J

SBWN SBSN WBSN WBWN

Nucleophilicity presence of high electron density
:

Nat HOG IE HzO -

Negative-charged Nu more reactive
DBN MeDe Bro MeOH - Polarizable atoms are more reactive
DBU EtOF Co EtOH ↳
Bigger , more electrons

Xt Rgo - If Nu atoms are the same, basic + reactive

of the base
RSH Basicity Stability
:

HaS ↳ pKa of conjugate acid (SB : pKa < 10)

RNHz BO + HA = HB + At
801Us Base Conj . acid
·
OTs Some just don't protonate (would gain the
00 Tf charges and thus acts as a weak base
Special cases -

Reagent ↳ Resonance stabilized =

Stable =
strong base
-
Cyanide (MBSN)
N = Co 1 Siz Sid > Ez
·
2 3 Ez
:

pKa =
92
.

Special cases
Leaving Group
-

↳
Sulfonate group
OMs OTS OTf 10 SirL> El

: R

RO-S
⑧
1
-

CH3 RO-S
⑧
1
-
EX RO-S
⑧
1

CF
20 E2> Si

330E2
-

! ! !
pka = -1 . 9 pka = -2 . 8 pka = -14

~
E I SBS St -
Benzylic and carbocations can stabilized
WBSN be
10 E2
by resonance and serve as intermediates
20 E2 unimolecular processes :
in

130
S
⑭ *
( Y -
B
~ LG
Neopentyl ,
which
↑
When El product is tri/tetra substituted alkene ,

is a 10 substrate acts ,
as a El favored over Sil
30 substrate
Hydrohalogenation (HX ,
X (1 Br 1)
=
,
,

↳ Markonikov's Rule : In addition of H-X the H adds to the carbon with more H
,
Br
H - (Intermediate could
c
" H-Br
C
a
> C +
Y C
- -

-
H-
H-
undergo rearrangement
=
/
Major Minor
-
Anti-Markovnikov : In addition of H-Br with RO-OR the ,
H adds to the

carbon with less H (Intermediate could

H-H-Br Br

-H # cX undergo rearrangement
&
-
Y -
C
ROOR H-
> C -

-
&
&
H-
/
-
&
Major Minor

Hydration (H-OH)
↳ Addition of OH with an acid the H add to the carbon with
, more H
H-OH H OH H
a H
(Intermediate could
H
C C
-
a
> C &
Y
-
- -

-
H-
H
undergo rearrangement
-C -

HA / &
&
Major Minor

↳ Alcohols can be dehydrated with conc .

H2SOa

YOH
HISO
(conc
&
Li
Oxymercuration -

Demercuration

Hg(OAc) Hg-o
20
H Nu

#Y -

-
(-1)Hg(OAcc
12 NaBHe
,
NucH
&
H
&
-
C -

c
Markornikov Product

Hydroboration
HO
c
H
Anti-Markornikov Product
= CH OH &
H-
C
/
-

↳
Stereochemistry : syn addition
No chiral center : irrelevent , product formed
only one

1 chiral center :
both enantiomers formed
2 chiral centers :
pair of enantiomers formed through syn addition
Hydrogenation (H -H)
↳
Syn addition of H-H in the presence of a metal Catalyst (Pt
, Pd N)
,
:

> =
b ***
-

#*
Halogenation (X-X ,
X (1 =
, Br)
- Anti addition of X-X

#↑ -

Halohydrin (X-X ,
X = (1 , Br ,
1)
-
>
Anti addition of X-X in water or alcohol as solvent

# I
*
Ho
Y

Dihydroxylation
↳
Anti-dihydroxylation
# m
S-

↳
Anti-dihydroxylation
X OH

# mc H

# mcA Solvents
Oxydative Cleavage
&
1 Os
x In/A Y c
.

= = 0 + 0=
2 .
&

1 Os
Y= 12 Y c
.

= 0 + 0=
2 zn. &

Y x =

.
2
y = 0 + 0= c
&