Functional Groups Test Questions – Flashcards
Unlock all answers in this set
Unlock answers| -CH3 |
Alkane non-polar bonds weak van der Waal forces low BP lipid soluble neutral Stable
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| =CH2 |
Alkene nonpolar weak van der Waal forces low BP lipid soluble neutral prone to oxidation |
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Cycloalkane nonpolar weak van der Waal forces low BP lipid soluble neutral Prone to oxidation leading to peroxide |
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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) |
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Alcohol polar H-bond A and D high BP water soluble neutral stable |
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Halogenated Hydrocarbon permanent dipole weak van der Waal forces low BP highly lipid soluble neutral stable |
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Phenol polar, permanent dipole H Bond A and D high BP water soluble Acid easily oxidized to quinones |
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Ether polar, permanent dipole H Bond A only low BP lipid soluble neutral can oxidize in presence of air |
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Aldehyde carbonyl group is polar H Bond A and D Higher BP Water soluble Neutral Prone to oxidation |
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Ketone Carbonyl group is polar H Bond A and D High BP water soluble Neutral Stable |
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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) ; ; ; |
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Carboxylic Acid polar bond, permanent dipole H Bond A and D high BP water soluble Acid |
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Ester weaker polar, permanent dipole H Bond A only low BP low water solubility Neutral easily hydrolized back to carboxylic acid |
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Amide polar, permanent dipole H Bond A and D higher BP than esters water soluble neutral |
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Carbonate polar, permanent dipole H Bond A only low BP low water solubility neutral |
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Carbamate polar, permanent dipole H Bond A only low BP water soluble neutral |
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Urea polar, permanent dipole H Bond A and D higher BP than esters water soluble neutral stable |
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Amidine very basic |
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Guanidine very basic |
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Sulfonic Acid ion-dipole interactions very water soluble strong acid stable |
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Sulfonamide high BP soluble weak acid stable |
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Thioether lipophilic neutral |
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Nitro is a charged species neutral ; |
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Epoxide very reactive due to ring strain unstable and will react with acid or base in vitro |
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Aziridine similar to epoxides with high ring strain basic |
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; Beta Lactam easily hydrolized in aqueous solutions b/c of ring strain ; |
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Furan Looks like ether, but properties are similar to benzene not very water soluble neutral stable |
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Tetrahydrofuran cyclic ether water soluble neutral prone to oxidation |
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Pyrrole aromatic not water soluble neutral |
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Pyrrolidine a secondary amine H Bond A only water soluble basic |
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Thiophene aromatic not very water soluble neutral stable |
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Oxazole aromatic N is an H Bond A water soluble N is basic |
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Isoxazole aromatic N is H Bond A water soluble N is basic |
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Imidazole aromatic H Bond A and D water soluble basic |
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Pyrazole aromatic H Bond A and D water soluble basic |
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Thiazole aromatic H Bond A only not very water soluble basic stable |
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Thiadiazole can also have the N's on the 2 and 5 positions aromatic not very water soluble stable |
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Triazole aromatic not very water soluble basic stable |
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Tetrazole aromatic not very water soluble basic stable |
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Oxazolindin (one ketone) polar bonds, permanent dipole H Bond A and D water soluble neutral unstable to acid/base hydrolysis |
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Oxazolindin (two ketones) polar bond, permanent dipole H Bond A and D water soluble acid can form salt with strong base |
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Hydantoin polar bonds, permanent dipole H Bond A and D water soluble acid can form salt with strong base |
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Pyridine aromatic H Bond A only water soluble weak base can form salt with strong acid |
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Piperidine aromatic H Bond A water soluble |
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Barbituric Acid can be substituted in the 5 position to make things like phenobarbitol strong acid |
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Indole
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Benzimidazole
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Purine multiple H Bond A and D highly water soluble |
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| Quinoline |
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Benzodiazepine will see substituents in the 2 position (to the right of the top N) |
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Phenothiazine
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| Catechol |
| Basic Functional Groups |
Amines Amadine Guanidine Aziridine Pyrrolidine Oxazole Isoxazole Imidazole Pyrazole Thiazole Triazole Tetrazole Pyridine Piperidine
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| Acidic Functional Groups |
Phenol Carboxylic Acid Sulfonic Acid Sulfonamide (unless N is disubstituted) Oxazolindin (with two ketones only) Hydantoin Barbituric Acid |
| Water Soluble Functional Groups |
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 |
| Lipophilic Functional Groups |
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)
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| Not Stable In Vitro |
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)
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