Question

5. (4 points) Draw the configuration(s) of the substitution product(s) that will be formed from the following reactions. (Hint: decide if the substitution will follow an Snl or Sn2 mechanism first.) CH2CH2CH3 will + NH3 H2C polar, aprotic solvent H.CL Br + CH 0 CH3 + CH,OH CH + CH OH Br

Answer 1

5 CH2 - CH2 CH 411444 ) Cry - CH₂ CH2 CH2 + Nih Polar hynte aprohoc Solvent SN mechanism inversimos con sigurahia take place (1) che strong nuclenphil'e Bochoo nome SNP mechanism, backside attack 6ls nucleophile occuis 4 inversion os consigueab co take place. ome + cuenta + CV-OH - romet / gº substrate coea Knuclcophile Yaremis SN mechanism oh is weak nucleophile and the Substrate is 30 Thee it gives stable Carbocahon & Thus SN² mechanism ome tador Gons Nome N Substrate is gº allcyl bromide and cytok is toeak nucleophile. Thus Seachon Proceeding through SNI mechanism

(6) 4 + 000 — OH + Bro Faster ceecling through snę mechanism C o is stoong nuclerophile and Substrate is 2-ally! boomide Thus reachion Proceeding through sne There sore the concentraham ols nuclerophile increases the rate of reach an increases. The rate of SN² uchon also depend concentration of hucleophile. thus Ceach am goes faster is the sewels concentration ols nuclerphile increases. M B + chai-se M SCty + Bro faster Cly-so is strong nucleophile and Substrate is ľally! beomide - "Thuy Seachca Proceeding though 5N2 Mechanism Thus concentration of nuclenphile increases the reaction goes faster. (e) for t o - dol + Boo The substrate is gº aikyl bcorride and nucliophile is weak in nature. This reacher Proceeding through the SN mechanism. The rate als 5N reachem depend Only on concentration of substrate .le it is unimole Cular reaction. The rate is inclependent on cmcentrahom os nuclerophile. Thus reachem does not goes faster is the comcentral on ob the nucleophile is increase.