Erica Jane L.

Sulit
Rhoyelle D. Mag-isa
 Hydrocarbons are the simplest organic compounds .
Containing only carbon and hydrogen, they can be
straight-chain, branched chain, or cyclic molecules.
Carbon tends to form four bonds in a tetrahedral
geometry. Hydrocarbon derivatives are formed when
there is a substitution of a functional group at one or
more of these positions.
 Alkanes – saturated hydrocarbons
(CnH2n+2)
Alkanes are hydrocarbons that contain only carbon-
carbon single bonds.
 Every carbon atom participates in 4 single bonds, either
to another carbon or to a hydrogen.
 Every hydrogen atom is bonded to a carbon by a single
bond.
Alkanes – saturated hydrocarbons (CnH2n+2)
Alkanes are hydrocarbons that contain only carbon-
carbon single bonds.
 Alkanes in which the carbons are connected in a straight
chain are called normal alkanes.

H H H H H H
n-hexane
H C C C C C C H
H H H H H H

 Alkanes that are branched are called branched chain

alkanes.
H
H C H
2-methyl-pentane
H H H H
H C C C C C H
H H H H H
Alkanes – saturated hydrocarbons
(CnH2n+2)

main natural source:

 natural gase
(up to 97% of methane; ethane, propane, CO2, N2)

 petroleum
(mixture of aliphatic, alicyclic, and polycyclic
hydrocarbons C1-C50; the composition varies with its
location)
Alkanes – saturated hydrocarbons
(CnH2n+2)

methane ethane hexane

3-methylpenthane

Alkanes are not planar !

 Alkanes – saturated hydrocarbons
(CnH2n+2)
physical properties:
 not soluble in water (= hydrophobic)

 non polar bonds (similar electronegativity of C and H)

 densities between 0.6 and 0.8 g/cm3 (= less than water)

 colorless, tasteless, nearly odorless

 boiling points increase with increasing MW, and decrease

with branching (C1-C4 are gases)
 volatility decreases with molar weight (MW)

 narcotic and irritant effects increase with MW (! C5-C9)

 Alkanes – saturated hydrocarbons
(CnH2n+2)
alkanes and the human body:
 inhalation of alkane vapors (e.g. gasoline)
causes severe damage to the lung tissue
(it dissolves cellular membranes)
 liquid alkanes can also harm the skin: long-term contact
between low MW alkanes and skin remove skin oils and
can cause soreness and blisters
 high MW alkanes can be used to protect the skin:
mixtures of C20-C30 alkanes are used in skin and hair
lotions to replace natural oils
 mineral oil purified mixture has been used as a laxative
 Constitutional Isomers
When two or more molecules share the same molecular
formula, but have different atomic connections, they
are called constitutional isomers.
H
H H H H H H
H C H
H C C C C C C H
H H H H
H H H H H H H
H C C C C C H
H H H H H H C H
n-hexane
H H H
3-methyl-pentane
H H H C C C C H
H C H H C H H H H

H H H H H H H
H C H
H C C C C C H H C C C C H
H
H H H H H H H H
2,3-dimethylbutane
2-methyl-pentane H C H
H
2,2-dimethylbutane
Alkenes, Alkynes & Aromatic
Compounds
The remaining three families of hydrocarbons are unsaturated.

 Alkanes are saturated, which means they contain the maximum

number of hydrogens per carbon.

• For alkanes CnH(2n+2)

 Alkenes, Alkynes and Aromatics are unsaturated, which means

they contain less than the maximum number of hydrogens per
carbon.

• Structurally, this means that they have carbon-carbon double or triple

bonds
Alkenes – unsaturated hydrocarbons
(CnH2n)
 Alkenes are hydrocarbons that contain at least 1
carbon-carbon double bond.
 Examples:

H H H H
C C C C
H H H CH2 CH2 CH2 CH3
ethene 1-hexene
(ethylene)
Alkenes – unsaturated hydrocarbons
(CnH2n)
physical properties:
 not soluble in water (= hydrophobic)

 nonpolar bonds (similar electronegativity of C and H)

 low boiling points – lower than alkanes of the same

length (C1-C4 are gases)
 double bond consist of 1 and 1 bond

 the double bond does not permit free rotation

geometric isomerism
Alkenes – unsaturated hydrocarbons
(CnH2n)
 ethene (= ethylene) is planar

http://www.chem.umass.edu/~rday/chem110/ethenepi.gif
Alkenes – unsaturated hydrocarbons
(CnH2n)
 example of geometric isomers:

http://www.gunthersclass.com/24_10.jpg
Alkenes – unsaturated hydrocarbons
(CnH2n)

 alkenes have higher biological efect than alkanes

 their narcotic efect and toxicity increase with MW

and with other unsaturated bonds
 2 double bonds: ALKADIENS

2-methyl-1,3-butadiene
= isoprene
Alkenes – unsaturated hydrocarbons
(CnH2n)
polymerization
 „polymers“ are high molecular weight molecules
made from thousands of repeating units, which
are low molecular weight molecules („monomers“)
 it is a multiple addition reaction of alkenes
e.g. n CH2=CH2 → (-CH2-CH2-)n

 properties of polymers depend on the monomer

used and MW of the product
 Alkynes – unsaturated hydrocarbons
(CnH2n-2)
 Alkynes are hydrocarbons that contain at least 1
carbon-carbon triple bond.
 Examples:

H C C H H C C CH2 CH2 CH2 CH3

ethyne 1-hexyne
(acetylene)
Alkynes – unsaturated hydrocarbons
(CnH2n-2)
physical properties:
 boiling points slightly higher than that of alkanes
and alkenes
 specific gravity higher in comparision to alkenes

 the triple bond = 1 and 2 bonds

 it is shorter than the double bond

 the reactivity of the triple bond is similar to that of

the double bond of alkenes (addition reactions)
 ethyne (= acetylene): all four atoms in a stright line
Aromatic hydrocarbons
 Aromatics are unsaturated ring molecules
 They are often drawn to look like alkenes, but they
behave much differently than alkenes.
 They have an alternating pattern of double and single
bonds within a ring.
 Benzene is an example
Aromatic hydrocarbons
benzene
 liquid of pleasant odour
 narcotic effect
 can damage the bone marrow
(it can give rise to leukemia)

toluene and xylenes

 narcotic and irritant effect
 less dangerous than benzene
Aromatic hydrocarbons
biphenyl
 suspected from cancerogenesis

naphtalene
 irritant effect (skin, mucosa)
 causes methemoglobinemia and the kidney damage

benzo(a)pyrenes
 cancerogenic effect
Important common (trivial) names
- add structural formulas -
 ethene = ethylene
 ethyne = acetylene
 trichloromethane = chloroform
 chloroethene = vinylchloride
 2-methylbut-1,3-diene = isoprene
 methylbenzene = toluene
 dimethylbenzenes = xylenes
 vinylbenzene = styrene
MEMORIZE THESE NAMES