E

" CH 2 CH CH 2 !allyl
" CH 2 CH
!vinyl

" "
" # " # #
"& # % $ # # #
#
' # # #

"( (
inhibitor " "
"
)
& $
$
% ) * "
% ) +,
$
H
&
#
% ) F Cl Br I
X2 h
2X 38 58 46 36

X CH 4 CH 3 HX -32 1 16 33
 CH 3 X2 CH 3 X X -70 -26 -24 -20

" $
+ 107 & + 1013
" -
P # # $#

"
"" +0- +-. / $ # ##
&
#
" # #
# 3 2 1 #
"
#
+ *1 / " #
+ 10 +,-- #
# $ CH 3 1 2 3

gauch anti " $ $ stagger

total " $ $ eclipsed
eclipsed eclipsed
#
skew conformers "
stagger )
& ""
*- " CH 2 " $

"&
# # "" (

RhCl 2 PtO 2 "

 " " $ # $
# # # " #
" " "
Mg H 2O
RX RMgX RH MgX(OH)

" )

RX 2Li RLi LiX

2RLi CuX R 2 CuLi LiX
R 2 CuLi 2R 'X 2R R ' LiX CuX

# " $ $ $ #
& 2 "
& ) $
length density $ " ! #
$" )
# " ) #
# &
# # $SR RS $ ( $
- $ # /-3
$ # $ " #
$
R S measured
%ee 100
R S clean

b a bicycle{a,b,c} alkane $ # "

" & c
"
" #
#
* #

"
1,3-diChloroPropane " $ "

#
"
) +/4 CH 2 #

#
# #
) #
& "
" #
#
# " " " *
! " " )" "

# */

# #
) $ $ #
#
# ! # - !
! + " 0 #
! # # #
# & &
" " # ) $ $ #

# "
 # # # "
RX Z RZ X " !
C C R #
X

SN2
$" #
" &
RX 1 2 3 #

# " " ""

SN1
# $" #

# # "
RX R X
#
R OH R OH
" $ $
"" "
$ #
& $" " # " "
$"
RX OH ROH X #
k RX OH # $ # ! #
# " # ( # "
"
strong base
CH 3 3
CH 2 Br SN 2
CH 3 3
CH 2 OCH 2
weak base
SN1
CH 3 C CH 3 OCH 2 CH 3 CH 2 CH 3

( $ ( "
# $ # !
$ " $
# # ( (
 SN1 "
SN2 "
"
SN1 #
SN2 & # $ #
& SN2 $
SN1 # # "& $"
$

) ) " "
" &"OH "
N & "
glycol OH " " "
"
" +-* "
"
(
R
# R
R
# R R
" "
Oxymercuration +
Hydratation 0
Hydroboration *
Hydroxylation
$ /
RX OH ROH X
RX H 2 O ROH HX

# # ,

H 2O
R ' MgX C O R ' CRR '' OMgX R ' CRR '' OH Mg(OH)X
 " +
" 0
" # *
"
"$
/

O C , N C , N C ,S O,O N ,

R-OH +
) $$ & " # " "
! # # "
( "
Sn2 2 Sn1 "
Br "HBr & HCl ZnCl2 #
! " # # #

H C CH 3 2
OH ZnCl 2 H C CH 3 2
O H Zn Cl 2 #

Cl HC CH3 2
ZnCl2 OH $ "

# ( #
Sn2 ( " " " # "
$
# " # & " Sn2 # " "

# $ ( " PX3

R ( R O H PX 2 X

$ # SOX 2 ROH RX SO 2 HX X Cl, Br, I "

( SO2 &
 RO-H 0
1
$ RO ROH M ROM H2 g M Li, Na, K, Mg, Al
2
! NaOH
CH3 CH 2 OH R S O 2
Cl R S O 2
O CH 2 CH3 HCl #

# $

# $R S O 2
O CH 2 CH 3 Z Z CH 2 CH 3 R S O 2

"
"
& KMnO4 " & PCC "
# # " ) "
"

" R-O-R "

& " "

H 2SO4
2ROH R O R H2O
H 2SO 4
CH 3 CH 2 OH 140 C
CH 3 CH 2 O CH 2 CH 3 H2O

( & $
H2SO4
CH3 CH 2 180 C
CH 2 CH 2 H2 O
# # " # $

Sn1 # " # "

Sn2 # & # % "
RX R 'ONa R O R NaX $
" " Sn2 $ $
C CH3 3
Cl NaOCH 2 CH3 C CH 3 2
CH 2 NaCl CH 3 CH 2 OH
 " " $ +
# " Sn2 Sn1
" 0

