of 2-deuterio-1,3-dimethylcyclopentene Reactions, Assignments of Organic Chemistry

Download Chem 237 HW Ch. 6: Mechanisms & Products of 2-deuterio-1,3-dimethylcyclopentene Reactions and more Assignments Organic Chemistry in PDF only on Docsity! Chem 237, Summer 2008 Homework Ch. 6 Due: 8/1/08 Name: __________________________________________ Ch. 6: 1, 4, 5, 8, 10!, 12, 16, 17, 20, 23, 26, 27, 30, 31, 32, 34, 36!, 37, 38, 39, 41, 43, 47, 48, 49, 50, 51, 56, 57, 58, 59 1. For each reagent (or sequence of reagents), draw the complete mechanism of the reaction with 2-deuterio-1,3-dimethylcyclopentene (except for steps labeled "no mech"), as well as the major product(s) of the reaction. If the reaction can form minor products, draw them and indicate they are minor. Because the reactant is both cyclic and non-symmetrical (one end is less substituted than the other), you should definitely show both the specific regiochemistry (Markovnikov or anti-Markovnikov) and stereochemistry (syn or anti, or a mixture of both) in the product(s). Be careful with stereochemistry! Both "syn" products are not the same, because of the wedged – CH3 on carbon 3 – same thing with the two "anti" products. They may be expected to form in roughly equal amounts, or one may be more likely than the other – use your judgment, based on the mechanism! Of course, before you can make that judgment call, you need to be able to draw the mechanism correctly, so (obviously) start with that first. You absolutely must be able to draw these mechanisms without referring to your notes or the book, so now is your chance to prove to yourself that you can! You will very likely be asked to draw the product(s) and mechanism of one (or more) of these reactions on the final, as well as to reason (not just regurguitate!), based on the mechanism, why a certain stereochemical or regiochemical outcome is observed. CH3 D H3C (a) H2, Pt catalyst (no mech) (b) HCl (c) HBr, peroxides (d) H+, H2O (say, 50% H2SO4 in H2O) (e) 1. B2H6, diglyme (draw mech) 2. H2O2, HO- (don't worry about the mech for the second step, but you should know how/whether it affects the stereochemical outcome of the overall reaction) (f) Br2, CCl4 solvent (g) Br2, H2O solvent (h) 1. O3; 2. Zn, H2O (no mech, either step) (i) 1. Hg(OAc)2, H2O (draw mech) 2. NaBH4, HO- (again, no mechanism, but you should know how it affects the stereochemical outcome) Part (i) is not in the book (regrettably!). If I run out of time, I may have to "unassign" this part. Don't count on it!, but don't worry about it until I'm able to cover it in class.