[A MECHANISM FORTHE REACTION _ Mechanism for the Sy2 Reaction | Reaction HO + CH,cl —> CH,OH + cl Transition state Tho nogative hydroxido In the traneition Now the bond jon brings @ pair of state, a bond between the oxrven ‘electrons to the partially between oxygen ‘and carbon has positive carbon from ‘and carbon is formed and the the back side with partially formed chloride ion has respect to the leaving, ‘and the bond departed. The ‘group. The chlorine between carbon configuration of the bogine to move away and chlorine i carbon has inverted. ‘with the pair of partially broken. ‘electrons that ‘The configuration bonded ito ‘of the carbon the carbon. ‘atom begins to invert.[A MECHANISM FORTHE REACTION ~ Mechanism for the Sy1 Reaction ] CH, Gb Ss + oO — on ‘Aided by tho polar solvent, a chlorine departs with the ‘electron pair that bonded ito the carbon. CH OH + HOt + CH fa SP tis mucn cig + 3G Taneiton “aijernan ‘ ~ Slalet AGF oF ‘os Tees ins 8 a ne sonest tap This slow step produces AFoy, ‘ato anda chloride ion. Although not shown here, the tone ate solvate (and Reaction coordina= stabilized) by waterStep 2 ‘Step 3 on, stop 2 fest ae —H === cH-G—OtH rareo ‘cH, Is oH CH, H AG ‘Avrater molecule acting The products a ‘a5 a Lewis base donates —_tort-butyloxonium ion ‘an electron pair to the (or protonated = carbocation (a Lewis acid). __ tert-butyl alcohol). The shen she cette ateono. eacton coordinate carbon eight electrons. Hy 1H tN te ont ses cH C—O 6-H BE cH ‘Transition eh | I state 3 CHy H H CH, Hi ‘A.water molecule acting The products are tert-butyl a aBronsted base ‘alcohol and a hydronium is accepts a proton from jon. = — 8 the tert-butyloxonium ion. Reaction coordinate