• lower b.p. (b/c NH not as polarized as OH = not as good H-bond donors)
• high solubility; solubilize 5-6 Cs (b/c lone pair on N = excellent H-bond acceptor)
• basic (b/c lone pair); can be affected by steric effect (3⁰ is less basic than 2⁰), also groups that ↑ electron density of N ↑ basicity (and vice versa) > both balance so 2⁰ is more basic than 1⁰ and 3⁰ 
•  aryl amines less basic than cycloalkyl b/c resonance 
• basicity allows to make SALT with acid (charged = soluble) "aminium salts"

• naming: suffix "oic acid" replaces "e" from ane/ene

PROPERTIES

• much higher b.p. (b/c strong intermolecular H-bonding)
• OH group is much more polarized (than alcohol=better H-bond acceptor)
• ↑ water solubility (b/c H-bonding and ionization of O-H) 
• H is acidic b/c can delocalize neg. charge through resonance (not strong acid for same reason)

• reduction: to aldehyde
• with alcohol in acidic conditions : ester (OH replaced by OR from alcohol)
• with amine in acidic conditions : amide (OH replaced with amine)
• conjugation w/ glucuronic acid
• forms amide bond w/ glycine and glutamine
• beta-oxidation (metabolism of fatty acids)  

Esters

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• naming: alcohol hydrocarbon = substituent w/ "yl" suffix, space, then acid name "ic" replaced by "oate" 

PROPERTIES

• non-polar (eventhough made of 2 polar groups)
• ↓ b.p. (b/c lose H-bonding; from OH to OR)
• ↓ solubility (b/c no longer H-bond donor)
• neutral 
• unstable drugs, but good prodrugs (active form is acid or alcohol)
• very sweet smelling = use in food/cosmetic industry 

• hydrolized

1. oxidized in basic cond: OH replaces OR
2. reduced in acidic conditions: OH replaces OR

• esterase: break into carboxylic acid and alcohol (metabolism)

Amides

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• naming: amine hydrocarbon named 1st suffix "yl", space, acid name "oic" replaced wiht "amide"
• primary, secondary, tertiary = # C's attached

• higer b.p. (than ester) b/c can still H-bond
• ↑ H-bonding b/c resonance 
• N carry + charge = 3° amide form dipole-dipole = keep ↑ b.p. even though no H-bonding
• ↑ water solubility (b/c dipoles from resonance)
• lone pair not available for basicity b/c used in resonance = neutral
• stable (resist hydrolysis)

• metabolized by amidase to give carboxilic acid and amine

Lactones and Lactams

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• cyclic esters and amides
• same properties as linear forms 

• diester derivative of carbonic acid 

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• naming: determine the constituting alcohols names. 2 named as substitutents ending "yl" based on priority/alphabitical. 3. add "carbonate" at end
• properties parallel ester

• ester-amide derivative of carbonic acid

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•  naming: 1. determine names of alcohol and amine. 2 alcohol named as substituent ending "yl" followed by amine parent ending "yl". 3  completed by adding word "carbamate". 
• properties are combo of esters and amides

• diamide derivatives of carbonic acid

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• naming: 1 determine names of constituting amines. 2 name as substituents suffix "yl" based on priority/alphabetical. 3 follow by "urea"
• properties same as amides
• reactivity: more stable to hydrolysis

Oxole (furan)

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• O can be VERY basic (b/c electrons in sp² orbital)
• typically unreactive
• behaves like benzene; will undergo hydroxylation
• THF (tetrahydrofuran) is highly soluble in water, will undergo peroxidation in air

Thiole (Thiolphene)

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• relatively stable 
• Tetrahydrothiophene unilke ethers is fairly stable, also less water soluble 

Azole (pyrrole)

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• aromatic 
• week base = neutral (pyrrolidine is basic and fairly water soluble)

• O is part of ring = 2 extra pi electrons
• N is part of ring = 2 extra pi electrons
• aka ring normaly not aromatic can be (Huckel rule 4n+2 pi electrons)

oxirane (epoxides) and Aziridine 

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• reactions: oxiranes freely open (catalyzed by acid or base) 
• azetidine, add =O to corner get beta-Lactam; opened by hydrolysis or beta-lactamase

• basic (eventhough aromatic) b/c electrons on N not involved in resonancce
• isomer of isozazole

• resonance stabilizes 
• is aromatic w/ one basic N (can't tell which N b/c resonance)

6 membered heterocyles

with N and O

• slightly basic b/c lone pair from NH available to accept H
• if more O's than more electron withdrawling =  NH more willing to give up H than accept one
• Keto-Enol Tautomerism; keto = weak acid, enol = weak acid and base 
• saturated rings: similar properties to cyclic amine/ethers and cooresponding 2° amines and ethers

• 6 + 5 membered N heterocycles w/o benzene
• intramolecular interactions and Tautomerism(id guanine is keto form cannot have intramolecular bonds)
• intramolecular bonds change properties

with N are basic and behave like alkyl amines

important in medicinal chemistry

1. Acids

2. Anhydrides

3. Esters

4. Acid halides

5. Amides

6. Hydrazides

7. Imides

8. Nitriles

9. Aldehydes, followed by thioaldehydes

10. Ketones

11. Alcohols and Phenols

12. Hydroperoxides

13. Amines

14. Imines

15. Hydrazines, phosphanes

16. Ethers

17. Peroxides