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Pavla Balínová

Pavla Balínová. Naming organic compounds. Valence of elements in organic compounds: C = always tetravalent N = trivalent O = bivalent S = bivalent H = monovalent Halogens = monovalent Classification of organic compounds: 1. Hydrocarbons 2. Derivatives of hydrocarbons.

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Pavla Balínová

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  1. Pavla Balínová Naming organic compounds

  2. Valence of elements in organic compounds: C = always tetravalent N = trivalent O = bivalent S = bivalent H = monovalent Halogens = monovalent Classification of organic compounds: 1. Hydrocarbons 2. Derivatives of hydrocarbons

  3. Hydrocarbons - overview 1) Aliphatic (acyclic)hydrocarbons a) saturated - alkanes→ ending: -ane(methane) b) unsaturated - alkenes → ending: -ene (ethene) - alkadienes → ending: -diene(butadiene) - alkynes → ending: -yne (ethyne) 2) Cyclic hydrocarbons • alicyclic saturated -cycloalkanes → cyclo……ane (cyclopropane) b) alicyclic unsaturated – cycloalkenes and cycloalkadienes c) aromatic hydrocarbons = arens (benzene and its derivatives)

  4. Hydrocarbon rests (alkyls, R) CH4→ CH3-→ -CH2- methane methylmethylene CH3-CH3→ CH3-CH2-→-CH2-CH2- ethane ethylethylene CH2=CH2→ CH2=CH- → -CH=CH- ethene vinylvinylene („ethylene“) (ethenyl)

  5. Aromatic hydrocarbons benzene naphthalene anthracene

  6. phenantrene pyrene

  7. 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)

  8. Important heterocyclic compounds NITROGEN in the cycle • pyrrole • pyridine • pyrimidine • purine • indole • imidazole OXYGEN in the cycle • furane • tetrahydrofurane • pyrane • tetrahydropyrane

  9. DERIVATIVES OF HYDROCARBONSThe 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

  10. Rules for naming of organic compounds ●To find the longest unbranched chain containing the most functional groups or to find the longest unbranched chain containing the most double bonds or to find the longest unbranched chain • The main functional groups, multiple bonds and the other substituents must obtain the lowest number locants as possible Main functional group is the group with the highest position in the „Table of functional groups“ ordering the groups according to their „nomenclature importance“.

  11. Derivatives of hydrocarbons ALCOHOLS R-OH (R = alkyl) Suffix: -ol (methanol, ethanol, …..) or alkyl + alcohol (ethyl alcohol) Suffix: -diol (ethane-1,2-diol) or glycol (ethylene glycol) Primary, secondary, tertiary alcohols PHENOLS Ar-OH (Ar = aryl) Common (trivial) names (phenol, pyrocatechol, resorcinol) THIOLS(MERCAPTANES) R-SH Suffix: -thiol (methanethiol) or Alkyl + mercaptan (methyl mercaptan)

  12. ETHERS R1-O-R2(R = alkyl or aryl) Alkyl ether (ethyl methyl ether) ! alphabetic order ! or alkoxy + name ofhydrocarbon (methoxyethane) • e. diethyl ether (common name „ether“) SULFIDESR1-S-R2(R = alkyl or aryl) Alkyl sulfide (ethyl methyl sulfide) ALDEHYDES R-CHO (R = H, alkyl or aryl) Suffix: -al (methanal, ethanal, propanal, …) ! Trivial name of corresponding carboxylic acid + aldehyde (formic acid → formaldehyde, acetic acid → acetaldehyde) Cycloalkane carbaldehyde

  13. KETONES R1-CO-R2(R = alkyl or aryl) Suffix: -one (propanone, butanone, ..) or alkyl +ketone (dimethyl ketone) ! Trivial names (acetone) ! Diketones derived from arens: -quinone (1,4-benzoquinone) AMINES are derived from ammonia: H(s) replaced by alkyl(s) a) primary amines R-NH2 Alkylamine (methylamine) b) secondary amines R1-NH-R2 Alkyl1(alkyl2)amine e. g. ethyl(methyl)amine ! alphabetic order ! N-alkylhydrocarbonamine (N-methylethanamine) c) tertiary amines R1-NR2-R3 Alkyl1(alkyl2)alkyl3amine (trimethylamine)

  14. NITROCOMPOUNDS R-NO2 Prefix: nitro- (nitromethane, nitrobenzene) SULFONIC ACIDS R-SO3H Hydrocarbonsulfonicacid (benzensulfonic acid) CARBOXYLIC ACIDS R-COOH Suffix: -oic / -dioic acid !!!Trivial names!!! Saturated and unsaturated carboxylic acids Mono-, di-, tri-carboxylic acids Alpha α, beta β…….. carbon Acyl / anion

  15. Derivatives of carboxylic acids • Substitutional derivatives → substitution in the chain of an acid 1.1. Halogen derivatives R(X)-COOH X = halogen (Cl, Br,..) Prefix: chloro-, bromo-, iodo-, fluoro- 1.2. Hydroxy derivatives R(OH)-COOH Prefix: hydroxy- !!Trivial names!! (lactic acid,malic acid, citric acid) 1.3. Oxo derivatives R(C=O)-COOH Prefix: oxo- / keto- !!Trivial names!! (pyruvic acid) 1.4. Amino derivatives R(NH2)- COOH Prefix: amino- !!Trivial names of amino acids!! (glycine, alanine, leucine, ..)

  16. 2. Functional derivatives of carboxylic acids →functional (carboxyl) group is changed 2.1. Salts R-COO-M+ (M+ = metal cation) Suffix: -ate / -oate -ic → -ate / -oic → -oate R-COO- = anion of carboxylic acid Full name: cation carboxylate (sodium acetate) 2.2. Esters R1-O-CO-R2(R1- = alkyl from alcohol) suffix: -ate/-oate Full name: alkyl carboxylate (methyl acetate, ethyl ethanoate) 2.3. AnhydridesR1-CO-O-CO-R2 Acid → anhydride (acetic acid → acetic anhydride)

  17. 2.4. Amides R-CO-NH2 Suffix: -amide (ethanamide) -ic or –oic acid → -amide (formamide, acetamide) 2.5. Acylhalides R-CO-X (X = halogen) Acyl name + halide (acetyl chloride) 2.6. Nitriles R-CΞN Hydrocarbon + suffix: -nitrile (ethanenitrile /acetonitrile) Alkyl cyanide (methyl cyanide)

  18. Organic reactions • Addition reactions: 2 or more molecules combine to form a larger one Hydration: addition of water i. e. fumarate + H2O → malate Hydrogenation: addition of H2 usually to unsaturated organic compounds • e. CH2=CH2 + H2 → CH3-CH3 Unsaturated fatty acids (in oils) can be converted to solid fats (margarine) Halogen addition ● Elimination reactions: Dehydration = loss of H2O from reacting molecule i.e. conversion of alcohols to ethers 2 R-OH → R-O-R + H2O i.e. conversion of carboxylic acids to anhydrides 2 R-COOH → R-CO-O-CO-R + H2O

  19. Substitution reactions – a functional group in a particular compound is replaced by another group i.e. carboxylic acids → chlorides, amides of carboxylic acids • Rearrangement reactions – position of functional group is rearranged to give a structural isomer of the original molecule i.e. citrate → isocitrate ●Redox reactions: many redox reactions in organic chemistry have coupling mechanism involving free radicals intermediates (peroxides, superoxides O2-)

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