Review of Reactions covered in CHE 102:

Physical Properties of alkanes refer to 102 notes

Give the products for the following reactions:

Alkanes: Not as reactive as alkenes and alkynes

Combustion:

Halogenation: Substitution reaction

Exercise: Refer to last week’s additional problems

Mechanism: Free radical chain mechanism involving initiation, propagation and

termination steps. Refer to CHE 102 notes.

Cracking: Longer chains broken down to give small useful short chain alkanes.

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Alkenes and Alkynes

Alkenes and alkynes undergo addition reactions

Hydrogenation: Is a reduction reaction

Alkenes

Alkynes

Dissolving metal reduction

Halogenation

Mechanism: What is a mechanism? It is a step by step process which shows how

reactants are converted to products.

Predicting Reactivity of Organic compounds:

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Electron rich atoms or molecules are attracted to electron deficient atoms or
molecules.

Electrophile: Refers to electron deficient atoms or molecules e. g. H+ , CH3CH2+

Nucleophiles: Refers to electron rich atoms or molecules. E.g. H2O, Cl-, CH3NH2

Curved or Curly arrows

They represent simultaneous movement of 2 electrons from an electron rich

center to an electron poor center.

1. Draw a curly arrow so that it points in the direction of electron flow.

2. Curved arrows are meant to to indicate the movement of electrons. Never

use a curved arrow to indicate the movement of an atom.

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 3. A head of a curved arrow always points at an atom or at a bond. Never
draw an arrow head pointing out into space

4. The arrow always starts at an electron rich source, e.g. in the example
below the arrow starts at an electron rich  bond not a carbon atom.

Alkenes

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More examples

Alkynes

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Hydration

Alkenes

Symmetrical alkenes

Unsymmetrical Alkenes

Apply Markovnikov’s rule: The hydrogen adds to the carbon with more hydrogens

Alkynes
Symmetrical Alkynes

Unsymmetrical Alkynes

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Terminal alkynes: Less reactive therefore need more activation, hence the use of
HgSO4

Addition of alcohols (ROH) to alkenes

Alcohols react with alkenes in the presence of an acid catalyst to give ethers. The
mechanism for the reaction is similar to acid catalyzed hydration of alkenes, i.e.
Use ROH instead of HOH.

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Hydrohalogenation

Alkenes
Symmetrical alkenes

Unsymmetrical alkenes

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Regioselectivity is the preferential formation of one constitutional isomer over
another.
Products of addition of unsymmetric reagents to unsymmetric alkenes are called
regioisomers. Regiospecific additions give only one product, whereas
regioselective additions give mainly one isomer.
NB: The stability of carbocations is as follows: 3o 2o 1o

Symmetrical Alkynes

Unsymmetrical alkynes

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Hydrohalogenation in the presence of peroxides

Alkenes

Mechanism: Free radical chain mechanism, involving initiation, propagation and

termination steps.

NB: Stability of radical follows the order: 3o 2o 1o

Termination: Combination of any two radicals.

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Acidity of Terminal Alkynes

The H atom on a triply bonded C atom is weakly acidic and can be removed by a
very strong base, e.g. sodium amide. As the hybridization at C becomes more s-
like and less p-like the acidity of the attached H increases.

Acetylide ion reacts with primary alkyl halides (RX) and methyl halides (CH3X)
forming new C-C bonds.

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Exercise:

How would you synthesize each of the following compounds using acetylene
as the starting material.

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