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Naming Organic Compounds Vladimíra Kvasnicová Carbon skeleton of organic compounds methane ethane hexane 3-methylpenthane Organic compounds can be cyclic C6: many conformations in space (free rotation of C-C; the most stable at room temperature: CHAIR conformation) http://www.chemistry.nmsu.edu/studntres/c hem539/answers/chexane_chair.jpg http://cat.middlebury.edu/~che m/chemistry/students/williamso n/stewart/chairboat.jpg Substituents in cyclic hydrocarbons geometric isomerism = the same sequential arrangement of atoms but different arrangement in space trans = E- cis = Z- http://www.arthistoryclub.com/art_history/Geometric_isomerism Double bond cannot rotate example of geometric isomers: http://www.gunthersclass.com/24_10.jpg NAMING ORGANIC COMPOUNDS Important prefixes: 1 meth- 2 eth- 3 prop- 4 but- 5 pent- 6 hex- 7 hept- mono di tri tetra penta hexa hepta 8 9 10 11 12 13 20 oct- non- dec- octa nona deca undec dodec tridec icosa- Valence of elements in organic compounds • CARBON always tetravalent • NITROGEN trivalent • OXYGEN bivalent • SULPHUR bivalent • HYDROGEN monovalent • HALOGENS monovalent Types of bonds: 1) single (-ane) saturated hydrocarbons 2) double (-ene) or triple (-yne) unsaturated hydrocarbons 3) conjugated (planar cycle: arens) Hydrocarbon rests (alkyls, R) CH4 methane → CH3methyl → -CH2methylene CH3-CH3 ethane → CH3-CH2ethyl → -CH2-CH2ethylene CH2=CH2 → ethene CH2=CHvinyl → -CH=CHvinylene („ethylene“) (ethenyl) Aromatic hydrocarbons = = = = = benzene = naphthalene = = anthracene = = = = phenanthrene = pyrene = benzopyrene Hydrocarbon rests of arens (aryls, Ar) → = = = benzene phenyl = CH3 CH2 CO COOH → → toluene = biphenyl benzyl 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) Important heterocyclic compounds NITROGEN in the cycle OXYGEN in the cycle • pyrrole • furan • pyridine • tetrahydrofuran • pyrimidine • pyran • purine • tetrahydropyran • indole • imidazole DERIVATIVES OF HYDROCARBONS The name of the compound is derived from the name of the basic unbranched hydrocarbon • principal functional group type of the derivative suffix • other functional groups → expressed by special prefixes + locants derivative formula prefix suffix carboxylic - COOH acid sulfonic acid - SO3H carboxy- -oic acid sulfo- sulfonic acid aldehyde - CHO formyl- -al ketone = CO oxo- -one alcohol - OH hydroxy- -ol thiol - SH sulfanyl- -thiol amine - NH2 amino- -amine ether -O- R-oxy- ether sulfide -S- R-thio- sulfide halogen der. - F, -Cl, -Br, -I halogen- - nitro der. nitro- - - NO2 derivative formula prefix suffix carboxylic - COOH acid sulfonic acid - SO3H carboxy- -oic acid sulfo- sulfonic acid aldehyde - CHO formyl- -al ketone = CO oxo- -one alcohol - OH hydroxy- -ol thiol - SH sulfanyl- -thiol amine - NH2 amino- -amine ether -O- R-oxy- ether sulfide -S- R-thio- sulfide halogen der. - F, -Cl, -Br, -I halogen- - nitro der. nitro- - - NO2 derivative formula prefix suffix carboxylic - COOH acid sulfonic acid - SO3H carboxy- -oic acid sulfo- sulfonic acid aldehyde - CHO formyl- -al ketone = CO oxo- -one alcohol - OH hydroxy- -ol thiol - SH sulfanyl- -thiol amine - NH2 amino- -amine ether -O- R-oxy- ether sulfide -S- R-thio- sulfide halogen der. - F, -Cl, -Br, -I halogen- - nitro der. nitro- - - NO2 DERIVATIVES OF HYDROCARBONS The name of the compound is derived from the name of the basic unbranched hydrocarbon ALCOHOLS R―OH (R = alkyl) • suffix: -ol (ethanol) • suffix: -diol (ethane-1,2-diol, ethylene glycol) • alkyl + alcohol (ethyl alcohol) • primary, secondary, tertiary alcohols • monofunctional / polyfunctional alcohols THIOLS (MERCAPTANS) R―SH • suffix: -thiol (methanethiol) / -dithiol • alkyl mercaptan (methyl mercaptan) • alkyl hydrosulfide (methyl