Class notes

Alkyne Reaction Mechanisms - Organic Chemistry

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Course
CHEM 281 (CHEM281)

Institution
Simon Fraser University (SFU )

Condensed class notes for lectures about organic synthesis and transforming alkynes. Includes synthesis of aldehydes and ketones using markovnikov and anti-markovnikov addition reactions.

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Uploaded on January 18, 2024
Number of pages 2
Written in 2023/2024
Type Class notes
Professor(s) David vocadlo
Contains Class 25

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TRANSFORMING AlkyNES
NEED A GOOD MELLEOHME,

STRONG
BASES ARE MOLECULES THA
CREATE An
AlkyC Now from Bre-
+
conj
Acid
REALLY WANT THAT AddMIONAL
PROTON
.
AN ALKENE WH Strang The
DeProTorre : - Vane Or RCEC-ARE Both
good
ArgHER PKars BETTER .

AlkyNE IS Now
ASTRONG MeleopHE .

WANT AN ALKENE OR
ALIANE
Buy Have Hz
D REE Of Reduction
An
AlkynE ? Limolar's
Eg
REDUCE THAT
AlkyNE WITH:
Da CATALYST

A
VARIES
ON
DEPENDING
REACTray
of
attryere
Hydrog
ENTON :
METAL CATALYST
.

Very Smar Hydrogenation
To Hz LESS ACTIVE = LESS
>
of ALKENES pd Reduction
.
Da .

d

ELECTROPHMIC AddNON W/ALkyNES

↓
of
2 Molecules
Hydrogen
Br
H-Br ...
H
Requires
Hydrag -
>
.
-

H-Br
EN HALiDE Da
S
>
Da HALidE for .
REACTION
Da ..............
ADDDION : A
Br CREATES A HALOALIENE from
An
AlkynE

HHz GMES And Ever from an Alkyne
Acid CALyZED -1 - OH

Acid And .
WHER
En

-my
-

Da
-

i Da Da

BE FURTHER TRANSFORMED
HydRATON :
H20
1
CAN
into A KETONE
Da
Ot

OxymerCuration/ GNES A MURCORIC NTERMEONATE
- Hg(OAc)2
REDUCTION : Da Hg(Ad 2

Hz0 HySOu
,
-
-"glacan
2 Da
S

Off
WHICH CAN THEN BE USED TO MAKE
A KETONE
.

-
GIVES A BORANE INTERMEDATE
Hydroboration
BHz
THAT CAN BE USED TO MAKE AN
odaron : Da
Da ALdEltydE
BHz

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