Class notes

Resonance - Organic Chemistry

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Course
CHEM 281 (CHEM281)

Institution
Simon Fraser University (SFU )

Condensed class notes for lectures about resonance in organic chemistry. Includes rules for resonance and patterns to look for.

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Uploaded on January 18, 2024
Number of pages 1
Written in 2023/2024
Type Class notes
Professor(s) David vocadlo
Contains Class 6 to 8

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BOLW ↓
Aromaticity
DELOCALIZED ELECTRONS : WHEN ELECTRONS ARE NEY CONFINED TO A ATOM OR BOND DELOCALIZATION INCREASES
STABAMY
SINGLE
,
,

Resource Structures Allows deLocated ELECTRON And Modern Thi HOW

Drthny
See WHERE are
Us To
They

RESONANCE FORMS DO NOT EXIST AS N Rules For
CHARGE
DELOCATED HOWEVER . ,
DISTINLT Species . OVERALL
CONNECTNy Remem

CONSTANT .
Resonance :
look for Resonance Hybrids
WErgHED Average
are a
IMPORTANT PATTERNS To
IT Bond Beside An Acom With A Love
1 Park : of RESONANCE STRUCTURES BASED ON THEIR . RESONANCE FORMS HAVE
COMRIBEMY
1 No REAl ExiSTENCE

.
2 Or iT Bond RESONANCE
STABMAY LONE Parr ELECTRONS In

·
.
only

C H T
g STRUCTURES

H Oa
+
-
H
&
H O 3
. so
HyperValent 2nd Row CLEMENTS

Structurer structure
4
. MUST HAVE ORBAL
· E OVERLAp

Love PAR Beside An ACOM W/OO A full OCTET MORECUTE'S
ENERGY
.
2 . DELOCALMATTON LOWERS
5

.
6
H EquratEn STRUCTURES MAKE
EquNALENT CONTRIBUTIONS
H H
H
CN : -
REPRESENTED BY TWO STRUCTURES INSIDE BRACKETS WHE MORE STABLE STRUCTURE MAKES A
SQUARE LARGER
+

C N
H
It H
H
MOVENTAG
WITH AN ARROW RESONANCE . COVED CONTRIBUTON OTHERWISE

ARROWS ARE USED TO SHOW ELECTRON CELOCALIZATION .
. THE MORE CONALENT
7 BONUS A STRUCTURE HAS, THE MORE STABLE

Bonds
.
3 Two Or MORE
Adjacent # is

H
.
8 Full VALENCE SHELLS ARE MORE STABLE THAN deficient ONES
H It
.

H
I
H It

C
C
T
C
H C C
·
O
It .
9

CHARGE Separation
decreases
STABrMy
+ C C
-

for Apart
Charges
Witnes: Like
It
H It

Oppose
CHARGES
close-

10
. NEGAINE CHARGE ON MORE ELECTRONEGAINE ATOM .

RESONANCE & REACTIONS : RESONANCE of A MOLECULE CAN TELL US A LOT ABOUT HOW I WILL REACT
.

# HAS An Effect On REACTONY & Rate of REACTION .
MotECUTES WHOU RESOMANCE ARE LESS STABLE SNCE ELECTRON

DELOCALIZATION ACTS MOLECMES WMHOU RESONANCE ARE MORE REACTNE HOWEVER THIS
CHARGES
TO STABMAE . .

STABMTEATON Of
CHANGE
ALLOWS REACTIONS TO
PROCEED FASTER THAN
THEY Would OTHERWISE AROMATICMY-BENZENE : BENEEME is PLANAR ,
Cyclic And , SACRATED
.

of BENLENE doubled
HavingAlternating
is THAT
DESPHE
INTERESTAGquarry
An

Bonds Bards .
LEngTH STRENGTH
ALL THE CARBON-CARBON Are a
EquanaLent
in

SINGLE
,

i s BECAUSE BENZENE
THIS is A
Hybrid of TWO RESOMANCE STRUCTURES CALLED KEKULE

Bonds Between & double C-c Bonds
Single
Structures . All are in

Enga
Streng Bonds
I
TEORETICALLY BECAUSE DOUBLE ARE SHORTER THAN Bonds THE
Sigle
, ,

CycoHExATRENE PREDICTED STRUCTURE of BENEME Should Be THE of ALL THE c-cBowds
,
Less
Regular
.

EquUMENCE

STRUCTURE of Benzene, much is a indication of resource

strong
.

LESS STABLE .

E >

Benzene KEKvE STRUCTURES

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