Al Kynes

Alkynes
The alkynes are the third homologous series of organic compounds of hydrogen and carbon, where there
is at least one triple-bond between the atoms in the molecules.
The alkenes are said to be unsaturated because of the existence of a multiple bond in the molecule. The
general structure of the alkene series of hydrocarbons is CnH2n-2. The first member of the ethene series
is ethyne (previously called acetylene). The names of all alkynes end in "-yne". Rules for the systematic
naming of alkynes are similar to those for alkenes. In the case of higher members of the alkene series,
the triple bond may be between the terminal carbon atoms of the chain, or may be between internal
carbon atoms in the chain.
Ethyne (Acetylene) HCCH

Propyne HCCCH3
1-Butyne HCCCH2CH3
1-Pentyne HCC(CH2)2CH3
1-Hexyne HCC(CH2)3CH3
1-Heptyne HCC(CH2)4CH3
1-Octyne HCC(CH2)5CH3
1-Nonyne HCC(CH2)6CH3
1-Decyne HCC(CH2)7CH3
2-Butyne CH3CCCH3
2-Pentyne CH3CCCH2CH3
The bond formed between the hydrogen atom and the unsaturated carbon atom, and first bond
between the unsaturated carbon atoms in the ethynes are s bonds (sigma bonds) and these bonds are
formed by the end-on overlap of sp hybrid orbitals of the carbon atoms and the bonds are arranged as
far apart in space as possible (i.e. at 180 degree) to form a linear molecule. The second and third bonds
that makes up the triple bond of the unsaturated carbon atoms in alkenes are p-bonds (pi-bonds),
formed by the side-on overlap of the two p-orbitals on each of the carbon atoms. The p-bonds (pi-
bonds) are much more reactive than the s bonds (sigma bonds), and react readily in addition reactions.
Acetylene is a linear molecule, all four atoms lying along a straight line. This linear structure can only be
explained by the existence of sp hybridisation of the orbitals of the carbon atoms of ethyne.
The carbon-carbon triple bond is thus made up of one strong bond and two weaker (bonds; it has a total
strength 123 kcal. It is stronger than the carbon-carbon double bond of ethylene 100 kcal or the single
carbon-carbon bond of ethane 83 kcal, and therefore is shorter than either.
The C-C distance is 1.2 A, as compared with 1.34 A in ethylene and 1.54 A in ethane and is a more
electronegative grouping than that formed by carbon atoms joined by either a double or a single bond.
The hydrogen attached to the carbon-carbon triple bond in ethyne or in any alkyne where the carbon-
carbon triple bond is situated at the end of a carbon chain is able to separate from the rest of the
molecule as a hydrogen ion; the electronegative carbon is able to retain both electrons from the broken
covalent bond.
A significant result of this bonding is that ethyne can unite with metals and so be distinguished from
alkenes by chemical means.
The linear structure does not permit geometric isomerism of ethyne.
Alkynes Physical Properties
https://www.ucc.ie/academic/chem/dolchem/html/dict/alkynes.html
http://study.com/academy/lesson/alkynes-properties-uses-formula-examples.html
https://www.cliffsnotes.com/study-guides/chemistry/organic-chemistry-i/alkynes/alkynes-nomenclature
https://chem.libretexts.org/Core/Organic_Chemistry/Alkynes/Naming_the_Alkynes
Alkynes are compounds which have low polarity, and have physical properties that are essentially the
same as those of the alkanes and alkenes.
They are insoluble in water.
They are quite soluble in the usual organic solvents of low polarity (e.g. ligroin, ether, benzene, carbon
tetrachloride, etc.).
They are less dense than water.
Their boiling points show the usual increase with increasing carbon number.
They are very nearly the same as the boiling points of alkanes or alkenes with the same carbon
skeletons.
Table of the physical properties of Alkynes
Name Formula MP degC BP degC Density(20C)
========= =========== ======= ======= ============
Acetylene HCCH -82 -75
Propyne HCCCH3 -101.5 -23
1-Butyne HCCCH2CH3 -122 91
1-Pentyne HCC(CH2)2CH3 -98 40 0.695
1-Hexyne HCC(CH2)3CH3 -124 72 0.719
1-Heptyne HCC(CH2)4CH3 -80 100 0.733
1-Octyne HCC(CH2)5CH3 -70 126 0.747
1-Nonyne HCC(CH2)6CH3 -65 151 0.763
1-Decyne HCC(CH2)7CH3 -35 182 0.770
2-Butyne CH3CCCH3 -24 27 0.694
2-Pentyne CH3CCCH2CH3 -101 55 0.714
Alkynes are identified as organic chemical compounds that have triple bonds in their chemical structure.
They are organic compounds that are important in various industrial applications. In this lesson, we will
learn all about alkynes.
What Are Alkynes?
There are so many different classifications of organic chemical compounds.
One of these are organic compounds called alkynes. What are alkynes and
how do we know that a chemical compound is an alkyne? Alkynes are
hydrocarbons, which are organic chemical compounds containing carbon (C)
and hydrogen (H) atoms, and the feature that makes them recognized as
alkynes is the presence of triple bonds.
Chemical compounds that have triple and double bonds in their chemical
structures are referred to as unsaturated. Because alkynes have triple bonds
in their chemical structure and consist of carbon and hydrogen atoms, they
are unsaturated hydrocarbons.
Below, we can see the general chemical structure of alkynes (RCCR'). The
carbon (C) atoms shown below are bonded together by a triple bond. We can
also see two side groups, R and R', which are bonded to the carbon (C)
atoms. The side groups R and R' could be any group that consist of hydrogen
and/or carbon atoms. An example of an alkyne is shown below, where the
there is a triple bond between two carbon (C) atoms and the side groups R is
-CH sub 2CH sub 3 and the R' is -CH sub 2CH sub 3.
General Formula of Alkynes and Example
Properties of Alkynes
What do alkynes physically look like? Are they usually solids, liquids, or
gases? In general, alkynes are in gaseous form and they are soluble in
organic solvents, like benzene and acetone. They are, however, insoluble in
water. Another property of an alkyne is that, if try to burn an it, the flame
results will turn out to be a sooty flame.
Let's compare the acidity and boiling point of alkynes to the other
hydrocarbons, alkenes (hydrocarbons that have double bonds) and alkanes
(hydrocarbons that are only made of single bonds).
Alkanes, Alkenes and Alkynes
In general, alkynes are more acidic than alkenes and alkanes, and the boiling
point of alkynes also tend to be slightly higher than alkenes and alkanes.
Alkynes: Acidity and Boiling Point

