Isomerism and Reaction of Hydrocarbon PDF

ISOMERISM
structural and stereoisomerism

Look at the following structures!
CH3—CH2—CH2—CH3 CH3—CH—CH3
│
CH3
n-butane 2-methylpropane
(isobutane)
Similarities? differences?
ISOMERISM of Hydrocarbon compounds
Isomer is molecules
that have the same
molecular formula,
but have a different
structure or different
arrangement of the
atoms in space.
Structural Isomerism
1. Chain
example:
Structural Isomerism
2. Position Isomerism
it is the position of the functional group that varies in each isomer.
(for alkene and alkyne--movement of (═) and (≡))
example:
CH3 − CH2 − CH2 − CH ═ CH2 CH3 − CH2 − CH ═ CH2 − CH3

1-pentene 2-pentene
Stereoisomerism
1. Geometry
Cis-2-butene Trans-2-butene
Stereoisomerism
2. Optical (Chiral)
occurs when there is an asymmetric carbon (C has 4 different
atom or group attached).
(a) (b)
(a) The molecule and its mirror image are superimposable (achiral)
(b) The molecule and its mirror image are not superimposable
(chiral)
Example The mirror image
mirror
Two molecules with optical isomer sometimes reffered to as enantiomers.

Is the following molecule chiral?
Br CH3 CH2 −CH3

ǀ ǀ
│ CH3 −CH−CH−C−CH3
I—C —CH2 —CH3 ǀ ǀ
CH2 CH3
│ ǀ
Br CH3
Properties of Hydrocarbon
Boiling
Physical point
Chemical
Chemical reaction
Physical Properties of Hydrocarbon
Alkane, alkene, alkyne
• Melting point and boiling point increase when the molecular size
increases.
• Less dense than water.
• Insoluble in water but soluble in organic solvent.
• Colorless
• Can’t conduct electricity
• C1-C4 = gas
RiinSandrayanti/IBCSHS/2019 13
Physical Properties of Alkane, Alkene, &
Alkyne
• Boiling point
increase with molecular size.
Alkane b.p (°C) Alkene b.p (°C) Alkyne b.p (°C)

Ethane -89 Ethene -104 Ethyne -84
increases
Propane -42 Propene -47 Propyne -23

Butane 0.5 Butene -7 Butyne 8
Pentane 36 Pentene 30 Pentyne 40
Explanation
• Van der waals dispersion forces (in this

case London force) get bigger when the Boiling point 36°C
molecular size increases.
• The more branched the chain, the lower
the boiling point tends to be.
• Van der Waals dispersion forces are
smaller for shorter molecules (smaller
surface area).
Boiling point 9.5°C

Boiling point trend
alkyne alkane alkene
Decreases
Why alkynes has the highest b.p?

Some factors affected Van Der Waals forces
(LDF)
1. Molecular mass (Mr)
2. Shape of the molecules (surface area)
3. Bond length (pm) Alkane Alkene Alkyne
154 147 137
4. Electron Density
Alkyne has the highest boiling point than
others with the same number of carbon,
because:
• Triple bonds are the shortest. (137 pm). Correlation

between bond length and bond strength; shorter the bond
the stronger it is.
• It has branching limit that makes the surface area bigger.
Alkenes has lower boiling point than alkanes
with the same number of carbon because:
• The only attractions involved is Van der Waals

dispersion forces, and these depend on the C2H6
shape of the molecule and the number of
electrons it contains.
• Each alkene has 2 fewer electrons than the

C2H4
alkane with the same number of carbons so the
electron density is decreased. The higher the
electron density, the stronger the LDF. C2H2
Why Alkyne has higher boiling point than
others if alkyne has the least electron density
than alkane in the molecule with equal number
of carbon?
• Because the effect of branching and the attractive

force between carbon atom in alkynes is more
effective than electron density.
Chemical properties of Alkane,
Alkene, & Alkyne
1. In general alkane have a low reactivity, the most important

reaction are combustion (reaction with oxygen) and substitution
(halogenation).
2. Alkene and alkyne are more reactive than alkane.
3. The most characteristic reaction of alkene and alkyne is addition
and elimination. RiinSandrayanti/IBCSHS/2019 21
General Reaction of Alkane, alkene, and
alkyne
1. Combustion –(reaction with oxygen)