# & "
"
CH 2 CH 2 R CO O OH RCOOH O +
CH 2 CH 2
" $ concerted $
$ 0
& ( " &
Sn2

# ) +
" Sn1 # " ! # "
! # " (
" OH ) 0
" ( " Sn2 " OH

Alkenes
"SP3 $ SP2 $ $ "
" $ S#
) ,1 5 "
# & #
ene " " " #
"
& # "
#
 "
KOH
CR 2 H CR 2 X ROH
CR 2 CR 2 HX H 2 O +

6 6 #
$" "E2 #

) ,1 "
#
" ( $! "
$ # E+ (
$"
E1-
#
Sn1 " #

E2-
#

" # "C-D C-H # #$ #

#
# # $ "
" ( $
F " ( F
" #
# E1
# " HX # E2
" P # ! #
#
Sn2 # $ Sn2 E2
E2
 # $ # Sn1 E1
(
! " #
CH3 CH 2 OH H 2SO 4
CH 2 CH 2 (140 c)
H
CH3 C OH HCH3 CH 3 CH CH 2
H
CH3 CH 2 C OH HCH3 CH 3 CH CHCH 3 CH3 CH 2 CH CH 2

" " # # +

# & " " "

CH 2 CH 2 H2 CH3 CH3 $ " +
" ""
) ) " # $$ "
) ) " " #
)2) # & " # " 0
( "
# "
OH " *
"
" " " HX

# " " HBr

" OH " H2 " " /
# HX
H # "
CR 2 CR 2 C R 2 CR 2 H
C R 2 CR 2 H X CR 2 XCR 2 H
Oxymercuration ,
NaBH 4
CR 2 CR 2 H OAc 2
H2O CH 2 OHCH 2 Hg OAc CH 2 OHCH 3
NaBH4
CR 2 CR 2 H OAc 2
ROH CH 2 O R CH2 Hg OAc CH 2 O R CH3

CH3 CO O Hg O OCCH3 H2 O CH 3 CO O CH 3 COHg

 CH3 CO O Hg
## #
CH 2 Hg OAc CH 2 OH NaBH 4 CH3CH 2 OH

" &
# $ B2 H 6 # ) " 4

# " " " BH2 BH3

" # $ # " & "
# NaOH
1
" 0
CR 2 CR 2 RC O O OH CH 2 OHCH 2 OH

" (
( # # # "
#
CR 2 CR 2 OsO4 CH 2 OHCH 2 OH
" $ " " !Os
OsO4 $ (
CR 2 CR 2 KMnO4 CH 2 OHCH 2 OH
"
# !' .
$ ) " allyl 3 2 1 CH 3 vinyl
Zn , H 2 O
CH 2 CH 2 O3 CH 2 O O CH 2 $ $ +-

" # & $ $
" $ # " ( #
&" "
( " " $
# $ "
 NMR
# # $ #
" " # #
"

# ""
$ "
& #

#
+2 " 7 "
# & "
" # " #
##
shift download of TMS
ppm
total frequncy

& # " ""

& "
# #
$ " $
" & "
$ $ # J J

"
2 2
" C C Ca $ 0--- # +
# # $
X,W Y,Z
$" # Z Y CHXZ CHYW CHZ CHY CH CH 0
E2

NaNH 2 RX # +
C C H or Na C C Na C C R NaX
# " " # # #
 &" # SP $
H2O RC CR NH3 $
NaOH RC C Na NaNH3 $

SN2
E0
# 0
H2O
RC C C R 2
O R C C C R 2
O R C CC R 2
OH
R "
*
NaOH NaNH 2 H 2O
CH 2 CH 2 X2 CH 2 X CH 2 X E2 CXH CH 2 E2*
H C C Na HC CH

# (
1
R CH 2 C CR 2 B R1C HC CR 2 R1CH C C R2 BH
1 2 1 2 1 2
R HC C CR H B RC C CR H R C C CR H BH
1
RC CCH 2 R 2
Pd,BaSO4 ,H2
RC CR CRH CRH cis
Na,NH3
RC CR CRH CHR trans 78 c

# # &
'
# # /
RC CR X2 CRH CRH cis trans X2 CX 2 R CX 2 R
HX RC CH HX CRX CH 2 ,

# HX
#
# ) # # # 4
#
1
H 2O
RC CH Sia 2 BH RHC CHBSia 2 NaOH CRH CHOH
# # #
/ Sia – Sec Iso Amyl