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Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

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Page 1: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

Organic Chemistry- introduction 2 -

Vladimíra Kvasnicová

Page 2: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

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

Page 3: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

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

Page 4: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

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

Page 5: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

Aromatic compounds

• delocalization of π-elektrons

• more resonance structures

• planar molecules

• Hűckel rule: 4n + 2 = number of -electronsn = 1, 2, 3,...

Page 6: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

Aromatic hydrocarbons (= arenes)

= = = = benzene

= naphthalene=

= = anthracene

Page 7: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

= =

= phenanthrene

= = pyrene

= benzopyrene

Page 8: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

Hydrocarbon rests of arenes (aryls, Ar)

→ = = =

=

benzene

phenyl

= biphenyl

CH3

CH2

toluene benzyl

COOH

CO

benzoic acid

benzoyl

Page 9: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

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)

Page 10: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

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

Page 11: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

derivative

formula prefix suffix

carboxylic acid

- COOH carboxy- -oic acid

sulfonic acid

- SO3H sulfo- sulfonic acid

aldehyde - CHO formyl- -al

ketone C=O 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- -

Page 12: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

derivative

formula prefix suffix

carboxylic acid

- COOH carboxy- -oic acid

sulfonic acid

- SO3H sulfo- sulfonic acid

aldehyde - CHO formyl- -al

ketone C=O 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- -

Page 13: Organic Chemistry - introduction 2 - Vladimíra Kvasnicová

derivative

formula prefix suffix

carboxylic acid

- COOH carboxy- -oic acid

sulfonic acid

- SO3H sulfo- sulfonic acid

aldehyde - CHO formyl- -al

ketone C=O 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- -