CHM 25500 Lecture Notes - Lecture 32: Thiol, Acid Dissociation Constant, Hydrogen Bond

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CHM 255 - Lecture 32 - Alcohols and Thiols
Alcohols are compounds that contain hydroxyl groups (OH) attached to an sp3
hybridized carbon
Thiols are compounds that contain sulfhydryl groups (SH) attached to an sp3
The parent chain in an alcohol is the longest chain that contains the hydroxyl
The ‘e’ on the end of the name of the alkane is replaced with ‘ol’
Hydroxyl groups always take precedence over other groups (including double
and triple bonds) when numbering the carbons
When numbering cyclic alcohols the numbering always starts with the
carbon attached to the hydroxyl group
Physical Properties
When compared to simple hydrocarbons, alcohols have relatively high boiling
points for their molecular weights
This is because of the type of intermolecular interactions that take place
between the molecules
In simple hydrocarbons, there are only induced dipole interactions between the
In alcohols, however, there are induced dipole interactions as well as permanent
dipole-dipole interactions and hydrogen bonding that occur between the
Acidity of Alcohols and Thiols
Alcohols can function as either weak acids or weak bases
Most alcohols have a pKa of around 16-18
When alcohols are deprotonated it results in an alkoxide ion (strong base)
Alcohols may be protonated by strong acids
When this happens water is produced, which is a very effective leaving
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