All Classes of Organic Compounds

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1 Amines

2 All Classes of Organic Compounds ydrocarbons Functionalized ydrocarbons F,Cl,Br O,S, Alkanes Alkenes Alkynes Aromatics alides -O- -S- -- Alcohols Phenols Ethers Thiols Dissulfides Amines O C O C O C-O O C- Aldehydes Ketones Acids Esters Anhydrides Amides

3 Amines - Derivatives of Ammonia Classification by the number of attached groups ethylamine diethylamine triethylamine a primary amine a secondary amine a tertiary amine

4 Quartenary Ammonium Ions ammonium ion C 2 C 3 [ C 3 C 2 C 2 C 3 ] C 2 C 3 tetraethyl ammonium.. (part of a name) a quaternary ammonium salt

5 Cyclic Amines pyrrolidine pyrimidine imidazole purine

6 Amines - Classification Classification by the type of attached groups aromatic amines 2 2 aliphatic amines 3 C 2 C 2 3 C C 2 3 C

7 Amines - omenclature Amines containing simple groups are named with common nomenclature. Simple groups include: Unbranched alkyl groups: methyl, ethyl, propyl, butyl,., decyl Branched 3- and 4-carbon alkyl groups: isopropyl, isobutyl, s-butyl, t-butyl Unsubstituted cycloalkyl groups: cyclohexyl and cyclopentyl C3 C2 C3 ethylmethylamine C3 C C3 2º 1º isopropylamine C3 cyclohexylmethylamine C3 C3 2º 3º C2C3 ethyldimethylamine

8 Amines - omenclature C C 3 aniline 4-methyl aniline p-methyl aniline -methyl aniline

9 Amines - omenclature 2 C 2 C 2 C 2 COO 4-aminobutanoic acid C 3 C C 2 C 2 O 3 C C 3 3-(dimethylamino)-1-butanol C 3 C 3 C C C 2 C 3 C 3 3,-dimethyl-2-pentanamine

10 Worksheet on Amines

11 1. C3 C3 C C3 C2C2C3 amine 2. Br C3C2CC2CC3 C2C3-3-hexanamine 3. Br C2C2C3 -aniline

12 Amines - eterocyclic itrogen Compounds

13 Amines - Physical Properties 1º amine 2º amine 3º amine 1) Both 1º and 2º amines exhibit strong secondary forces (hydrogen bonding), primary amines slightly more so than secondary amines. 2) ydrogen bonding involving nitrogen atoms is weaker than that involving oxygen atoms because nitrogen is less electronegative than oxygen. a) The secondary forces in primary and secondary amines are weaker than those in alcohols. b) The strength of - hydrogen bonding in amines is comparable to the dipole-dipole forces in aldehydes and ketones.

14 Amines - Physical Properties 1º amine 2º amine 3º amine 1) Tertiary amines do not possess an - bond and therefore exhibit only weak secondary forces. 2) The strength of the weaker secondary forces in tertiary amines is comparable to those in ethers and hydrocarbons. 3) Tertiary amines have melting and boiling points considerably lower than those of primary and secondary amines, comparable to those of ethers and hydrocarbons.

15 Amines - Physical Properties

16 Amines - Physical Properties

17 Amines - Basic Compounds When dissolved in water, amines generate hydroxide ions O =, alkyl, aryl + + O- The product of the reaction is a salt and it is named from the name of the starting amine. C3 methylamine + 2O C3 + O- + a solution of methylammonium hydroxide

18 Acidities and Basicities of Organic Compounds Values for 0.10 M aqueous solution Compound Structure [O - ] [3O + ] p Ionization (%) sodium hydroxide ao 1.0 x x methyl amine C x x aniline C x x water 2O 1.0 x x ethanol C3C2O 1.0 x x phenol C65O 3.0 x x acetic acid C3COO 7.7 x x benzoic acid C65COO 4.0 x x hydrochloric acid Cl 1.0 x x

19 Amines - Basic Compounds Ammonia may be reacted with a strong acid to quantitatively yield an amonium salt. 3 + Cl 4Cl ammonia hydrogen ammonium chloride chloride An amine may be reacted with a strong acid to quantitatively yield an amine salt. C3 methylamine + Cl C3 Cl- + methylammonium chloride

20 Amines - Properties of Amine Salts C3 methylamine + Cl C3 + Cl- methylammonium chloride mp -94ºC, bp -6ºC mp 232ºC The melting and boiling points of amine salts are much higher than those of the corresponding amines. All amine salts are solids at room temperature. Amine salts are much more soluble in water than amines due to the strong interaction of water molecules with ions. Amines are soluble in neutral or lower p where they are converted into their salt forms.

21 Amines - Amine Based Drugs O C 2C2 C 3 Cl - + C3 Clphenylephrine hydrochloride EOSYEPIE 3-(2-(methylamino)ethyl)phenol hydrochloride O C 2 C 3 C O C 2C2 C 2 C 3 Cl C O C 2 C 2 C 3 Cl C 3 2 procaine hydrochloride OVACAIE 2-(diethylamino)ethyl 4-aminobenzoate hydrochloride diphenehydramine hydrochloride BEADYL 2-(benzhydryloxy)-,-dimethylethanamine hydrochloride

22 Biologically Interesting Amines

23 Biologically Interesting Amines

24 Interconversion of Amine Forms Cl Base Cl- + Cocaine (Free Base) Cocaine hydrochloride

25 Worksheet on Amines

26 4. C3 C3 C C3 C2C2C3 Cl isopropyl methyl propyl amine

27 5. C 3 C C 3 2 C 2 Cl ao C 3 dimethylpropyl ammonium chloride

28 6. C 3 C 2 C 3 C 2 C C 3 2 C 2 C 3 Cl ao

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