Transcript Organic Chemistry

Organic Chemistry
- introduction -
Vladimíra Kvasnicová
Composition of Matter
• inorganic mater





• organic mater
oxygen (O)
50%
silicon (Si)
25%
aluminium (Al) 7%
iron (Fe)
5%
calcium (Ca)
3%
90%





sodium (Na)
potassium (K)
magnesium (Mg)
hydrogen (H)
titanium (Ti) 0,6%
„compounds of carbon“
C, O, H, N






carbon (C)
oxygen (O)
hydrogen (H)
nitrogen (N)
phosphorus (P)
sulfur (S)
Organic compounds
• „compounds of carbon“
• hydrocarbon skeleton: C, H
(linear / branched / cyclic)
 saturated: CH3-(CH2)n-CH3
 unsaturated: -CH=CH- or –C=C-
• heteroatoms: O, N, S, halogens
 heterocyclic compounds
 hydrocarbon derivatives (in functional groups)
• aliphatic or aromatic compounds
Valence of elements in organic compounds
• CARBON
always tetravalent
• NITROGEN
trivalent
• OXYGEN
bivalent
• SULPHUR
bivalent
• HYDROGEN
monovalent
• HALOGENS
monovalent
Types of bonds:
1) single (-ane)  saturated hydrocarbons
2) double (-ene) or triple (-yne)
 unsaturated hydrocarbons
3) conjugated (planar cycle: arens)
Shape of molecules
σ-bond
C-C
π-bond
C=C
C≡C
Alkanes
– hybridization sp3 – tetrahedral
shape
(4  bonds)
ethane
Alkenes
– hybridization sp2 – trigon (3  and 1 )
Alkynes
ethene
– hybridization sp – linear (2  and 2 )
ethyne
met-
et-
1
2
prop- but- pent- hex- hept- oct- non- dec3
4
5
inorganic compounds
6
7
8
9
organic compounds
high melting points
low melting points
most inorganic compounds are
soluble in water
most organic compounds are
insoluble in water
not soluble in organic liquids
are soluble in organic liquids
most inorganic compounds conduct
an electric current
don´t conduct electricity
10
Chemical properties
• hydrocarbons are hydrophobic (= lipophilic)
because are nonpolar
• hydrocarbon derivatives:
polar functional group + nonpolar tail
• reactivity:
 multiple bonds
 functional groups
• complete oxidation (= burning) of a hydrocarbon
skeleton → CO2 + H2O
Important chemical reactions of organic
compounds
1. substitution (= replacement)
CH4 + Cl2 → CH3Cl + HCl
2. addition (multiplicity of chemical bond is lowered)
CH2=CH2 + H2O → CH3-CH2-OH
3. elimination (new multiple bond is often formed,
small molecule is released)
CH3-CH2-OH → CH2=CH2 + H2O
4. rearrangement (= formation of an isomer)
CH2=C(OH)-COOH → CH3-C(O)-COOH
Hydrocarbon rests (alkyls, R)
CH4
methane
CH3methyl
→
-CH2methylene
CH3-CH3 →
ethane
CH3-CH2ethyl
→
-CH2-CH2ethylene
CH2=CH2 →
ethene
CH2=CHvinyl
→
-CH=CHvinylene
(„ethylene“)
(ethenyl)
→
Aromatic compounds
• delocalization of π-elektrons
• more resonance structures
• planar molecules
• Hűckel rule:
n = 1, 2, 3,...
4n + 2 = number of -electrons
Aromatic hydrocarbons (= arenes)
=
=
=
= benzene
= naphthalene
=
=
= anthracene
=
=
=
=
phenanthrene
=
pyrene
=
benzopyrene
Hydrocarbon rests of arenes (aryls, Ar)
→
=
=
=
benzene
phenyl
= biphenyl
=
CH3
CH2
→
→
toluene
CO
COOH
benzyl
benzoic acid
benzoyl
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)
Exercise
- add names of the compounds:
1.
CH3-CH2-CH2-CH3
2. CH3-CH2-CH=CH-CH3
3. CH2=CH2
4. CH3-CH2-CH2-CH2-C=CH
5. CH3-(CH2)10-CH3
butane
pent-2-ene
ethene
hex-1-yne
dodecane
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
Number of carbons / number of multiple
bonds or functional groups
1
2
meth- eth-
3
prop-
mono
di
tri
8
9
10
oct-
non-
dec-
octa
nona
deca
4
but-
5
pent-
tetra penta
11
12
6
7
hex- hepthexa
hepta
13
20
undec dodec tridec
icosa-
derivative
formula
prefix
suffix
carboxylic
- COOH
acid
sulfonic acid - SO3H
carboxy-
-oic acid
sulfo-
sulfonic acid
aldehyde
- CHO
formyl-
-al
ketone
= CO
oxo-
-one
alcohol
- OH
hydroxy-
-ol
thiol
- SH
mercapto-
-thiol
amine
- NH2
amino-
-amine
ether
-O-
R-oxy-
ether
sulfide
-S-
R-thio-
sulfide
halogen der. - F, -Cl, -Br, -I
halogen-
-
nitro der.
nitro-
-
- NO2
derivative
formula
prefix
suffix
carboxylic
- COOH
acid
sulfonic acid - SO3H
carboxy-
-oic acid
sulfo-
sulfonic acid
aldehyde
- CHO
formyl-
-al
ketone
= CO
oxo-
-one
alcohol
- OH
hydroxy- -ol
thiol
- SH
mercapto-
-thiol
amine
- NH2
amino-
-amine
ether
-O-
R-oxy-
ether
sulfide
-S-
R-thio-
sulfide
halogen der. - F, -Cl, -Br, -I
halogen-
-
nitro der.
nitro-
-
- NO2
derivative
formula
prefix
suffix
carboxylic
- COOH
acid
sulfonic acid - SO3H
carboxy-
-oic acid
sulfo-
sulfonic acid
aldehyde
- CHO
formyl-
-al
ketone
= CO
oxo-
-one
alcohol
- OH
hydroxy-
-ol
thiol
- SH
mercapto-
-thiol
amine
- NH2
amino-
-amine
ether
-O-
R-oxy-
ether
sulfide
-S-
R-thio-
sulfide
halogen der. - F, -Cl, -Br, -I
halogen-
-
nitro der.
nitro-
-
- NO2