Question

using 15% NaI-acetone solution

please indicate the expected ranking quickest to slowest

then answer the following questions

Part A: Structural Effects on Sn 1 Reactivity: Names Structures Expected Ranking Exi n-butyl bromide n-butyl chloride sec-butyl chloride tert-butyl chloride crotyl chloride

Answer 1

Among the 5 alkyl holides crotyl chloride undergoes quickest reaction. It is due to a nesonence stabilization as shown W X L X resonence stabilization - next text-butyl chloride undergoes quickest next to cloty chlorida then secondary butyl chloride. It is due to stability of 3° carbocation more than the 2" Secondary carbocation. X l zºcarbocation. 2 carbocation. The n-butyl blomide undergoes fast reaction compare to n-butyl chloride. It is due to (Bot) bromide ion is agood leaving group compare to a chloride. So SN Reactivity of alkyl halides is cratul chloride teet-baty chloride sec-batyl chloride xn-butyl beomide > n-butyl chlolide e substeatee Reagent Products o clotyl chloride NaI B clotyl Iodide Med sodium Iodode 3 - Iodo-1-batene MI ♡ teet-butylchloride tl teet-baly Iodide. NaI ③ secondsey butyl chloride sec-butyl Iodide. Na I NaI -

substract neagent peoduct n-butyl blomide sodium Codice * [n-butyl Iodide This undergoes SN2 type reaction not SN type reaction n-butyl chloride NaI w butyl Iodide. en This reaction also undergoes through sr mechanism. ud + NaI Aating Mit t + Nace. mechanism step-I Carbocation Generation " slowstep carbocation step-I: Nudlophile substitution mechanism o na 3 talt na I Aatong XI + Nach por joka no KI. manent saling me step. 2 tepi

4 This undergoes through SN mechanism. M B + NOT Aalong, M I + naßto mechanism Bhos @ Vers > A SIMINABIO TO NO "Transition that ? 16 ne +NaI Acelone Mitwacl. mechanism Reb: - MI+ Nacl.