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

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 a)alicyclic saturated - cycloalkanes → cyclo……ane (cyclopropane) b) alicyclic unsaturated – cycloalkenes and cycloalkadienes c) aromatic hydrocarbons = arens (benzene and its derivatives )

Hydrocarbon rests (alkyls, R) CH 4 → CH 3 - → -CH 2 - methanemethyl methylene CH 3 -CH 3 → CH 3 -CH 2 - → -CH 2 -CH 2 - ethane ethyl ethylene CH 2 =CH 2 → CH 2 =CH- → -CH=CH- ethenevinyl vinylene („ethylene“)(ethenyl)

Aromatic hydrocarbons benzene anthracene naphthalene

phenantrene pyrene

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 pyrrole pyridine pyrimidine purine indole imidazole OXYGEN in the cycle furane tetrahydrofurane pyrane tetrahydropyrane

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

derivativeformulaprefixsuffix carboxylic acid- COOHcarboxy--oic acid sulfonic acid- SO 3 Hsulfo-sulfonic acid aldehyde- CHOformyl--al ketone= COoxo--one alcohol- OHhydroxy--ol thiol- SHsulfanyl--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--

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“.

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)

ETHERS R 1 -O-R 2 (R = alkyl or aryl) Alkyl ether (ethyl methyl ether) ! alphabetic order ! or alkoxy + name of hydrocarbon (methoxyethane) i.e. diethyl ether (common name „ether“) SULFIDES R 1 -S-R 2 (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

KETONES R 1 -CO-R 2 (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-NH 2 Alkylamine (methylamine) b) secondary amines R 1 -NH-R 2 Alkyl 1 (alkyl 2 )amine e. g. ethyl(methyl)amine ! alphabetic order ! N-alkylhydrocarbonamine (N-methylethanamine) c) tertiary amines R 1 -NR 2 -R 3 Alkyl 1 (alkyl 2 )alkyl 3 amine (trimethylamine)

NITROCOMPOUNDS R-NO 2 Prefix: nitro- (nitromethane, nitrobenzene) SULFONIC ACIDS R-SO 3 H Hydrocarbonsulfonic acid (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

Derivatives of carboxylic acids 1.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 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(NH 2 )- COOH Prefix: amino- !!Trivial names of amino acids!! (glycine, alanine, leucine,..)

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 R 1 -O-CO-R 2 (R 1 - = alkyl from alcohol) suffix: -ate/-oate Full name: alkyl carboxylate (methyl acetate, ethyl ethanoate) 2.3. Anhydrides R 1 -CO-O-CO-R 2 Acid → anhydride (acetic acid → acetic anhydride)

2.4. Amides R-CO-NH 2 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)

Organic reactions Addition reactions: 2 or more molecules combine to form a larger one Hydration: addition of water i. e. fumarate + H 2 O → malate Hydrogenation: addition of H 2 usually to unsaturated organic compounds i.e. CH 2 =CH 2 + H 2 → CH 3 -CH 3 Unsaturated fatty acids (in oils) can be converted to solid fats (margarine) Halogen addition ● Elimination reactions: Dehydration = loss of H 2 O from reacting molecule i.e. conversion of alcohols to ethers 2 R-OH → R-O-R + H 2 O i.e. conversion of carboxylic acids to anhydrides 2 R-COOH → R-CO-O-CO-R + H 2 O

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 O 2 - )