Chemistry 1027A/B Lecture Notes - Lecture 23: Protic Solvent, Steric Effects, Alkane Stereochemistry

• School: Western University
• Department: Chemistry
• Course: Chemistry 1027A/B
• Professor: Mark Workentin

Document Summary

Sn1 and e1 have identical rate determining steps, so they generally occur simultaneously and have the same properties. Sn2 and e2 one step this single step is the rate-determining step (rds) Sn2: steric hindrance blocking nu (nu is in rds) E2: blocking b isn"t a big obstacle (b doesn"t join substrate) Sn2: inversion (backside attack, since lg blocks frontside) E2: cis vs. trans determined by anti-periplanar transition-state. E2: possible products from deprotonation of any -carbon major product w/ bulky base: less substituted (steric hindrance) major product with non-bulky base: more substituted. Sn2: methyl>1 >2 ; 3 gives no sn2 (substitutents block nu) E2: 1 , 2 , or 3 (blocking b is not a big obstacle) Sn1/e1 two steps rds is formation of carbocation stabilizing carbocation (nu/b isn"t in rds, so blocking it isn"t an obstacle) E1: both cis and trans isomers will be produced.