organic chemistry - introduction - vladimíra kvasnicová
TRANSCRIPT
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Organic Chemistry- introduction -
Vladimíra Kvasnicová
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Composition of Matter
• inorganic 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%
• organic mater„compounds of carbon“
C, O, H, N
carbon (C) oxygen (O) hydrogen (H) nitrogen (N) phosphorus (P) sulfur (S)
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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
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Valence of elements in organic compounds
• CARBON always tetravalent
• NITROGEN trivalent
• OXYGEN bivalent
• SULPHUR bivalent
• HYDROGEN monovalent
• HALOGENS monovalent
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Types of bonds:
1) single (-ane) saturated hydrocarbons
2) double (-ene) or triple (-yne)
unsaturated hydrocarbons
3) conjugated (planar cycle: arens)
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Shape of molecules
σ-bond C-C
π-bond C=CC≡C
Alkanes– hybridization sp3 – tetrahedral
shape (4 bonds)
ethane
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Alkenes– hybridization sp2 – trigon (3 and 1 )
Alkynes– hybridization sp – linear (2 and 2 )
ethene
ethyne
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inorganic compounds 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
met- et- prop- but- pent- hex-
hept- oct- non- dec-
1 2 3 4 5 6 7 8 9 10
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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
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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
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Hydrocarbon rests (alkyls, R)
CH4 → CH3- → -CH2-
methane methyl methylene
CH3-CH3 → CH3-CH2- → -CH2-CH2-
ethane ethyl ethylene
CH2=CH2 → CH2=CH- → -CH=CH-
ethene vinyl vinylene(„ethylene“) (ethenyl)
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Aromatic compounds
• delocalization of π-elektrons
• more resonance structures
• planar molecules
• Hűckel rule: 4n + 2 = number of -electronsn = 1, 2, 3,...
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Aromatic hydrocarbons (= arenes)
= = = = benzene
= naphthalene=
= = anthracene
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= =
= phenanthrene
= = pyrene
= benzopyrene
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Hydrocarbon rests of arenes (aryls, Ar)
→ = = =
=
benzene
phenyl
= biphenyl
CH3
→
CH2
toluene benzyl
COOH
→
CO
benzoic acid
benzoyl
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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)
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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
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DERIVATIVES OF HYDROCARBONS
• principal functional group
type of the derivative suffix
• other functional groups
→ expressed by special prefixes +
locants
The name of the compound is derived from the name of the basic unbranched
hydrocarbon
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1 2 3 4 5 6 7
meth-
eth-prop
-but- pent- hex- hept-
mono
di tri tetrapent
ahexa
hepta
8 9 10 11 12 13 20
oct- non- dec-unde
c-dode
c-tride
c-icosa
-
octa nona deca
Number of carbons / number of multiple bonds or functional
groups
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derivative
formula prefix suffix
carboxylic acid
- COOH carboxy- -oic acid
sulfonic acid
- SO3H 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. - NO2 nitro- -
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derivative
formula prefix suffix
carboxylic acid
- COOH carboxy- -oic acid
sulfonic acid
- SO3H 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. - NO2 nitro- -
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derivative
formula prefix suffix
carboxylic acid
- COOH carboxy- -oic acid
sulfonic acid
- SO3H sulfo- sulfonic acid
aldehyde - CHO formyl- -al
ketone = CO oxo- -one
alcohol - OH hydroxy- -olthiol - 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. - NO2 nitro- -