Download 07.Chapter7.Alcohols and Related

Organic Chemistry
Chapter 7
Part II
Alcohols, Phenols, and Thiols
Nanoplasmonic Research Group
Chemical Reactions with
Alcohols
• Dehydration to Alkenes
• Conversion to Alkyl Halides
• Oxidation
Dehydration of Alcohols to Alkenes
(E1 or E2)
Protonation of the hydroxyl group
Formation of carbocation intermediate
Beta elimination
The Reaction of Alcohols with Hydrogen
Halides
- Alkyl Halides Formation -
Substitution Reaction (SN1 or SN2)
Nucleophilicity of halide ion is not strong enough for SN2
Please refer to page 219
Another way to alkyl halides!!!
- Treatment with thionyl chloride -
Convert the hydroxyl group to a good leaving
group!!!!
Since hydrogen chloride and sulfur dioxide are
gases and evolve from the product, we don’t
need to separate the desired alkyl halide from
the mixture!!!!
Please take a look at equation 7.33 on
page 221
Why doesn’t phenols undergo the
substitution reactions ?
Why not SN1 ?
Due to extremely unstable phenyl
cation
Why not SN2 ?
Because of the geometry of the ring!!
Oxidation of Alcohols to Aldehydes,
Ketones, and Carboxylic Acids
Primary Alcohol
Aldehyde
Secondary alcohol
Carboxylic acid
Ketone
Please refer to a few reactions on page 222