Revision of CHIOG
HONC Arrows begin at nucleophiles end at
1 2 34 electrophile
ME
0
Nu Nu E
Bond angles
sp 109.50
sp 1200
sp 1800
Common nucleophiles
water Alcohols organometallic salts
H2O R OH R Mg R Mg
cyanide salts Amines phosphines
0
CEN INR PPh
NaCN KCN
CucN
Common electrophiles
Alkyl halides Gn2 reactions
Br
Goro µ
,carbocations Snl reactions
ti In
carbonyl groups
N
2
Joo YOO
Cahn Ingold Prelog System
Heaviest 1
Anti
R
Opposite side trans
OH f
OH b same side cis
0 fans Iamosietessiadees
, Stereochemistry
Enantiomers Non superimposable mirror images
Diastereomers Not mirror images and cannot be superimposed
Meso compounds Plane of symmetry chiral centres
Functionalisation of alkenes
C C o bond is stronger than C C r bond
H H
H
c C H
En
j
Hi I nd
H H
Bonding electrons are
hard to access Bonding electrons are a lot
easier to access
Electrophilic addition reaction with asymmetrical reagents
H
H H2O
J
y H
Pot t a
H H l 9
h H it 0 H
L t
w
I H2O H Ot
H OH
u
, for
y t
Lt
I Hw
Br
Alkene halogenation addition of Xz alkenes
This results in anti periplanar addition
Not polarised Polarisation 0 Formation of cyclic
f bromium ion
Br Br Br
19 1 Eri
f
H H Orest Br
Y t
c
l f 1 H H H
H H H
I
has lone
ti Ii Bromine ion
pairs so can form
cyclic bromonium ion
r bond electrons which is favored over
can leave if carbocation
needed
H for H
HT T.tl
Anti planar addition Br
Often seen in one
of the most common Bromide can only attack on
polymer productions PVC the opposite face due to
steric hindrance
HONC Arrows begin at nucleophiles end at
1 2 34 electrophile
ME
0
Nu Nu E
Bond angles
sp 109.50
sp 1200
sp 1800
Common nucleophiles
water Alcohols organometallic salts
H2O R OH R Mg R Mg
cyanide salts Amines phosphines
0
CEN INR PPh
NaCN KCN
CucN
Common electrophiles
Alkyl halides Gn2 reactions
Br
Goro µ
,carbocations Snl reactions
ti In
carbonyl groups
N
2
Joo YOO
Cahn Ingold Prelog System
Heaviest 1
Anti
R
Opposite side trans
OH f
OH b same side cis
0 fans Iamosietessiadees
, Stereochemistry
Enantiomers Non superimposable mirror images
Diastereomers Not mirror images and cannot be superimposed
Meso compounds Plane of symmetry chiral centres
Functionalisation of alkenes
C C o bond is stronger than C C r bond
H H
H
c C H
En
j
Hi I nd
H H
Bonding electrons are
hard to access Bonding electrons are a lot
easier to access
Electrophilic addition reaction with asymmetrical reagents
H
H H2O
J
y H
Pot t a
H H l 9
h H it 0 H
L t
w
I H2O H Ot
H OH
u
, for
y t
Lt
I Hw
Br
Alkene halogenation addition of Xz alkenes
This results in anti periplanar addition
Not polarised Polarisation 0 Formation of cyclic
f bromium ion
Br Br Br
19 1 Eri
f
H H Orest Br
Y t
c
l f 1 H H H
H H H
I
has lone
ti Ii Bromine ion
pairs so can form
cyclic bromonium ion
r bond electrons which is favored over
can leave if carbocation
needed
H for H
HT T.tl
Anti planar addition Br
Often seen in one
of the most common Bromide can only attack on
polymer productions PVC the opposite face due to
steric hindrance