Compared to Alkanes and Alkenes
Alkynes: Uses and Examples
Alkynes have various industrial applications. Let's take a look at a few

examples of common alkynes and what they are used for.
Acetylene, also referred to as ethyne, is one of the most well-known and

widely used alkynes. Acetylene is very useful because it can undergo several
chemical reactions that are needed in manufacturing products in different
industries.
Let's think about plastic - we use plastic products for so many things, and
plastic is made using a compound called polyethylene. Acetylene is an
important raw material in the chemical industry to produce polyethyelene.
Have you ever heard of an acetylene torch? This type of torch is used to cut
weld and steel, and it uses acetylene as fuel.
Another alkyne, propyne, also known as methylacetylene, is commonly used

as a substitute for acetylene as fuel for welding torches. It is also being
investigated as possible fuel for rockets in space craft.
Examples of Alkynes
Alkynes: Nomenclature
Although some common alkyne names, such as acetylene, are still found in
many textbooks, the International Union of Pure and Applied Chemistry
(IUPAC) nomenclature is required for journal articles. The rules for alkynes in
this system are identical with those for alkenes, except for the ending. The
following rules summarize alkyne nomenclature.
1. Identify the longest continuous chain of carbon atoms that contains the
carboncarbon triple bond. The parent name of the alkyne comes from the
IUPAC name for the alkane of the same number of carbon atoms, except the
ane ending is changed to yne to signify the presence of a triple bond. Thus,
if the longest continuous chain of carbon atoms containing a triple bond has
five atoms, the compound is pentyne.
2. Number the carbon atoms of the longest continuous chain, starting at the
end closest to the triple bond. Thus, is numbered from right to left, placing
the triple bond between the second and third carbon atoms of the chain.
(Numbering the chain from left to right incorrectly places the triple bond
between the third and fourth carbons of the chain.)
3. The position of the triple bond is indicated by placing the lower of the pair
of numbers assigned to the triplebonded carbon atoms in front of the name
of the alkyne. Thus the compound shown in rule 2 is 2pentyne.
4. The location and name of any substituent atom or group is indicated. For
example, the compound is
5chloro2hexyne.
Nomenclature of Alkynes
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Alkynes are organic molecules made of the functional group carbon-carbon triple bonds and are written in
the empirical formula of CnH2n2CnH2n2. They are unsaturated hydrocarbons. Like alkenes have the
suffix ene, alkynes use the ending yne; this suffix is used when there is only one alkyne in the
molecule. If a molecule contains both a double and a triple bond, the carbon chain is numbered so that the
first multiple bond gets a lower number. If both bonds can be assigned the same number, the double bond
takes precedence. The molecule is then named "n-ene-n-yne", with the double bond root name preceding
the triple bond root name (e.g. 2-hepten-4-yne).
Introduction
Here are the molecular formulas and names of the first ten carbon straight chain alkynes.
Name Molecular Formula
Ethyne C2H2
Propyne C3H4
1-Butyne C4H6
1-Pentyne C5H8
1-Hexyne C6H10
1-Heptyne C7H12
1-Octyne C8H14
1-Nonyne C9H16
1-Decyne C10H18
The more commonly used name for ethyne is acetylene, which used industrially.
Naming Alkynes
