Alkane

non-polar bonds

weak van der Waal forces

low BP

lipid soluble

neutral

Stable

Alkene

nonpolar

weak van der Waal forces

low BP

lipid soluble

neutral

prone to oxidation

Cycloalkane

nonpolar

weak van der Waal forces

low BP

lipid soluble

neutral

Prone to oxidation leading to peroxide

Aromatic Hydrocarbon

nonpolar

weak van der Waal forces

low BP (but higher than alkanes, alkenes and cycloalkanes)

lipid soluble

neutral

Stable

others to know: Naphthalene (two benzenes), Anthracene (three benzenes), and Phenanthrene (two benzenes with a third catty-corner to it)

Alcohol

polar

H-bond A and D

high BP

water soluble

neutral

stable

Halogenated Hydrocarbon

permanent dipole

weak van der Waal forces

low BP

highly lipid soluble

neutral

stable

Phenol

polar, permanent dipole

H Bond A and D

high BP

water soluble

Acid

easily oxidized to quinones

Ether

polar, permanent dipole

H Bond A only

low BP

lipid soluble

neutral

can oxidize in presence of air

Aldehyde

carbonyl group is polar

H Bond A and D

Higher BP

Water soluble

Neutral

Prone to oxidation

Ketone

Carbonyl group is polar

H Bond A and D

High BP

water soluble

Neutral

Stable

Amine

Polar bond, permanent dipole

1°, 2° H bond donor/acceptor, 3° don't h-bond

moderate to high BP

water solubility (1° > 2° > 3° amines)

Basic (2° > 3° > 1° for alkylamines / aryl decrease basicity)

Carboxylic Acid

polar bond, permanent dipole

H Bond A and D

high BP

water soluble

Acid

Ester

weaker polar, permanent dipole

H Bond A only

low BP

low water solubility

Neutral

easily hydrolized back to carboxylic acid

Amide

polar, permanent dipole

H Bond A and D

higher BP than esters

water soluble

neutral

Carbonate

polar, permanent dipole

H Bond A only

low BP

low water solubility

neutral

Carbamate

polar, permanent dipole

H Bond A only

low BP

water soluble

neutral

Urea

polar, permanent dipole

H Bond A and D

higher BP than esters

water soluble

neutral

stable

Amidine

very basic

Guanidine

very basic

Sulfonic Acid

ion-dipole interactions

very water soluble

strong acid

stable

Sulfonamide

high BP

soluble

weak acid

stable

Thioether

lipophilic

neutral

Nitro

is a charged species

neutral

Epoxide

very reactive due to ring strain

unstable and will react with acid or base in vitro

Aziridine

similar to epoxides with high ring strain

basic

Furan

Looks like ether, but properties are similar to benzene

not very water soluble

neutral

stable

Tetrahydrofuran

water soluble

neutral

prone to oxidation

Pyrrole

aromatic

not water soluble

neutral

Pyrrolidine

a secondary amine

H Bond A only

water soluble

basic

Thiophene

aromatic

not very water soluble

neutral

stable

Oxazole

aromatic

N is an H Bond A

water soluble

N is basic

Isoxazole

aromatic

N is H Bond A

water soluble

N is basic

Imidazole

aromatic

H Bond A and D

water soluble

basic

Pyrazole

aromatic

H Bond A and D

water soluble

basic

Thiazole

aromatic

H Bond A only

not very water soluble

basic

stable

Thiadiazole

can also have the N's on the 2 and 5 positions

aromatic

not very water soluble

stable

Triazole

aromatic

not very water soluble

basic

stable

Tetrazole

aromatic

not very water soluble

basic

stable

Oxazolindin (one ketone)

polar bonds, permanent dipole

H Bond A and D

water soluble

neutral

unstable to acid/base hydrolysis

Oxazolindin (two ketones)

polar bond, permanent dipole

H Bond A and D

water soluble

acid

can form salt with strong base

Hydantoin

polar bonds, permanent dipole

H Bond A and D

water soluble

acid

can form salt with strong base

Pyridine

aromatic

H Bond A only

water soluble

weak base

can form salt with strong acid

Piperidine

aromatic

H Bond A

water soluble

Barbituric Acid

can be substituted in the 5 position to make things like phenobarbitol

strong acid

Indole

Benzimidazole

Purine

multiple H Bond A and D

highly water soluble

Benzodiazepine

will see substituents in the 2 position (to the right of the top N)

Phenothiazine

Amines

Amadine

Guanidine

Aziridine

Pyrrolidine

Oxazole

Isoxazole

Imidazole

Pyrazole

Thiazole

Triazole

Tetrazole

Pyridine

Piperidine

Phenol

Carboxylic Acid

Sulfonic Acid

Sulfonamide (unless N is disubstituted)

Oxazolindin (with two ketones only)

Hydantoin

Barbituric Acid

Alcohol

Phenol

Aldehyde

Ketone

Amine

Carboxylic Acid

Ester (low)

Amide

Carbonate (low)

Carbamate

Urea

Sulfonic Acid

Sulfonamide

Tetrahydrofuran

Pyrrolidine

Oxazole

Isoxazole

Imidazole

Pyrazole

Oxazolindin (both)

Hydantoin

Pyridine

Piperidine

Pyrimidine

Purine

Alkane

Alkene

Cycloalkane

Aromatic Hydrocarbon

Halogenated Hydrocarbon

Ether

Thioether

Furan (not very water sol)

Pyrrole

Thiophene (not very water sol)

Thiazole (not very water sol)

Thiadiazole (not very water sol)

Triazole (not very water sol)

Tetrazole (not very water sol)

Alkene (prone to oxidation to peroxide)

Cycloalkane (prone to oxidation to peroxide)

Phenol (easily oxidizes to quinone in air)

Ether (can form peroxide in air)

Aldehyde (prone to oxidation)

Ester (easily hyrdolized back to carb. acid)

Epoxide (unstable due to ring strain)

Beta Lactam (easily hydrolized b/c of ring strain)

Tetrahydrofuran (oxidation)

Oxazolindin (unstable in acid/base)