8/21/2019 SM-39

1/18

!"##$%&$' %)*"&+),% -). /012&$. 34

56789:; >e >I_^O

8/21/2019 SM-39

6/18

A J$0+(2$,& K.,+.0 ($ .33$/%.,1 @#=.,23 L)'/2&(#1 M'

&%'32*23

8/21/2019 SM-39

7/18

J$0+(2$,& *$# L).%('# HI Y ;'('#/2,2,= #'.3(2$,& /'3).,2&/& D

().( ()' #.('X-'('#/2,2,= &('% /+&( ).5' . 0.#=' %$&2(25' ! 5.0+' ().(

,'.#01 3.,3'0& $+( ()' 0.#=' ,'=.(25' 5.0+' *$# ()' *2#&( &('%9 Z((.37

D,('#%#'(.(2$, $* . 5.#2.(2$, 2, :.//'(( ! 5.0+' 62() .,$()'#

&(#+3(+#.0 5.#2.(2$,9

!"##$%&$' %)*"&+),E)' #'.3(2$, 2& $

8/21/2019 SM-39

8/18

@ J$0+(2$,& K.,+.0 ($ .33$/%.,1 @#=.,23 L)'/2&(#1 M'

X Cl

X Cl

Ph

OH

SN2

rate-determining

step

X OH

SN1

X

Ph

OH

OH2

or fast

X OH

Ph

rate-determining

step

J2,3' JF> %#$-+3'& . 3.(2$, -'0$3.02R'- #$+,- ()'

8/21/2019 SM-39

9/18

J$0+(2$,& *$# L).%('# HI Y ;'('#/2,2,= #'.3(2$,& /'3).,2&/& 4

=#$+% &2/%01 #'=','#.('& &(.#(2,= /.('#2.09 D( 3.,,$( nY>9 J+=='&( . /'3).,2&/9

Ph Nt-Bu

O H

H2O

PhCHO + t-BuNHOH

5".2)%$ )- &0$ 2.)=*$>

;'-+32,= . /'3).,2&/ *#$/ 2&$($%' '**'3(& .,- ',(#$%1 $* .3(25.(2$,9

!"##$%&$' %)*"&+),E)' 2,5'#&' &$05',( -'+('#2+/ 2&$($%' '**'3( 2,-23.('& &%'32*23 .32-

3.(.01&2& .,- ()' /$-'&( ,'=.(25' ',(#$%1 $* .3(25.(2$, &+=='&(& &$/'

8/21/2019 SM-39

10/18

8/21/2019 SM-39

11/18

J$0+(2$,& *$# L).%('# HI Y ;'('#/2,2,= #'.3(2$,& /'3).,2&/&

8/21/2019 SM-39

12/18

8/21/2019 SM-39

13/18

8/21/2019 SM-39

14/18

8/21/2019 SM-39

15/18

J$0+(2$,& *$# L).%('# HI Y ;'('#/2,2,= #'.3(2$,& /'3).,2&/&

8/21/2019 SM-39

16/18

8/21/2019 SM-39

17/18

8/21/2019 SM-39

18/18

2&,p(9

n2,'(23 2&$($%' '**'3( /2=)( .,- #.3'/2R.(2$, *$# /'3).,2&/ M9 G+( 3)$$&' .

&/.00 &+