Class notes

Organic Reaction Mechanisms - Organic Chemistry

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Course
CHEM 281 (CHEM281)

Institution
Simon Fraser University (SFU )

Class notes from lectures on organic reaction mechanisms. Includes acid-base, substitution, rearrangement, addition, and elimination reactions.

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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 18

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ORGANIC

Le M IS
MPORTAN TO UNDERSTAND REACTION MECHANISMS BECAUSE
THEY TELL US
WHY And How A REACTION OCCURRED . REACTION MECHANISMS SHOW THE

MECHANISMS Specific and Sequentral MOVEMENT of ELECTRONS
during
A CHEMICAL REACTron This MOVEMENT S
.
REPRESENTED By CURVED ARROWS THAT MUSTRATE

ELECTRON MOVEMEN FROM NUCLEOPAMES TO
ELECTROPHITES .

DENSE MOLECULES WITH ELECTRON RICH ACOMS THE USUALLY HAVE Of
VEOPHMES : ARE ELECTRON IONS OR . ONE OR MORE

The
FOLLOWNG TRLE Bond
A

MEGATE CHARGE
THE CHARACTERESTS A LONE C-C DOUBLE Or To Reactne
.
,
Pors ,

St
ELECTRONS THE BOND HEY ARE NUCLEOPHUES FOR +
k
++
PARTICIPATING
THE ATTRACTED
N .
T CALLED
WAY THEY ARE TO
POSTNELY
S-
NUCLEi
CHARGED
.

ELECTROPHIES ELECTRON ICNS OR MOLECULES W I ELECTRON POOR ACOMS HAVE POSTAE
CHARGE
: POOR A OR
PARTHAL POSTME
THEY
.

DUE TO
DiPOLES CAUSED
By POLAR Bowds
.

T SEE
Exactly How MOLECMES REACT WITH ONE ANOTHER, WE DRAW

ELECTRON MOVEMENT lice How do for Acro-base and resource.
Ayamo
ELECTRONS MOVE NO 3 curved Arrows we
CAN
ONLY WAYS
:
,

H C

Of ELECTRONS
domNG
,

forming
Bond
...
. When A Love par The
Contributes to By : THESE CURVED ARROWS DEPRET THE MOVEMENT A REACTRON
BF3
=
1 > .

H
,
C
H a
,

formation of A NEW Bond n The product
. THERE ARE RULES To Curved Arrows THE HEAd of THE Arrow

DRAWG
.

H HzC
2 Bond WHER A Bond CHX B PONT THE DIRECTION of ELECTRON of
oo

The Reactant MOVEMENT
BrEakmg
MUST THE Arrow
.
=
present N CH Br : 2 : I .
THE TAR
6 o

7
HzC HC
,
BECOMES A LONE OF ELECTRONS THE PRODUCT The ELECTRON Source
AddMrovay Curved Arrows are

Begno
Musy
PANR TN .
& , ,

H

Hay-
It

I
. Bond
3 Bond Bond THE REACTANT SHOW AOM MOVEMENT
A ELECTRON MOVEMENT
THEY
To WHEN NOT USED To
Only
= No
B t
.

2
H
-

It ItzC
is Broken no favour of formaron of a Bord It -
AllyS Pony To ETHER An AcoM Or A Bond, N O MTO
/
EmpTy SpACE .

of Formal
product KEEP
Charges
in the TRACK .

RXN
INTERMOLECULAR REACTIONS : ARE REACTIONS THAT
Types Summary
O COR BETWEEN 2 OR MORE MOLECULES Acid-BASE REACTIONS Addnon REACTIONS - 1 OR 2 STEPS

Br
S

Bi Br
H Br
%. + H +
Nai ↑
- ot
.. >
+ -
② H
7
8+ ↓ O

SUBSTAUTON REACTIONS -1 OR 2
STEPS ELIMINATION REACTIONS - 1 OR 2 STEPS

U Br
& TRAMOLECULAR REACTIONS : ARE REACTIONS THAT
Br +
-
- -
c
+ BrNa" + -
CHz > + Brivat

Nat Nat

Smogle
Occur WITHIN A MOLECULE

o- T
S 3
J ·
+
p Rearrangement
REACTIONS

Off
-
2
Steps
TYPReL INTERMEdrATES :
⑧
O

1 CANTON-HAS An
.

METHYL EMPTY PORBMAL THAT

H
WES
PerpendICULAR TO THE

# t

METHYL PLANE . 2-H Bowds

ARE
Sp3-S OVERLAP .

2
.
METHyL Anton - has a Lone
par no A Sp3

ORBMAL THIS AREA
↑
.
IS
VERY
H H
H
ELECTRON DENSE DUE TO THE

LOVE PAR

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