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 Chemical Properties

Combustion of Alkynes
Ethyne burn in air with a luminous, smoky flame, (forming carbon dioxide and
water).

2 C2H2 + 5 02 ==> 4 CO2 + 2 H2O

The ethynes are highly dangerously explosives when mixed with air or
oxygen.
Oxidation of Alkynes
Ethyne is oxidised by a dilute aqueous solution of potassium permanganate to
form oxalic acid. Thus, if ethyne is bubbled through a solution of potassium
permanganate the solution is decolourised. This is Baeyer's test for unsaturated
organic compounds.

KMnO4

HCCH ==> O = COH

Ethyne O = COH

Oxalic Acid
Addition Reactions of Alkynes
Because of the unsaturated nature of ethyne addition reactions can occur across
the triple bond.
Addition of Hydrogen
When acetylene and hydrogen are passed over a nickel catalyst at 150 degC, (or
over platinum black catalyst at room temperature) ethene is first formed and
then this is further reduced to ethane.

Ni

150degC

HCCH + H2 ===>

Ethyne

Ni

150degC

H2C=CH2 + H2 ===> C2H6

Ethene Ethane
Addition of Halogens
Ethyne reacts explosively with chlorine at room temperature, forming hydrogen
chloride and carbon. To control the reaction, acetylene and chlorine (also
bromine) are added in retorts filled with kieselguhr (hydrated silica) and iron
filings.

HCCH + Cl2 ==> ClHC=CHCl + Cl2 ==> Cl2HCCHCl2

Addition of Hydrogen Halides.

Ethyne reacts with the halogen acids. Hydrogen iodide adding on the most
readily, at room temperature. A similar reaction occur with hydrogen bromide
at 100 degC. Reaction with hydrogen chloride occurs very slowly.

HCCH + HCl ==> H2C=CHCl + HCl ==> CH3CHCl2

Addition of Water (Hydration)

Hydration of ethyne occurs when the gas is passed into dilute sulphuric acid at
60 degC. Mercuric sulphate is used as a catalyst for the reaction, and the
product formed is ethanal (i.e. acetaldehyde).

HgSO4

60 degC

HCCH + H2O ==> CH3CHO

 Nitrile Formation
When a slight excess of ethyne and ammonia are passed over an alumina
catalyst at 573 degK, ethanonitrile (i.e. acetonitrile) is produced.

573 degK

HCCH + NH3 ==> CH3CN + H2

Ethyne Ethanonitrile

Polymerisation of Alkynes due to Triple Bond

The products obtained by polymerising ethyne depend on the conditions used.

When ethyne is passed through a glass tube at 4000C a little benzene is formed.
This is not a suitable way to make benzene in quantity but it is an example of
direct conversion from an open chain to an aromatic compound, (i.e. one with a
closed-ring benzenoid structure)

400 degC

3 C2H2 ==> C6H6

Ethyne Benzene

Two molecules of ethyne can be combined to produce vinyl ethyne,

HC(CCH=CH2, by passing the ethyne into a saturated solution of cuprous
chloride in ammonium chloride continuously in such a way that low
conversions of starting material occur.

Cu2Cl2

NH4Cl

2 HC CH ==> HCCCH = CH2

Ethyne Vinyl Ethyne

This linear polymerisation can be extended by altering the conditions of

reaction. For example,

HCCCH=CH2 + HCCH ==> CH2=CHC(CCH=CH2

 Vinyl Ethyne Ethyne DiVinyl Ethyne
Substitution Reaction of Alkynes
The reactions of ethynes indicate acidic properties for the hydrogens which are
attached to the carbon atoms involved in the triple bond. Ethynes readily form
compounds with metal.

When ethyne is passed through a solution of sodium in liquid ammonia then

sodium acetylide is formed and hydrogen is liberated.

liq.NH3

HCCH + 2Na ==> 2HCCNa + H2

Sodium

Acetylide

The other hydrogen atom in ethyne can be similarly replaced. When ethyne is
passed into a solution of cuprous chloride in ammonia, cuprous acetylide is
produced.

