Question

10) Write out the following reactions giving the major organic products, showing the proper regiochemistry and stereochemistry where needed. Give a complete electron (arrow) pushing mechanism under the reactions where asked to do so. Label all appropriate mechanisms as SN1, SN2, El or E2 a. trans-2-methylcyclopentanol with HCI. (Give a mechanism) b. trans-1-bromo-2-methylcyclopentane with a methanolic solution of AgNOs. c. iodoethane with sodium cyanide (Na CN). d. 1,2-dimethylcyclobutanol with concentrated sulfuric acid at 95 C (Give a mechanism) e. S-2-bromopentane with Nal in acetone f. 2-bromo-3-methylhexane with KOtBu (Give a mechanism) Write out and organize you answers and hand them in BY NOON FRI. FEB. 1 and receive extra credit (E Electronically prepare your answers and upload them in the EC1 site for extra extra credit.

Answer 1

(A) Trans-2-newypegelopenhanof with mei 0 H Me Me (more stable a. Me M2 el (A) 50Y. o Me (O 50% > greater leaving group in natune MeOH Me cis-plcdud) (Product) SN2. path (mtesmeduiate) dl M2 Canc. H,54 Me Me SN 7-OH Me outcud ManaN MW (Mino)