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CH107 - Organic Chemistry
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Following document includes REACTION MECHANISMS, definitions, explanations, prequisites and a lot more !! - Describing Polar Organic Reactivity and Stereochemistry - Functionalisation of Alkenes - Organometallic Nucleophiles - Reactions of Epoxides - Synthesis and Reactivity of Carbonyl Com...

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  • March 15, 2021
  • 45
  • 2020/2021
  • Lecture notes
  • Dr. sarah walker
  • All classes

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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

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