HCCH + Cu2Cl2 + NH4OH ==> CuCCCu

Copper

Acetylide

Silver acetylide is formed when ethyne is passed into an ammoniacal solution

of silver nitrate.

AgNO3

NH4OH

HCCH ==> AgCCAg + 2 HNO3

Silver

Acetylide
 These substitution reactions which ethynes undergo to form compounds with
metals are not occur with the alkenes. These reactions can be used as tests to
distinguish between acetylene and ethylene. When acetylene is passed through
an ammonical solution of silver nitrate or cuprous chloride, at room
temperature, precipitates of silver acetylide (white) or cuprous acetylide (red)
are formed.

In addition to distinguishing ethyne from ethene by chemical means, these

reactions provide a useful method for the preparation of higher alkynes:

HCC-Na+ + CH3I ==> HCCCH3 + NaI

Propyne

Warning : Methyl acetylides are explosive when dry so great care should be
taken in their preparation. The metal acetylides can be destroyed when they are
still wet by warming with dilute acid which will regenerate the parent ethyne.

HCC-Na(+) + HNO3 ==> HCCH + NaNO3

Alkynes Physical Properties

Alkynes are compounds which have low polarity, and have physical properties that
are essentially the same as those of the alkanes and alkenes.

1. They are insoluble in water.

2. They are quite soluble in the usual organic solvents of low polarity (e.g. ligroin,
ether, benzene, carbon tetrachloride, etc.).
3. They are less dense than water.
4. Their boiling points show the usual increase with increasing carbon number.
5. 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 Preparation
The carbon-carbon triple bond of the alkynes is formed in the same way as a double
bond of the alkenes, by the elimination of atoms or groups from two adjacent carbons.

W X W X
HC - CH ==> HC = CH ==> HCCH
X X
Alkane Alkene Alkyne
The groups that are eliminated and the reagents used are essentially the same as in the
preparations of alkenes.
Dehydrohalogenation of Alkyl Dihalides
This reaction is particularly useful since the dihalides are readily obtained from
the corresponding alkenes by addition of halogen. This amounts to conversion
by several steps of a double bond into a triple bond.

Dehydrohalogenation can be carried out in two stages. The halides thus

obtained, with halogen attached directly to double bonded carbon, are called
vinyl halides, and are very unreactive. Under mild conditions, therefore,
dehydrohalogenation stops at the vinyl halide stage; more vigorous conditions,
use of stronger base is required for alkyne formation. If only the first step of
this reaction is carried out, it is a valuable method for preparing unsaturated
halides.

Reaction of Sodium Acetylides with Primary Alkyl Halides

 This reaction permits conversion of smaller alkynes into larger ones. In
practice, the reaction is limited to the use of primary halides because of the
great tendency for secondary and tertiary halides to undergo a side reaction,
elimination.

NaNH2

HCCH ==> HCC(-)Na(+) + RX

Dehalogenation of Tetrahalides
This reaction is severely limited by the fact that these halides are themselves
generally prepared from the alkynes. As is the case with the double bond and a
dihalide, the triple bond may be protected by conversion into a tetrahalide with
subsequent regeneration of the triple bond by treatment with zinc.

Alkynes Reactivity
The unsaturated nature of alkynes means that most of their reactions will be similar to
those of alkenes (i.e. electrophilic addition), because of the availability of the loosely
held pi-electrons. The carbon to carbon triple bond is less reactive than the carbon to
carbon double bond towards electrophilic reagents. As well as the addition reactions,
alkynes undergo reactions that are due to the acidity of a hydrogen atom attached to
the triple bonded carbon.