Like previously mentioned, the IUPAC rules are used for the naming of alkynes.
Rule 1
Find the longest carbon chain that includes both carbons of the triple bond.
Rule 2
Number the longest chain starting at the end closest to the triple bond. A 1-alkyne is referred to as a
terminal alkyne and alkynes at any other position are called internal alkynes. For example:
4-chloro-6-diiodo-7-methyl-2-nonyne
Rule 3
After numbering the longest chain with the lowest number assigned to the alkyne, label each of the
substituents at its corresponding carbon. While writing out the name of the molecule, arrange the
substituents in alphabetical order. If there are more than one of the same substituent use the prefixes di,
tri, and tetra for two, three, and four substituents respectively. These prefixes are not taken into account
in the alphabetical order. For example:
2,2,10-triiodo-5-methyl-3-decyne
If there is an alcohol present in the molecule, number the longest chain starting at the end closest to it,
and follow the same rules. However, the suffix would be ynol, because the alcohol group takes priority
over the triple bond.
5- methyl-7-octyn-3-ol
When there are two triple bonds in the molecule, find the longest carbon chain including both the triple
bonds. Number the longest chain starting at the end closest to the triple bond that appears first. The
suffix that would be used to name this molecule would be diyne. For example:
4-methyl-1,5-octadiyne
Rule 4
Substituents containing a triple bond are called alkynyl. For example:
1-chloro-1-ethynyl-4-bromocyclohexane
Here is a table with a few of the alkynyl substituents:
Name Molecule
Ethynyl -C?CH
2- Propynyl -CH2C?CH
2-Butynyl -CH3C?CH2CH3
Rule 5
A molecule that contains both double and triple bonds is called an alkenyne. The chain can be numbered
starting with the end closest to the functional group that appears first. For example:
6-ethyl-3-methyl-1,4-nonenyne
Outside links
http://en.wikipedia.org/wiki/Alkyne
http://www.cem.msu.edu/~reusch/VirtualText/nomen1.htm
Reference
1. Vollhardt, Peter, and Neil E. Schore. Organic Chemistry: Structure and Function. 5th Edition. New
York: W. H. Freeman & Company, 2007.
Problems
Name or draw out the following molecules:
1. 4,4-dimethyl-2-pentyne
2. 4-Penten-1-yne
3. 1-ethyl-3-dimethylnonyne
4.
Contributors
A. Sheth and S. Sujit (UCD)

Jonathan Mooney (McGill University)
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Alkynes

Ethyne (Acetylene) HCCH

Alkynes Physical Properties

Name Formula MP degC BP degC Density(20C)

========= =========== ======= ======= ============

Acetylene HCCH -82 -75

Propyne HCCCH3 -101.5 -23

1-Butyne HCCCH2CH3 -122 91

1-Pentyne HCC(CH2)2CH3 -98 40 0.695

1-Hexyne HCC(CH2)3CH3 -124 72 0.719

1-Heptyne HCC(CH2)4CH3 -80 100 0.733

1-Octyne HCC(CH2)5CH3 -70 126 0.747

1-Nonyne HCC(CH2)6CH3 -65 151 0.763

1-Decyne HCC(CH2)7CH3 -35 182 0.770

2-Butyne CH3CCCH3 -24 27 0.694

2-Pentyne CH3CCCH2CH3 -101 55 0.714

What Are Alkynes?

Alkynes: Acidity and Boiling Point

Alkynes: Uses and Examples

Alkynes have various industrial applications. Let's take a look at a few

Acetylene, also referred to as ethyne, is one of the most well-known and

Another alkyne, propyne, also known as methylacetylene, is commonly used

Name Molecular Formula

Substituents containing a triple bond are called alkynyl. For example:

Here is a table with a few of the alkynyl substituents:

Name or draw out the following molecules:

A. Sheth and S. Sujit (UCD)

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