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Unformatted text preview: YHQWV WKLV UHWDUGV UHDFWLRQ UDWH /DUJH QHJDWLYH LRQV DUH OHVV VROYDWHG WKLV VSHHGV XS UHDFWLRQ UDWH FRQWLQXH«  7KH 61 0HFKDQLVP RI 1XFOHRSKLOLF 6XEVWLWXWLRQ 7HUWLDU\ DON\ KDOLGHV DQG 61 PHFKDQLVP" 7HUWLDU\ DON\O KDOLGHV DUH YHU\ XQUHDFWLYH LQ VXEVWLWXWLRQV WKDW SURFHHG E\ WKH 61 PHFKDQLVP 'R WKH\ XQGHUJR QXFOHRSKLOLF VXEVWLWXWLRQ DW DOO" <HV %XW E\ D PHFKDQLVP GLIIHUHQW IURP 6 1 7KH PRVW FRPPRQ H[DPSOHV DUH VHHQ LQ VROYRO\VLV UHDFWLRQV FRQWLQXH«  7KH 61 0HFKDQLVP RI 1XFOHRSKLOLF 6XEVWLWXWLRQ FRQW +\GURO\VLV RI WHUWEXW\O EURPLGH &+ &+ & +  %U   &+  2 &+ & &+  2+   +  2 + &+ + &+ + & + &+ &+  %U    ±  %U  FRQWLQXH«  The SN1 Mechanism of Nucleophilic Substitution (cont) Hydrolysis of tert-butyl bromide (cont): CH3 CH3 C H .. Br: .. + CH3 : O: CH3 H + O: C H Rate = k[(CH3)3CBr] The mechanism of this step is not SN2 It is called SN1 and begins with ionization of (CH3)3CBr H CH3 The reaction rate is independent of the concentration of the nucleophile and follows a first-order rate law This is the nucleophilic substitution stage of the reaction CH3 + .. – : Br: .. 6WHUHRFKHPLVWU\ RI DQ 61 5HDFWLRQ &+ 5 ± %URPRRFWDQH + & %U FRQWLQXH« &+ &+  + +2 &+ & &+ &+ 6   2FWDQRO  &+ +2 + & 2+ &+ &+  5  ± 2FWDQRO   0HFKDQLVP 6XPPDU\ 61 DQG 61 5HDFWLRQV 3ULPDU\ DON\O KDOLGHV XQGHUJR QXFOHRSKLOLF VXEVWLWXWLRQ WKH\ DOZD\V UHDFW E\ WKH 61 PHFKDQLVP 7HUWLDU\ DON\O KDOLGHV XQGHUJR QXFOHRSKLOLF VXEVWLWXWLRQ WKH\ DOZD\V UHDFW E\ WKH 61 PHFKDQLVP 6HFRQGDU\ DON\O KDOLGHV XQGHUJR QXFOHRSKLOLF VXEVWLWXWLRQ WKH\ UHDFW E\ WKH 61 PHFKDQLVP RFFXUV LQ WKH SUHVHQFH RI D ZHDN QXFOHRSKLOH VROYRO\VLV 61 PHFKDQLVP RFFXUV LQ WKH SUHVHQFH RI D JRRG QXFOHRSKLOH FRQWLQXH«  6XEVWLWXWLRQ YV (OLPLQDWLRQ &RPSHWLQJ 5HDFWLRQV 7ZR 5HDFWLRQ 7\SHV $ON\O KDOLGHV FDQ UHDFW ZLWK /HZLV EDVHV E\ QXFOHRSKLOLF VXEVWLWXWLRQ DQGRU HOLPLQDWLRQ βHOLPLQDWLRQ ± & + + & <  ; ± & &  < + ; ± & FRQWLQXH« &  ; < QXFOHRSKLOLF VXEVWLWXWLRQ  6XEVWLWXWLR...
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