Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

inorganic compoundsorganic compounds high melting pointslow melting points most inorganic compounds are soluble in water most organic compounds are insoluble in water not soluble in organic liquidsare soluble in organic liquids most inorganic compounds conduct an electric current don´t conduct electricity met-et-prop-but-pent-hex-hept-oct-non-dec

Chemical properties hydrocarbons are hydrophobic (= lipophilic) because are nonpolar hydrocarbon derivatives: polar functional group + nonpolar tail reactivity:  multiple bonds  functional groups complete oxidation (= burning) of a hydrocarbon skeleton → CO 2 + H 2 O

Important chemical reactions of organic compounds 1.substitution (= replacement) CH 4 + Cl 2 → CH 3 Cl + HCl 2.addition (multiplicity of chemical bond is lowered) CH 2 =CH 2 + H 2 O → CH 3 -CH 2 -OH 3.elimination (new multiple bond is often formed, small molecule is released) CH 3 -CH 2 -OH → CH 2 =CH 2 + H 2 O 4.rearrangement (= formation of an isomer) CH 2 =C(OH)-COOH → CH 3 -C(O)-COOH

Aromatic compounds delocalization of π-elektrons more resonance structures planar molecules Hűckel rule: 4n + 2 = number of  -electrons n = 1, 2, 3,...

Aromatic hydrocarbons (= arenes) === = benzene = naphthalene = = = anthracene

== = phenanthrene = = pyrene = benzopyrene

Hydrocarbon rests of arenes (aryls, Ar) →=== = benzenephenyl = biphenyl → toluenebenzyl → benzoic acid benzoyl

Important derivatives of benzene methylbenzene = toluene dimethylbenzenes = xylenes (o-, m-, p-)  1,2-dimethylbenzene = o-xylene  1,3-dimethylbenzene = m-xylene  1,4-dimethylbenzene = p-xylene vinylbenzene = styrene ( → polystyrene, PS)

DERIVATIVES OF HYDROCARBONS principal functional group  type of the derivative  suffix other functional groups → expressed by special prefixes + locants The name of the compound is derived from the name of the basic unbranched hydrocarbon

derivativeformulaprefixsuffix carboxylic acid - COOH carboxy--oic acid sulfonic acid - SO 3 H sulfo-sulfonic acid aldehyde - CHO formyl--al ketone C=O oxo--one alcohol - OH hydroxy--ol thiol - SH mercapto--thiol amine - NH 2 amino--amine ether - O - R-oxy-ether sulfide - S - R-thio-sulfide halogen der. - F, -Cl, -Br, -I halogen-- nitro der. - NO 2 nitro--

derivativeformulaprefixsuffix carboxylic acid - COOH carboxy- -oic acid sulfonic acid - SO 3 H sulfo-sulfonic acid aldehyde - CHO formyl--al ketone C=O oxo--one alcohol - OH hydroxy- -ol thiol - SH mercapto--thiol amine - NH 2 amino--amine ether - O - R-oxy-ether sulfide - S - R-thio-sulfide halogen der. - F, -Cl, -Br, -I halogen-- nitro der. - NO 2 nitro--

derivativeformulaprefixsuffix carboxylic acid - COOH carboxy--oic acid sulfonic acid - SO 3 H sulfo-sulfonic acid aldehyde - CHO formyl--al ketone C=O oxo--one alcohol - OH hydroxy- -ol thiol - SH mercapto--thiol amine - NH 2 amino- -amine ether - O - R-oxy-ether sulfide - S - R-thio-sulfide halogen der. - F, -Cl, -Br, -I halogen-- nitro der. - NO 2 nitro--