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Rudolf Žitný, Ústav procesní a zpracovatelské techniky ČVUT FS 2010

This course is approximately at this level. CHEMISTRY E182019. CH10. ORGANIC CHEMISTRY. Rudolf Žitný, Ústav procesní a zpracovatelské techniky ČVUT FS 2010. ORGANIC CHEMISTRY. CH10.

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Rudolf Žitný, Ústav procesní a zpracovatelské techniky ČVUT FS 2010

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  1. This course is approximately at this level CHEMISTRYE182019 CH10 ORGANIC CHEMISTRY Rudolf Žitný, Ústav procesní a zpracovatelské techniky ČVUT FS 2010

  2. ORGANIC CHEMISTRY CH10 Carbon is the basis of every organic substance, and its prominent role follows from its capacity to make as many as four highly stable covalent bonds (including single, double and triple bonds), and due to its ability to form covalently linked C-C chains of virtually unlimited extent. Electronic structure 1s22s22p2 C

  3. Hydrocarbons CH10 pronuntiation • ALKANES linear chains containing single bonds only (nontoxic, nonpolar with low reactivity) • ALKENES linear chains containing at least one double bond (this bond makes alkenes reactive) • ALKYNES linear chains containing at least one triple bond (extremely reactive substances) • AROMATIC HYDROCARBONS ring structure with alternating single and double bonds -C-C-….-C- -C=C-….-C- -CC-….-C-

  4. C C C C C C ALKANEs CnH2n+2 CH10 • CH4 (methane) • C2H6 (ethane) • C3H8 (propane) • C4H10 (butane) • C5H12 (pentane) • C6H14 (hexane) • C7H16 (heptane) • C8H18 (octane) • C9H20 (nonane) • C10H22 (decane) • C11H24 (undecane) • C12H26 (dodecane) • C13H28 (tridecane) • C14H30 (tetradecane)

  5. C C C ALKENEsCnH2n CH10 • C2H4 (ethene) • C3H6 (propene) • C4H8 (butene) • C5H10 (pentene) • C6H12 (hexene) • C7H14 (heptene) Nomenclature IUPAC is ethene, but common name ethylene (it is the same) Nomenclature – position of double bond

  6. ALKENES - reactions CH10 • Breaking double bonds and substituting hydrogens, hydroxyl or halogen groups • Hydrogenation (adding H2) – example production of margarine • Halogenation (adding halogens) – example halothane synthesis • Hydration (adding water HOH) • Polymerisation CH2=CH2+H2→CH3CH3 ethene → ethane CH2=CH2+HOH→CH3CH2OH ethene → ethanol (ethyl alcohol)

  7. C H H H 3 4 1 1 2 C C C C H H H 1-butyne ALKYNEsCnH2n-2 CH10 • C2H2 (ethyne) • C3H4 (propyne) • C4H6 (butyne) • C5H8 (pentyne) • C6H10 (hexyne) • C7H12 (heptyne) acetylene C C

  8. H H H C C C H H H H C C C C C C C C C C H H H C C C H H H H Aromatic Hydrocarbons CH10 Ring structure with alternating single and double bonds C6H6 (benzene), C10H8 (naphthalene, two rings), C14H10 (anthracene, three rings). Simplified symbols naphthalene benzene

  9. H H H C C C Cl F F F F H H C C Cl H Derivatives of Hydrocarbons CH10 One or more hydrogen atoms in hydrocarbons can be substituted by more reactive atoms (e.g., by halogens Cl, Br) Methyl chloride Tetrafluoroethylene Ethylene chloride C2H3Cl (vinyl chloride)

  10. Functional groups- R CH10 One or more hydrogen atoms in hydrocarbons can be substituted by functional group derived from alkanes -CH3 (methyl), -C2H5 (ethyl), -C3H7 (propyl), or -OH (hydroxyl group /alcohols/), -COOH (carboxyl group /acids/), -NH2 (amines), -CONH2 (amides).

  11. C – • O • C – O - • O Functional groups - R - CH10 functional groups that enable the joining of two chains or other functional groups, -O- (ethers), -CO- (ketones, carbonyl group), -COO-(esters /fats/). Aldehyde (example formaldehyde H) Ketone (example aceton CH3COCH3) esters are formed by condensing an acid with an alcohol Ketones have carbonyl group attached to carbons (this is the difference from aldehydes)

  12. CH3CHCH3 Br CH3 CH3CH2 CH – C - CH3 CH3 CH3 CH3CHCH3 CH3 Functional groups isomers CH10 ALKANES 2-bromopropane Octane C8H18 CH3CH2CH2CH2CH2CH2CH2CH3 2,2,3 trimethylpentane C8H18 CH3CH2CH2CH3 Butane C4H10 2 methylpropane C4H10

  13. CH3CH2CH=CH2 Cl CH3CH=C-CH3 Cl CH3 CH3CH2-CC-C-CH3 CH3 Functional groups isomers CH10 ALKENES and ALKYNES 1-butene CH3CH2CH=CH2 2-chloro-1-butene 2-chloro-2-butene 2,2-dimethyl-3-hexyne

  14. H H H H H H C C C H H C C C C C O O O H H H H H H C C H H H H Cl C H H H H H H H H 1 1 2 3 H H H H Functional groups CH10 ALCOHOLS Methyl chloride Methyl alcohol Methyl 2-propane Ethyl alcohol Methyl benzene-TOLUENE Phenol Ethyl benzene-STYRENE

  15. H H H C C H H H C C C C H H H R O O O H H H H N O O O H N O H H H H H H O H H H C C C C C C O H H C H H C C C O H C H H H H H H H H H H Functional groups - R - CH10 ACIDS Amino acid Acetic acid Methyl amine Benzoic acid Diethyl ether Ethyl acetate Dimethyl ketone

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