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83 terms

Acidic/ Basic Functional Groups

This only includes the functional groups mentioned in the notes from Dr. Doerksen.
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What is the approximate pKa of a sulfonic acid?
1
What is the approximate pKa of a carboxylic acid?
4-5
What is the approximate pKa of a sulfonylurea?
5.5-8
What is the approximate pKa of an aromatic sulfonamide?
7-9
What is the approximate pKa of an imide?
8-10
What is the approximate pKa of a phenol?
10
What is the approximate pKa of a catechol?
10
What is the approximate pKa of a resorcinol?
10
What is the approximate pKa of a hydroquinone?
10
What is the approximate pKa of a primary amine?
9-10
What is the approximate pKa of a secondary amine?
9-10
What is the approximate pKa of a tertiary amine?
9-10
What is the approximate pKa of a pyrrolidine?
9-10
What is the approximate pKa of a piperidine?
9-10
What is the approximate pKa of a piperazine?
9-10
What is the approximate pKa of a morpholine?
9-10
What is the approximate pKa of a tetrahydroisoquinoline?
9-10
What is the approximate pKa of an aniline?
4-5
What is the approximate pKa of a pyridine?
4-5
What is the approximate pKa of a quinoline?
4-5
What is the approximate pKa of a benzimidazole?
4-5
What is the approximate pKa of an isoquinoline?
4-5
What is the approximate pKa of a pyrazole?
2-3
What is the approximate pKa of a thiazole?
2-3
What is the approximate pKa of a pyridazine?
2-3
What is the approximate pKa of a imidazole?
6-7
Are alcohols acidic, basic, or neutral?
neutral
Are phenols acidic, basic, or neutral?
acidic
Are ethers acidic, basic, or neutral?
neutral
Are primary amines acidic, basic, or neutral?
basic
Are secondary amines acidic, basic, or neutral?
basic
Are tertiary amines acidic, basic, or neutral?
basic
Are aromatic amines acidic, basic, or neutral?
basic, but significantly less so than non-aromatic amines
Are carboxylic acids acidic, basic, or neutral?
acidic
Are esters acidic, basic, or neutral?
reactive, but neither acidic nor basic
Are amides acidic, basic, or neutral?
neutral
Are thioethers acidic, basic, or neutral?
neutral
Are sulfonic acids acidic, basic, or neutral?
acidic
Are sulfonamides acidic, basic, or neutral?
acidic
Are sulfonylureas acidic, basic, or neutral?
acidic
Are pyrroles acidic, basic, or neutral?
neutral
Are pyrrolidines acidic, basic, or neutral?
basic
Are thiophenes acidic, basic, or neutral?
neutral
Are tetrahydrothiophenes acidic, basic, or neutral?
neutral
Are imidazoles acidic, basic, or neutral?
basic
Are pyrazoles acidic, basic, or neutral?
basic
Are imidazolines acidic, basic, or neutral?
basic
Are imidazolidines acidic, basic, or neutral?
basic
Are oxazoles acidic, basic, or neutral?
neutral at physiological pH
Are isoxazoles acidic, basic, or neutral?
basic
Are 2-oxazolines acidic, basic, or neutral?
basic but unstable to acids
Are oxazolidines acidic, basic, or neutral?
basic but unstable to acids
Are thiazoles acidic, basic, or neutral?
basic
Are triazoles acidic, basic, or neutral?
basic
Are tetrazoles acidic, basic, or neutral?
basic, but with 1 acidic nitrogen
Are pyridines acidic, basic, or neutral?
basic
Are piperidines acidic, basic, or neutral?
basic
Are pyrazines acidic, basic, or neutral?
neutral at physiological pH
Are pyrimidines acidic, basic, or neutral?
basic
Are pyridazine acidic, basic, or neutral?
basic
Are piperazines acidic, basic, or neutral?
basic
Are morpholines acidic, basic, or neutral?
basic
Are uracils acidic, basic, or neutral?
basic
Are thymines acidic, basic, or neutral?
basic
Are cytosines acidic, basic, or neutral?
basic
Are indoles acidic, basic, or neutral?
neutral
Are benzimidazoles acidic, basic, or neutral?
basic
Are benzoxazoles acidic, basic, or neutral?
neutral at physiological pH
Are benzthiazoles acidic, basic, or neutral?
neutral at physiological pH
Are purines acidic, basic, or neutral?
basic
Are adenines acidic, basic, or neutral?
basic
Are guanines acidic, basic, or neutral?
basic
Are xanthines acidic, basic, or neutral?
basic
Are quinolines acidic, basic, or neutral?
basic
Are isoquinolines acidic, basic, or neutral?
basic
Are tetrahydroisoquinolines acidic, basic, or neutral?
basic
Are imides acidic, basic, or neutral?
acidic
Are catechols acidic, basic, or neutral?
acidic
Are resorcinols acidic, basic, or neutral?
acidic
Are hydroquinones acidic, basic, or neutral?
acidic
Are anilines acidic, basic, or neutral?
basic
Are bisanilines acidic, basic, or neutral?
neutral at physiological pH
Are phenothiazines acidic, basic, or neutral?
neutral at physiological pH