• In this reaction, CO2, H2O, and heat (energy) are
produced.
example:
CH4 + 2O2 → CO2 + 2H2O + energy
C2H4 + ...O2 →
Combustion
Complete combustion
• If its burnt in plenty of oxygen
• Produce CO2 and H2O
Incomplete combustion
• If its burnt in limitted supply of oxygen
• Produces CO and H2O
turns cloudy
Turns red
2. Substitution reaction
(halogenation)
• A substitution reaction occurs when one hydrogen atom is replaced by
another atom or group of atoms.
• Halogenation means one H atom replace by halogen (Cl, Br, or I).
• Often require heat and/or a catalyst in order to occur.
• Alkanes react with chlorine and bromine if we heat the mixture or if we
expose the mixture to light (in the dark at room temperature, nothing
happens).
If chloromethane is allowed to react with
more chlorine
Reaction of Alkene and Alkyne
•Addition is a reaction in which two molecules join together to make a bigger
one.
There are 4 types of addition :
1. Addition of hydrogen (hydrogenation)
2. Addition of water (hydration)
3. Addition of hydrogen halide (hydrohalogenation)
4. Addition of chlorine and bromine (halogenation)
1. Addition of hydrogen (Hydrogenation)
• A catalyst as platinum (Pt), Nickel (Ni), or palladium (Pd) is added to speed up
the reaction.
• Hydrogen and alkene are passed over a finely divided nickel catalyst at 140°C.
• Alkene → alkane
• Alkyne → alkene → alkane
Example
Ni
HC≡C—CH3 + H2
2. Addition of steam (Hydration)
• Use in the manufacture of ethanol-important chemical and solvent.
• A catalyst of immobilized phosphoric (V) acid (the acid is absorbed on a silica pellets).
330°C
6 MPa
Steam
3. Addition of hydrogen halide
(Hydrohalogenation)
• Hydrogen halide (HX ex: HCl, HBr, HI)
H H H Cl
ǀ ǀ ǀ ǀ
C═C + H−Cl →H−C−C−H
ǀ ǀ ǀ ǀ
H H H H
Markonikov’s rule
• …the more electronegative (for example negative ion) atom will predominantly bond
to the carbon atom of the double bond that has fewer hydrogen atoms.
Example
4. Addition of halogen-Halogenation
(Cl2, Br2, I2)
• No catalyst needed
• Can react at room temperature
• Use dichloromethane as a solvent
Elimination Reaction
• Is a method for preparation of alkenes by :
1. Dehydration from alcohols
2. Dehydrohalogenation of alkyl halides or halogenoalkanes
(hydrocarbon compound that contain halide, Cl, Br, or I)
Zaytzeff’s Rule
• If more than one elimination product is possible, the most
substituted alkane is the major product (most stable).
1. Dehydration from alcohol (water is produced)
Alcohols can undergo elimination via the loss of water.
This is known as dehydration.
H H
ǀ ǀ Acid, heat
H − C − C −H H2C = CH2 + H2O
ǀ ǀ
H OH
2. Dehydrohalogenation (halide (Cl-, Br-, I-) is
produced)
• Strong base like KOH (alcoholic) is used.
KOH(alc)
KBr

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ISOMERISM

structural and stereoisomerism

CH3 − CH2 − CH2 − CH ═ CH2 CH3 − CH2 − CH ═ CH2 − CH3

Two molecules with optical isomer sometimes reffered to as enantiomers.

Br CH3 CH2 −CH3

Alkane b.p (°C) Alkene b.p (°C) Alkyne b.p (°C)

Propane -42 Propene -47 Propyne -23

• Van der waals dispersion forces (in this

Boiling point 9.5°C

alkyne alkane alkene

Why alkynes has the highest b.p?

• Triple bonds are the shortest. (137 pm). Correlation

• The only attractions involved is Van der Waals

• Each alkene has 2 fewer electrons than the

• Because the effect of branching and the attractive

1. In general alkane have a low reactivity, the most important

1. Combustion –(reaction with oxygen)

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