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CH10
CHEMISTRY E182019
ORGANIC
CHEMISTRY
This course is approximately at this level
Rudolf Žitný, Ústav procesní a
zpracovatelské techniky ČVUT FS 2010
CH10
ORGANIC CHEMISTRY
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 CC chains of virtually unlimited extent.
Electronic structure
C
1s22s22p2
CH10
Hydrocarbons
pronuntiatio
n
ALKANES linear chains containing single bonds only (nontoxic, nonpolar
with low reactivity)
-C-C-….-C-
ALKENES linear chains containing at least one double bond (this bond
makes alkenes reactive)
-C=C-….-C-
ALKYNES linear chains containing at least one triple bond (extremely
reactive substances)
-CC-….-C-
AROMATIC HYDROCARBONS ring structure with alternating single
and double bonds
CH10
ALKANEs CnH2n+2
CH4
C2H6
C3H8
C4H10
C5H12
C6H14
C7H16
C8H18
C9H20
C10H22
C11H24
C12H26
C13H28
C14H30
(methane)
(ethane)
(propane)
(butane)
(pentane)
(hexane)
(heptane)
(octane)
(nonane)
(decane)
(undecane)
(dodecane)
(tridecane)
(tetradecane)
C
C C
C C C
CH10
ALKENEs CnH2n
C2H4
C3H6
C4H8
C5H10
C6H12
C7H14
(ethene)
(propene)
(butene)
(pentene)
(hexene)
(heptene)
C C C
Nomenclature IUPAC is ethene, but common name ethylene (it is the same)
Nomenclature – position of double bond
H
1
H
2
C
C
H
1-butene
H
H
3
4
C
C
H
H
H
1
H
H
H
2
C
H
2-butene
C
H
H
3
4
C
C
H
H
CH10
ALKENES - reactions
Breaking double bonds and substituting hydrogens, hydroxyl or halogen groups
Hydrogenation (adding H2) – example production of margarine
CH2=CH2+H2→CH3CH3 ethene → ethane
Halogenation (adding halogens) – example halothane synthesis
Hydration (adding water HOH)
CH2=CH2+HOH→CH3CH2OH ethene → ethanol (ethyl alcohol)
Polymerisation
CH10
ALKYNEs CnH2n-2
C2H2
C3H4
C4H6
C5H8
C6H10
C7H12
(ethyne)
(propyne)
(butyne)
(pentyne)
(hexyne)
(heptyne)
H
H
1
2
C
1-butyne
C
3
acetylene
C C C
H
4
C
C
H
H
H
CH10
Aromatic Hydrocarbons
Ring structure with alternating single and double bonds
C6H6 (benzene),
Simplified symbols
C10H8 (naphthalene, two rings),
C14H10 (anthracene, three rings).
H
C
H
H
naphthalene
H
H
H
H
C
C
H
C
C
C
C
C
C
C
C
C
C
C
H
H
benzene
H
C
C
H
H
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)
H
C
H
H
Cl
Methyl chloride
H
H
C
C
H
F
F
C
C
F
F
Tetrafluoroethylene
Cl
Ethylene chloride C2H3Cl (vinyl chloride)
CH10
Functional groups - R
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).
CH10
Functional groups - R -
functional groups that enable the joining of two chains or other functional groups,
-O- (ethers),
-CO- (ketones, carbonyl group),
-C–
O
-COO- (esters /fats/).
-C–O-
Aldehyde (example
formaldehyde H)
Ketone (example
aceton CH3COCH3)
O
esters are formed by condensing
an acid with an alcohol
Ketones have carbonyl group
attached to carbons (this is
the difference from
aldehydes)
Functional groups isomers
CH10
ALKANES
CH3CHCH3
2-bromopropane
Br
CH3CH2CH2CH2CH2CH2CH2CH3
Octane C8H18
CH3
CH3CH2 CH – C - CH3
2,2,3 trimethylpentane C8H18
CH3 CH3
CH3CH2CH2CH3
CH3CHCH3
CH3
Butane C4H10
2 methylpropane C4H10
CH10
Functional groups isomers
CH3CH2CH=CH2
1-butene
CH3CH2CH=CH2
2-chloro-1-butene
ALKENES and ALKYNES
Cl
CH3CH=C-CH3
2-chloro-2-butene
Cl
CH3
CH3CH2-CC-C-CH3
CH3
2,2-dimethyl-3-hexyne
CH10
Functional groups
ALCOHOLS
H
C
H
Methyl chloride
H
Cl
H
C
H
H
H
1
2
C
H
C
H
Methyl alcohol
H
3
C
H
H
Methyl 2-propane
H
C
H
H
H
H
H
H
C
H
Methyl benzeneTOLUENE
H
C C
H
H
O
H
O
O
H
Ethyl alcohol
H
H
Phenol
H
H
C C
H
Ethyl benzeneSTYRENE
Functional groups - R -
CH10
ACIDS
H
H
H
C
O
H
C
Acetic acid
H
N
H
R
O
C
C
H
O
H
Amino acid
O
O
H
Benzoic acid
C
H
O
H
H
H
H
C
C O
C
C H
H
H
H
H
H
H
C C
C
H
H
H
Methyl amine
N
H
Diethyl ether
H
O
C
H
H
H
H
H
Dimethyl ketone
H
H
C
C
H
H
O
O
H
C
C
H
H
Ethyl acetate