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

2. CH10 C 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 1s 2 2s 2 2p 2

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

4.  CH 4 (methane)  C 2 H 6 (ethane) C 2 H 6  C 3 H 8 (propane)  C 4 H 10 (butane)  C 5 H 12 (pentane)  C 6 H 14 (hexane)  C 7 H 16 (heptane)  C 8 H 18 (octane)  C 9 H 20 (nonane)  C 10 H 22 (decane)  C 11 H 24 (undecane)  C 12 H 26 (dodecane)  C 13 H 28 (tridecane)  C 14 H 30 (tetradecane) ALKANEs C n H 2n+2 CH10 CCCC C C

5.  C 2 H 4 (ethene) C 2 H 4  C 3 H 6 (propene)  C 4 H 8 (butene)  C 5 H 10 (pentene)  C 6 H 12 (hexene)  C 7 H 14 (heptene) ALKENEs C n H 2n CH10 C C C Nomenclature – position of double bond Nomenclature IUPAC is ethene, but common name ethylene (it is the same)IUPAC

6. ALKENES - reactions CH10 Breaking double bonds and substituting hydrogens, hydroxyl or halogen groups  Hydrogenation (adding H 2 ) – example production of margarine  Halogenation (adding halogens) – example halothane synthesis  Hydration (adding water HOH)  Polymerisation CH 2 =CH 2 +H 2 →CH 3 CH 3 ethene → ethane CH 2 =CH 2 +HOH→CH 3 CH 2 OH ethene → ethanol (ethyl alcohol)

7.  C 2 H 2 (ethyne) C 2 H 2  C 3 H 4 (propyne)  C 4 H 6 (butyne)  C 5 H 8 (pentyne)  C 6 H 10 (hexyne)  C 7 H 12 (heptyne) ALKYNEs C n H 2n-2 CH10 C C C H 43 2 H H H H 11 1-butyne C H CCC acetylene

8. Aromatic Hydrocarbons CH10 Ring structure with alternating single and double bonds C 6 H 6 (benzene), C 10 H 8 (naphthalene, two rings), C 14 H 10 (anthracene, three rings). benzene naphthalene H H H H H H C C C C C C H H H H C C C C H H H H C C C C C C Simplified symbols

9. Derivatives of Hydrocarbons CH10 One or more hydrogen atoms in hydrocarbons can be substituted by more reactive atoms (e.g., by halogens Cl, Br) H H H C Cl C F C F F F Methyl chloride Tetrafluoroethylene HH H Cl C C Ethylene chloride C 2 H 3 Cl (vinyl chloride)

10. Functional groups - R CH10 One or more hydrogen atoms in hydrocarbons can be substituted by functional group derived from alkanes -CH 3 (methyl), -C 2 H 5 (ethyl), -C 3 H 7 (propyl), or -OH (hydroxyl group /alcohols/), -COOH (carboxyl group /acids/), -NH 2 (amines), -CONH 2 (amides).

11. functional groups that enable the joining of two chains or other functional groups, -O- (ethers), -CO- (ketones, carbonyl group), -COO- (esters /fats/). Functional groups - R - CH10 - C – O - C – O - O Aldehyde (example formaldehyde H) Ketone (example aceton CH 3 COCH 3 ) Ketones have carbonyl group attached to carbons (this is the difference from aldehydes) esters are formed by condensing an acid with an alcoholcondensing

12. Functional groups isomers CH10 2-bromopropane 2,2,3 trimethylpentane C 8 H 18 Butane C 4 H 10 2 methylpropane C 4 H 10 CH 3 CHCH 3 Br CH 3 CH 3 CH 2 CH – C - CH 3 CH 3 CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 CHCH 3 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane C 8 H 18 ALKANES

13. Functional groups isomers CH10 CH 3 CH 2 CH=CH 2 1-butene CH 3 CH 2 CH=CH 2 Cl 2-chloro-1-butene CH 3 CH=C-CH 3 Cl 2-chloro-2-butene CH 3 CH 3 CH 2 -C  C-C-CH 3 CH 3 2,2-dimethyl-3-hexyne ALKENES and ALKYNES

14. Functional groups CH10 O H H H H H H C C 3 2 H H H H H H H 11 H H H C C CC H H H C Cl H H H O H C H H H C Methyl chloride Methyl 2-propane O H Methyl benzene- TOLUENE Methyl alcohol Ethyl alcohol Phenol ALCOHOLS H H H C C Ethyl benzene- STYRENE

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