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Chapter 10
Reactions of Alcohols,
Amines, Ethers,
Epoxides, and
Sulfur-Containing
Compounds
Fill in the Box with Reaction Conditions or Product
Do not confuse SN2 reactions
for a German SN2 which was
used as a radar system in WWII
The Artificial Sweetener Splenda (Sucralose)
Could Splenda be a cellular alkylating agent?
No, it is too polar to enter a cell.
Provide Correct Reagent/Reactant/Product
Provide Correct Reagent/Reactant/Product
Meep-Meep is trying to perform and E1 reaction but
has come up with a strange and unexpected product.
Give a mechanism to explain his reaction.
Mechanism:
Meep-Meep
Chromium Oxidation Mechanism
(via Chromic Acid)
Na2CrO7 – Precursor to H2CrO4
Mechanism:
CrO3 – Precursor to H2CrO4
PCC – Mild Oxidant
List all potential reagents used for oxidation and if a
ketone, aldehyde or carboxylic acid is generated.
Benzoic Acid is used
As a preservative to prevent
against bacterial and fungal
growth. It’s added to many
drinks including Diet Coke.
Quinone functional group
used in the living organisms to
perform oxidations with in
cell. So your body also does
oxidations as we speak.
Citral is produced by lemons
naturally and smells like
lemon peels. Used in the
perfume industry to make
nice smelling oils.
Bodies Natural Oxidation: Alcohol Dehydrogenase
Too much ethanol
In system effects
the nervous system
and results in
becoming “drunk”
The headache of a
“hangover” is the
result of too much of
toxic acetaldehyde in
ones system.
Human Liver
contains both
Alcohol and
Aldehyde
Dehydrogenase
Alcohol
dehydrogenase
Aldehyde
dehydrogenase
For Each of the Below: Indicate Reaction
Condition and Predict the Product
Acid monster from the 50’s
Smoking and Cancer
Not all smokers
get cancer
Benzopyrenes in chimneys
were responsible for cancer of
the scrotum in “chimneyboys.” The connection
between cancer and chimney
soot was made by Percivall
Pott in 1775.
11
Arene oxides as a carcinogen:
DNA
backbone
12
Benzene is also a Carcinogen
Before the discovery
of the health hazards
of benezene,
mechanics would
routenely wash
object with benezene
including their hands!
Predict the Product for Each Reaction
The nasty smell of a dirty trash can
or rotting meat is attributed mostly
to amines and sulfur containing
molecules. As you now know, these
molecules are great at SN2 Nu’s and
can do reactions in your body! Your
nose is likely warning you of that!
This product gives the
smell of garlic … you
could make it in lab.