Alkynes

Val Joseph de Guzman Marx Lennin Cabaltican

Hydrocarbons containing carbon-carbon triple covalent bonds are called ALKYNES.

Unsaturated hydrocarbons with a triple bond in the molecule, containing 2 atoms less than the corresponding saturated hydrocarbons, have the general formula CnH2n-2

 more unsaturated than alkenes thus they add two equivalents of bromine whereas an alkene adds only one equivalent more reactive than alkenes show greater tendency to polymerize or oligomerize than alkenes do

At usual temperature, the C2-C4 alkynes are gases, C5-C14 are liquids, and the superior ones are solids boiling points are similar, yet a bit higher than the alkanes and alkenes points solubility is higher than their corresponding saturated hydrocarbons

As with hydrocarbons in general, alkynes are non-polar and are insoluble in water but soluble in non-polar organic solvents.

In acetylene, the H-CC bond angles are 180. The CC bond distance of 121 picometers is much shorter than the C=C distance in alkenes (134 pm) or the C-C bond in alkanes (153 pm). The triple bond is very strong with a bond strength of 839 kJ/mol.

Nomenclature

Functional group suffix = -yne Disubstituted alkynes, R-CC-R', are described as "internal" alkynes Monosubstituted alkynes, R-CC-H, are described as "terminal" alkynes.

The first in naming an alkyne is to count the carbons in the longest carbon chain

prefix determined by the number of carbon atoms in the chain:

eth prop but pent hex C2 C3 C4 C5 C6 hept oct non dec C7 C8 C9 C10

Name ethyne

no. C atoms(n) 2

no. H atoms (2 x n) - 2 (2 x 2) - 2 = 2

Formula C2H2

Name propyne

no. C atoms(n)
3

no. H atoms (2 x n) - 2
(2 x 3) - 2 = 4

Formula C3H4

Name
1-butyne

no. C atoms(n)
4

no. H atoms (2 x n) - 2
(2 x 4) - 2 = 6

Formula C4H6

Name
1-pentyne

no. C atoms(n)
5

no. H atoms (2 x n) - 2
(2 x 5) - 2 = 8

Formula C5H8

Name
1-hexyne

no. C atoms(n)
6

no. H atoms (2 x n) - 2
(2 x 6) - 2 = 10

Formula C6H10

Name
1-heptyne

no. C atoms(n)
7

no. H atoms (2 x n) - 2
(2 x 7) - 2 = 12

Formula C7H12

Name
1-octyne

no. C atoms(n)
8

no. H atoms (2 x n) - 2
(2 x 8) - 2 = 14

Formula C8H14

Alkynes with two triple bonds are alkadiynes (diynes), ones with three carbon double bonds are alkatriynes (triynes), and so on.

A straightforward extension to the numbering system is used to properly name them. So, CCCC C is 1,3-pentadiyne 1,2,3-hexatriyne (CCCCCC).

Naming Branched Alkynes

1. First, find the longest carbon chain. This chain must contain the maximum number of double and triple bonds. This is the main chain used to determine the name.

2. Assign numbers to the carbons where the side groups exist.

3. If there is more than one multiple bond (double or triple) the numbering begins at the end closest to multiple bond positions are named first, whether it is a double or triple bond locations.

4. Give the side group carbon numbers and names first, then the location of the double bonds, followed by numbers of the triple bonds.

CH 3
CH3 C C CH CH

CH3
CH2

C H2 CH 3

CH 3
CH3 C C CH CH

CH3
CH2

C H2 CH 3

-yne

CH 3
CH3 C C CH CH

CH3
CH2

C H2 CH 3

-yne

CH 3
CH3
1

CH3
7

C
2

C
3

CH
4

CH

CH2
6

C H2 CH 3

-yne

methyl CH3

CH3
7

CH3
1

C
2

C
3

CH
4

CH

CH2
6

C H2 CH 3
ethyl

2-heptyne

methyl CH3

CH3
7

CH3
1

C
2

C
3

CH
4

CH

CH2
6

C H2 CH 3
ethyl

5-ethyl-4-methyl-2-heptyne

o acetylene was and still is one of the most used raw material of the of the organic chemistry industry o from acetylene you can obtain rubber, vinyl poly chloride and many more.

o Acetylene is used as an illuminant. o It is used for the production of oxyacetylene flame. The temperature of the flame is above 3000oC. Is is employed for cutting and welding of metals.

o Acetylene is used for artificial ripening of fruits. o Used in the preparation of several carbon compounds like acetaldehyde , acetic acid , ethyl alcohol , benzene etc .

o Used in the preparation of solvents westron ( acetylene tetrachloride ) westrol o ( trichloroethylene ) . o Used in Hawker's lamp and in light houses for illumination purposes .

end