Organic Chemistry: Functional Groups and Acidity
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The pKa of HCl is approximately \(-7\), indicating it is a very strong acid.
α-protons acidity order: aldehydes > ketones > esters > amides.
The pKa of water is approximately \(0\).
A primary alcohol has the structure OH attached to a carbon bonded to one other carbon (R-CH2-OH).
Phenol has a pKa around \(9-11\), making it more acidic than typical alcohols.
This is a ketone, characterized by a carbonyl group bonded to two carbon atoms.
Carboxylic acids have a pKa around \(4-5\), indicating moderate acidity.
A tertiary amine has a nitrogen atom bonded to three carbon groups and no hydrogen atoms (R3N).
Terminal alkynes have a pKa around \(25\), showing relatively acidic C-H bonds.
This is a carboxylic acid, containing a carbonyl and hydroxyl group on the same carbon.
Amides have a pKa approximately \(15-16\), less acidic than carboxylic acids.
An ether has an oxygen atom bonded to two alkyl or aryl groups (R-O-R').
Thiols typically have pKa values around \(10-12\), similar to phenols.
This is a nitrile, characterized by a carbon triple-bonded to nitrogen.
α-protons of aldehydes have pKa values around \(17-20\), more acidic than ketones.
A nitrogen atom bonded to four alkyl groups carrying a positive charge (R4N+).
Alkanes have very high pKa values, typically > \(60\), indicating very weak acidity.
This is an ester, with a carbonyl adjacent to an ether oxygen.
Secondary amines have pKa values around \(33-40\), indicating weak acidity.
An anhydride consists of two acyl groups bonded to the same oxygen atom (R-CO-O-CO-R').
Ketones have α-proton pKa values around \(20-25\), less acidic than aldehydes.
A primary halide has a halogen atom bonded to a carbon attached to only one other carbon (R-CH2-X).
Secondary thiols have pKa values similar to primary thiols, generally around \(10-12\).
This is a nitro group, with nitrogen bonded to two oxygens and one carbon.
Primary amines have pKa values around \(33-40\), indicating weak acidity.
A sulfur atom bonded to two alkyl or aryl groups (R-S-R').
Esters have α-proton pKa values around \(25-30\), less acidic than ketones.
A tertiary alcohol has the hydroxyl group attached to a carbon bonded to three other carbons (R3C-OH).