6M1X0 - Notes Organic Chemistry
, Mechanismes
Nucleophilic substituties : SNI & SNZ
GRÉ
R
Nut + c- ✗
Nu (
'
1×-0
gr pt
>
-
SNI :
1µF +
it +
1×-0
R
'
frïïï)
sie R
,
Visualisiny mechanisme :
1 .
Energy Landscape : The Poth of Lower
energy .
↳ SNI is Curved Poeth, SNZ straight
2 . Reaction coördinatie -
energy plot
3 . Curved arrows
Arrows
> reaction
>
< ( 4 ualdbrium
< >
resonance
V Movement of Electron pairs
I Movement of an electron
• Follow octet tule
•
Arrows always start from a Lone pair
↳
becomes : free pair, Bond .
ÂIn
It is easy to remove a proton from this molecule because a resonance Structure is possible
È y
< >
Additions of hydroy@nhaiide.s to an alkenen
( H> ( H = CMCM + H -
511 > CH} CHCHZCH} +
}
- ← +
→ ( H> ( H -
CHZCH}
de
\
.
H+ adds to the alkene to form the host stable cation .
Stabilitìes of cations
RÌIH
R
CÉR
R " "
R , _ least
host stable
_
> (④ > > j
|
Stable
' ' '
r m m H
ij ij
, Resonance & shifts
•
Pi -
bonds
Hyperconjugation Resonance
•
:
invoering Sigma bonds
in
HET HEÍTI % ÊHCH
He den
( H [ →
g- GH →
- -
-
> > ,
µ
-
( H}
1,2 hytfdride shift ¢
* also possible for alkyl groups
ÇM} M in }
* Shift only happens it it qivesamore
'
µ> ( -
( -
c -
en } M> c-
Ç
-
CHZCH
}
' '
stable cation immediately µ Br
.
p,
* hydride shift is easier than an alkyl shift .
minor product Major product
Reaction s of alkenes with halides
-
Hz ( = ( Mz → Hç -
( blz +
Er, -0 → Hzc -
(
Hz
ÊÎ \
pr s
/
ioaacside
attack
% Ï
[ opposites backside attack)
(
à: ④ Always
No rearranyements in the carbocation .
Check for reaction with that
for terminal
ALKYNE addition aiicynes .
Using acid ( atalysed water
µ(
HÂÒIH
( Hgc = ( µ
"250 "
> ( H
}
( = Hz → CH
}
( CH
}
"
PmueophiletltattaiksheretEMF-qj.tl o
For terminal alkltnes : µ; YN
H> Ö
( MECH ) (H ( Äʵ > (H > ( = en + { → (H ( = CH +
t n/
>
ÂW
>
' '
↳ Hg④
'
!"
µ -
< en
}§Ä Hgt
(H>
fn } ( H> ⇐ ( H2
"
om
] +
Ketone H - -0 -
H
'
m
µ ging hydroboration : \" " -
"" " ° " aldehyde
"3C /
H 04
,q
( H} ( ICH > =L y ( µ, = 'en > ( HZÇHZCH
THF µ
RIB -
R
Using Hz
H'
(H> ( ICH > ( H> ( HZCH
Pd /C }
ij
ijij ijij
, Mechanismes
Nucleophilic substituties : SNI & SNZ
GRÉ
R
Nut + c- ✗
Nu (
'
1×-0
gr pt
>
-
SNI :
1µF +
it +
1×-0
R
'
frïïï)
sie R
,
Visualisiny mechanisme :
1 .
Energy Landscape : The Poth of Lower
energy .
↳ SNI is Curved Poeth, SNZ straight
2 . Reaction coördinatie -
energy plot
3 . Curved arrows
Arrows
> reaction
>
< ( 4 ualdbrium
< >
resonance
V Movement of Electron pairs
I Movement of an electron
• Follow octet tule
•
Arrows always start from a Lone pair
↳
becomes : free pair, Bond .
ÂIn
It is easy to remove a proton from this molecule because a resonance Structure is possible
È y
< >
Additions of hydroy@nhaiide.s to an alkenen
( H> ( H = CMCM + H -
511 > CH} CHCHZCH} +
}
- ← +
→ ( H> ( H -
CHZCH}
de
\
.
H+ adds to the alkene to form the host stable cation .
Stabilitìes of cations
RÌIH
R
CÉR
R " "
R , _ least
host stable
_
> (④ > > j
|
Stable
' ' '
r m m H
ij ij
, Resonance & shifts
•
Pi -
bonds
Hyperconjugation Resonance
•
:
invoering Sigma bonds
in
HET HEÍTI % ÊHCH
He den
( H [ →
g- GH →
- -
-
> > ,
µ
-
( H}
1,2 hytfdride shift ¢
* also possible for alkyl groups
ÇM} M in }
* Shift only happens it it qivesamore
'
µ> ( -
( -
c -
en } M> c-
Ç
-
CHZCH
}
' '
stable cation immediately µ Br
.
p,
* hydride shift is easier than an alkyl shift .
minor product Major product
Reaction s of alkenes with halides
-
Hz ( = ( Mz → Hç -
( blz +
Er, -0 → Hzc -
(
Hz
ÊÎ \
pr s
/
ioaacside
attack
% Ï
[ opposites backside attack)
(
à: ④ Always
No rearranyements in the carbocation .
Check for reaction with that
for terminal
ALKYNE addition aiicynes .
Using acid ( atalysed water
µ(
HÂÒIH
( Hgc = ( µ
"250 "
> ( H
}
( = Hz → CH
}
( CH
}
"
PmueophiletltattaiksheretEMF-qj.tl o
For terminal alkltnes : µ; YN
H> Ö
( MECH ) (H ( Äʵ > (H > ( = en + { → (H ( = CH +
t n/
>
ÂW
>
' '
↳ Hg④
'
!"
µ -
< en
}§Ä Hgt
(H>
fn } ( H> ⇐ ( H2
"
om
] +
Ketone H - -0 -
H
'
m
µ ging hydroboration : \" " -
"" " ° " aldehyde
"3C /
H 04
,q
( H} ( ICH > =L y ( µ, = 'en > ( HZÇHZCH
THF µ
RIB -
R
Using Hz
H'
(H> ( ICH > ( H> ( HZCH
Pd /C }
ij
ijij ijij
