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Running head: ALKYNES

ALKYNES

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Running head: ALKYNES

Background information.

Ethyne (acetylene) was first discovered in 1836 by Edmund Davy, an Irish Chemist. It is a by-

product in the preparation of metallic potassium by heating a mixture of calcinated potassium

titrate with charcoal. F. Wöhler synthesized ethyne by treating calcium carbide with water in

1862. Since Davy gave his observations only in his laboratory findings, the discovery of alkynes

was given credit to Wöhler. Bertherlot then synthesized ethyne from carbon and hydrogen in that

same year.

Theory.

i) Structures of alkynes

Alkynes are organic molecules made of the functional group carbon-carbon triple bond and their

empirical formula is written as CnH(2n-2). They are traditionally known as acetylenes or the

acetylene series, although acetylene also refers to the simplest member of the series called

ethyne. The alkynes are unsaturated hydrocarbons. They have the suffix –yne, this suffix is used

when there is only one alkyne in the molecule. The triple bond is made of one sigma bond and

two pi bonds. Alkynes are similar to alkenes in their ability to act as a nucleophile due to the

presence of the pi bonds. There are two types of alkynes: terminal alkynes that have a hydrogen

bonded to a carbon in the triple bond and internal alkynes that have non-hydrogen compound and

atom on both carbons having the triple bond.

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Figure 1. Internal alkyne. Figure 2. Terminal alkyne.

ii) Physical properties of alkynes

 All alkynes are odourless and colourless except for ethylene which has a slight distinctive

oduor.

 The first three alkynes (ethyne, propyne and butyne) are gases while the next eight are

liquids. All the other higher alkynes are solids.

 Alkynes are slightly polar in nature.

 Alkynes have low boiling and melting point. The boiling and melting point of alkynes

increases as their molecular structure grows bigger and molecular mass increases. The

boiling points of alkynes are slightly higher than the corresponding alkynes since they

have an extra bond at the carbon site.

 Alkynes are insoluble in water and soluble in organic solvents.

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iii) Chemical properties of alkynes

 Alkynes are slightly acidic in nature due the hydrogen atoms attached to the carbon-

carbon triple bond.

 Alkynes are generally very reactive except for ethyne, which are not commonly found.

 Reaction of alkynes are:

- Addition of dihydrogen.

The reaction occur in the presence of Nickel or Platinum or Palladium catalyst. In this reaction

hydrogen is added to alkyne to form alkene.

- Addition of halogens.

In the reaction of halogens such as and alkynes, the halogen adds itself to the structure of the

alkyne to form halogen substituted alkenes.

- Addition of water.

Alkynes do not react with water, but the reaction can occur when alkynes are bubbled through

dilute sulphuric acid in presence of mercuric sulphate catalyst giving carbonyl compounds as

products. This reaction is known as a hydration reaction.

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- Polymerization

Alkynes undergo cyclic and linear polymerization under suitable conditions. After

polymerization, the product compound has higher molecular formula than original alkyne.

Example, ethyne polymerize to form polyethene.

- Hydroboration oxidation

iv) Synthesis and occurrence of alkyne.

Alkyne are both naturally occurring and synthesized.

The naturally occurring acetylenes have been discovered from terpenes that is isolated from

variety of plants species, cultures of higher fungi. Therefore are obtained from fungi cultures,

plant sources.

Alkynes are also found in crude oil and natural gas, although they naturally in plants and in some

animals physiological functions.

Alkynes are generally synthesized by:

 Dehydrohalogenation of vicinal alkyl dihalides.

 The reaction of metal acetylides with primary alkyl halides.

 Preparing them from aldehydes.

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Applications of alkynes.

Alkynes are used in:

- Preparation of organic solvents.

- Preparation of polymers.

- Artificially ripening fruits as anesthetic for making poisonous mustard gas.

- Light portable lamps installed in cars, bicycles and house.

- Welding and for cutting material that require high temperatures.

- Production of polyethylene products.

- Manufacturing inorganic compound eg vitamins like vitamin A and E.

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- Alkynes called ene-dynes are used for antintumor compound.

- Manufacture drugs such antifungal terbinatine.

- Ethyne used as fuel for carbine lamps.

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References.

McMurry, John. Organic Chemistry. 6th ed. Belmont, CA: Brooks/Cole, 2004. ISBN

0534420052.

Morrison, Robert T., and Robert N. Boyd. Organic Chemistry. 6th ed. Englewood Cliffs, NJ:

Prentice Hall, 1992. ISBN 0-13-643669-2.

Solomons, T.W.Graham, and Fryhle, CraigB. Organic Chemistry. 8th ed. Hoboken, NJ: John

Wiley, 2004. ISBN 0471417998.