hydrosulfide) PHENOLS Ar―OH (Ar = aryl) • common (trivial) names (phenol, cresols) ETHERS R1―O―R2 (R = alkyl or aryl) • alkyl ether (ethyl methyl ether) • alkoxyhydrocarbon (methoxyethane) SULFIDES R1―S―R2 (R = alkyl or aryl) • alkyl sulfide (ethyl methyl sulfide) ALDEHYDES R―CHO (R = H, alkyl or aryl) • suffix: -al (methanal) • carboxylic acid (trivial name) + aldehyde (formic acid → formaldehyde) • cycloalkane carbaldehyde KETONES R1―CO―R2 (R = alkyl or aryl) • suffix: -one (propanone) • alkyl ketone (dimethyl ketone) • trivial names (acetone) • diketones derived from arens: -quinone AMINES - derived from ammonia: H(s) replaced by alkyl(s) • primary: R―NH2 * alkylamine (methylamine) * hydrocarbonamine (methanamine) • secondary: R1―NH―R2 * alkyl1(alkyl2)amine ethyl(methyl)amine * N-alkylhydrocarbonamine N-methylethanamine • tertiary: R1―NR2―R3 * alkyl1(alkyl2)alkyl3amine * alkyl1(alkyl2)hydrocarbonamine • quarternary ammonium base: 4 alkyls-N+ * (multiple)alkylammonium (= cation) e.g. tetramethylammonium-chloride CATION ANION --------------------------------------------------------------+ trivial names (aniline) AZO DYES Ar1―N═N―Ar2 • hydrocarbon(larger one)azohydrocarbon • azohydrocarbon (Ar1 = Ar2) (azobenzene) R―NO2 NITROCOMPOUNDS • prefix: nitro- (nitromethane) SULFONIC ACIDS R―SO3H • hydrocarbonsulfonic acid (benzenesulfonic a.) CARBOXYLIC ACIDS R―COOH • suffix: -oic / -dioic acid • trivial names! • saturated / unsaturated • mono-, di-, tri-carboxylic acids • alpha () / omega () carbon • - or n- fatty acids • acyl / anion The figure was adopted from: J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2nd edition, Thieme 2005 Derivatives of carboxylic acids 1. substitutional derivatives → substitution in the chain of an acid → no change in the carboxyl group 2. functional derivatives → functional (carboxyl) group is changed Derivatives of carboxylic acids 1. substitutional derivatives → substitution in the chain of an acid 1.1. HALOGEN DERIVATIVES R(X)―COOH • prefix: chloro-, bromo-, iodo-, fluoro1.2. HYDROXY DERIVATIVES • prefix: hydroxy• trivial names! R(OH)―COOH 1.3. OXO DERIVATIVES R― (C═O)―COOH • prefix: oxo- / keto• trivial names! 1.4. AMINO DERIVATIVES R(NH2)―COOH • prefix: amino• trivial names! 2. functional derivatives → functional (carboxyl) group is changed 2.1. SALTS R―COO- M+ (M+ = metal cation) • suffix: -ate / -oate • -ic → -ate / -oic → -oate • R―COO- = carboxylate (anion of c.a.) • full name: cation carboxylate (sodium acetate) 2.2. ESTERS R1―O―C(O)―R2 • suffix: -ate • R1―O― = rest of alcohol • R1 = alkyl • full name: alkyl carboxylate (methyl acetate) 2.3. ANHYDRIDES R1―C(O)―O―C(O)―R2 • acid → anhydride • (acetic acid → acetic anhydride) • organic, organic-inorganic 2.4. AMIDES R―C(O)―NH2 • suffix: -amide (ethanamide) • -ic or –oic acid → -amide (acetamide) • substituted –NH2 group: N-alkyl…amide 2.5. ACYLHALIDES R―C(O)―X X = halogen • acyl name + halide (acetyl chloride) 2.6. NITRILES R―CN • hydrocarbon + suffix: -nitrile (ethanenitrile) • alkyl cyanide (methyl cyanide) Important chemical reaction of organic compounds 1. substitution (= replacement) CH4 + Cl2 → CH3Cl + HCl 2. addition (multiplicity of chemical bond is lowered) CH2=CH2 + H2O → CH3-CH2-OH 3. elimination (new multiple bond is often formed, small molecule is released) CH3-CH2-OH → CH2=CH2 + H2O 4. rearrangement (= formation of an isomer) CH2=C(OH)-COOH → CH3-C(O)-COOH Important chemical reaction of organic compounds • oxidation: oxygenation, dehydrogenation • reduction: hydrogenation • hydration /dehydration • esterification / ester hydrolysis • dissociation of carboxylic acids • aldol condensation of two carbonyl compounds • condensation reaction (= two molecules combine to form larger molecule with elimination of a small molecule)