The carbon-carbon triple bond in ethyne is thus made up of one strong sigma-bond
and two weaker pi-bonds. It has a total strength 123 kcal/mole. This is stronger than
the carbon-carbon double bond of ethylene which has a total strength of 100
kcal/mole or the single carbon-carbon bond of ethane which has a total strength of 83
kcal/mole.

The carbon-carbon bond lengths, which depend on the strengths of the bonds are

Ethyne CHCH 1.20 Angstrom Units

Ethylene CH2CH2 1.34 Angstrom Units

Ethane CH3CH3 1.54 Angstrom Units.

The ethynyl radical, CHC*, is a more electronegative group than that formed by
carbon atoms joined by either a double or a single bond. Thus, 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, so that the alkyne shows acidic properties. The
electronegative carbon is able to retain both electrons from the broken covalent bond.
A significant result of this bonding is that ethyne can form compounds with metals
and so be distinguished from alkenes by chemical means.

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 ALKYNES

H ydrocarbons that contain acarboncarbontriple bond are calledalkynes. Noncyclic alkynes have the
molecular formula CnH2n 2.Acetylene (HCPCH) is the simplest alkyne. We call compounds that have their triple
bond at the end of a carbon chain (RCPCH)monosubstituted, orterminal, alkynes. Disubstituted alkynes (RCPCR )
are said to haveinternal triple bonds. You will see in this chapter that a car-boncarbontriple bond is a functional
group, reacting with many of the same reagents
that react with the double bonds of alkenes.
The most distinctive aspect of the chemistry of acetylene and terminal alkynes is their acidity. As a class,
compounds of the type RCPCH are the most acidic of all simple hydrocarbons. The structural reasons for this property,
as well as the ways in which it is used to advantage in chemical synthesis, are important elements of this chapter.

9.1SOURCES OF ALKYNES
Acetylene was rst characterized by the French chemist P. E. M. Berthelot in 1862 and did not command much
attention until its large-scalepreparation from calcium carbide in the last decade of the nineteenth century stimulated
interest in industrial applications. In the rst stage of that synthesis, limestone and coke, a material rich in elemental
carbon obtained from coal, are heated in an electric furnace to form calcium carbide.
18002100C
CaO 3C CaC2 CO
Calcium oxide Carbon Calcium carbide Carbon monoxide
(from limestone) (from coke)

Calcium carbide is the calcium salt of the doubly negative carbide ion ( CPC ). Carbide dianion is strongly basic
and reacts with water to form acetylene:
339

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 340 CHAPTER NINE Alkynes
C 2
Ca2 2H2O Ca(OH)2 HCPCH
C
Calcium carbideWater Calcium hydroxide Acetylene

PROBLEM 9.1 Use curved arrows to show how calcium carbide reacts with water to give acetylene.

Beginning in the middle of the twentieth century, alternative methods of acetylene production became practical.
One of these is based on the dehydrogenation of ethylene.
heat
CH2CH2 HCPCH H2
Ethylene Acetylene Hydrogen

The reaction is endothermic, and the equilibrium favors ethylene at low temperatures but shifts to favor acetylene
above 1150C. Indeed, at very high temperatures most hydrocarbons, even methane, are converted to acetylene.
Acetylene has value not only by itself but is also the starting material from which higher alkynes are prepared.
Natural products that contain carboncarbontriple bonds are numerous. Two examples aretariric acid, from the
seed fat of a Guatemalan plant, andcicutoxin, a poisonous substance isolated from water hemlock.
O
X
CH3(CH2)10CPC(CH2)4COH
Tariric acid
HOCH2CH2CH2CPCCPCCHCHCHCHCHCHCHCH2CH2CH3
W
OH
Cicutoxin
Diacetylene (HCPCCPCH) has been identied as a component of the hydro-carbon-richatmospheres of
Uranus, Neptune, and Pluto. It is also present in the atmospheres of Titan and Triton, satellites of Saturn and Neptune,
respectively.

