Question

4. Give reaction conditions for the following reactions. Under each arrow label SN1 or SN2. Lai < 5. Draw the mechanism for each of the reactions in problem 4.

Answer 1

4Theiven neachiorv is H SNL Fin Sat caction initially a fenmatin of Carbocatin dccwes in the mete limiting depaften the eliminatio of the laving ep Chor-OH is ha eaving pfolleedbyafa limtim nuclesphilic attack on hs Carboctio Cen occes Dus to the genenotion of Combocotianic intermediode in the oote delermining in pele highly pelare svart tike auc thandf non norte slocsast hep, Sneactionic fveurole ic a bad leaving gmoups cde nud a dnoul Cauily protonaded and 2 Con be elirinedkd Since, here -6H polae protic Saverton slightly acilic mesiunv Sothat -OH roup as a Cam otentiad leaving opmcup Mechanism of Stneaation Patha OH dilute Hei 1st step: H Protoretin T-s'L Honestable 3-Carbocation Caebocatin laast Stabe Decaengemt H Anans fer

dil Hc fast Nucleophilic attack by e® in em eually orobakle uppen locdenfe of ha planarr g2 Carrbocation ade> k o m Sneaction , it is a onstep Cancented procues whore a backsid nuckophilicc attaak occerrs ana Conbory atom Confeining 1he leoring qroup. Ths Primarcy Carbory atorv,duto lese emc hindnenae Profens to cundengo nueleophilic Suboitetonw via Saf Fon eaction e need a meuch poesen.ful ncleopkil So that Can eaoil attack on the desies Cacbon Contre As in Cur Ca the nucleophilkex Same CAlonide Ce) So cdeshould use a polar aprotic non-protic sofvet. I, thic csaytheefive rudeophile is no Longern curslong H-bnling ulh l ponticend and fecdlive nsckephlitie atlechpsabe DMP(dwt) Nae! OH

Hechanism S- COH HO H H Transitin state Fors Scaction invenciony ccceses in the eaction Centhe Teacte of tha meacttor k[0H][u1