Summary Organic and Biosynthesis - Organic chemistry part (WBFA008-05)
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Course
Organic and Biosynthesis (WBFA00805)
Institution
Rijksuniversiteit Groningen (RuG)
A comprehensive summary of the organic chemistry part for the course Organic and Biosynthesis. It contains all the information from the lectures and tutorials, and sometimes the book is also covered.
de / ocalized electro ns result from the P Orbital Of One
atom
overlapping the porbitals of twoadjacent Atoms
> resonance
Atomic Orbital =
region of Space arouna the nucleus wnere maria
an electron is mostapt to be found ' '
( complete octet )
4 z
Drawing resonance :
electro ns cannot moue to an sp Carbon
¥1
•
P Orbitals 3 Zpx / 2 / zpz
→ :
Py •
double
× double single bond → al / atoms have empty p Orbit als
-
/
-
↳ if 2 Overlap → 1T bond ↳
zpx Orbital
}
Stability
•
Sp Orbital due to nybridization
}
1 SP
109.5° ga Separate d charges
°
>
( ,
incomplete octet ,
or a positive charge on an electro negati
j
_
• 0 bond
,☐
g. g-
g⑦
atom ( or vice versa ) makes a compound ¥ stable
°
The stable resonance Contributions the the delocalization En
• ?
Orbital double bond
moore ,
greater
Sp :
> 0 bond
b Sp
'
-
s / Sp
'
overlap
0④0 \
④
↳
contributies more to hybrid
ÈÏÏ }
1T bond °
' ( diene
„ 6.60 onjugateddiene more stable than isolated
> 1
,
CIC overlap
- -
overlap
>
IS >
electron de/ ocalization ( resonance )
180°
>
hybridization of Orbit als
Chapter
°
5 relative Stability of carbocations :
Ëf
lea
ÉRR Én
" °"
stable ÈHZ = (Hr = CHÉHZ =
R , r -
> R -
> H -
> ( H2 = ÉH S
positive charge
-
>
Electropnile Parti at positive Or an
charge
=
,
, .
benul " "
4 '
metny ,
vinyl
cation cation tertiary Secondary primary
carbokation cation cation
carbokation carbokation
incomplete octet
↳
Substituten of -
R makes more stable
>
nucleophile Negative charge Lone pair it
=
,
or a bond °
Delocalized electro ns pka acid → release of proton like
towers →
Stronger more
↳ electron s to share
'
arrows from nucleophile → electro phik →
important
>
reaction coorainate diagram shows energy Changes
-]Ë
9 Íation
-
DÉ Electronic Effects
Es
'
A- - - -
Ter-94 lrineti
"
kinetic Stability :
[
0
Ë
'
free °
+
Electron donation
•
( enermoaynam.is )
o energy B ↳
stable
destabilizes the base → decreases acidity 2
genant Large -1 Slow
=
-
- -
'
± :
Electron withdraw at stabilis.es →
aciaity
°
the base increases z
thermodynamicaability : DÓ
reaction progress Inductie electron
°
withdraw at withdrawat of electrons bond
through 0
=
↳ is stable
Negative product
=
>
substituent to ( ÙHS)
benzene
ring moreel
ectronegatiue than
hydrogen
> transition state (t ) → partieel bonds +
charges °
Electron (
donationbyhyperconjugation-donatingelectrons.to a p Orbital
highest energy DÉ
>
rate limiting step Slowestkinetics
= =
°
Electron donati on by resonance =
substituent with lone pair on atom at
Ched to benzene
ring → Ione pair can be delocalized into ring ( NH2.OH.C
Chapter 6 '
also withdraw electro ns inductiveiy ( more electro
negatie )
> Substitute ons
'
( R) stabilize compound
°
Electron withdraw at substituent to ring aoublyltriplybon
-
a resonance is
by
=
R "
R -
CÉR Moore stable than R -
[
É H
to amore electro
negative atom → electrons from ring onto substituent (( = 0
withdraw electro ns inductiveiy ( more
negatie )
> also electro
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