9.2NOMENCLATURE
In naming alkynes the usual IUPAC rules for hydrocarbons are followed, and the sufx -ane is replaced by-yne. Both
acetylene and ethyne are acceptable IUPAC names for HCPCH. The position of the triple bond along the chain is
specied by number in a manner analogous to alkene nomenclature.
HCPCCH3 HCPCCH2CH3 CH3CPCCH3 (CH3)3CCPCCH3
Propyne 1-Butyne 2-Butyne 4,4-Dimethyl-2-pentyne

PROBLEM 9.2 Write structural formulas and give the IUPAC names for all the alkynes of molecular formula C 5H8.

When the CPCH group is named as a substituent, it is designated as anethynyl group.

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 9.4Structure and Bonding in Alkynes: sp Hybridization 341
9.3PHYSICAL PROPERTIES OF ALKYNES
Alkynes resemble alkanes and alkenes in their physical properties. They share with these other hydrocarbons the
properties of low density and low water-solubility.They are slightly more polar and generally have slightly higher
boiling points than the corresponding alkanes and alkenes.

9.4STRUCTURE AND BONDING IN ALKYNES: sp HYBRIDIZATION

Acetylene is linear, with a carboncarbonbond distance of 120 pm andcarbonhydro-gen bond distances of 106 pm.

106 pm 106 pm
120 pm
HC CH
180 180

Linear geometries characterize the HCPCC and CCPCC units of terminal and internal triple bonds,
respectively as well. This linear geometry is responsible for the relatively small number of knowncycloalkynes. Figure
9.1 shows a molecular model for cyclononyne in which the bending of the CCPCC unit is clearly evident. Angle
strain destabilizes cycloalkynes to the extent that cyclononyne is the smallest one that is stable enough to be stored
for long periods. The next smaller one, cyclooctyne, has been isolated, but is relatively reactive and polymerizes on
standing.
In spite of the fact that few cycloalkynes occur naturally, they gained recent attention when it was discovered
that some of them hold promise as anticancer drugs. (See the boxed essay Natural and Designed Enediyne
Antibiotics following this section.)
An sp hybridization model for thecarboncarbontriple bond was developed in Section 1.18 and is reviewed for
acetylene in Figure 9.2. Figure 9.3 maps the electrostatic potential in ethylene and acetylene and shows how the second
bond in acetylene causes a band of high electron density to encircle the molecule.
Examples of physical properties of alkynes are given in Appendix 1.
FIGURE 9.1 Molecular model of cyclononyne, showing bending of bond angles associated with triply bonded carbons.
This model represents the structure obtained when the strain energy is minimized according to molecular mechanics and
closely matches the structure determined experimentally. Notice too the degree to which the staggering of bonds on adjacent
atoms governs the overall shape of the ring.
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 342CHAPTER NINE Alkynes
(a) (b) (c)

FIGURE 9.2 The carbon atoms of acetylene are connected by a triple bond. Both carbon atoms aresp-hybridized,and each is
bonded to a hydrogen by ansp1s bond. The component of the triple bond arises byspsp overlap. Each carbon has
twop orbitals, the axes of which are perpendicular to each other. One bond is formed by overlap of thep orbitals shown in (b),
the other by overlap of thep orbitals shown in (c). Each bond contains two electrons.
FIGURE 9.3 Electro-
static potential maps of eth-
ylene and acetylene. The re-
gion of highest negative
charge (red) is associated
with the bonds and lies be-
tween the two carbons in
both. This electron-richre-
gion is above and below the
plane of the molecule in eth-
ylene. Because acetylene has
two bonds, its band of high
electron density encircles the Ethylene Acetylene
molecule.
Back Forward
At this point, its useful to compare some structural features of alkanes, alkenes, and alkynes. Table 9.1 gives
some of the most fundamental ones. To summarize, as we progress through the series in the order
ethane ethylene acetylene:
1.The geometry at carbon changes from tetrahedral trigonal planar linear.
2.The CC and CH bonds become shorter and stronger.
3.The acidity of the CH bonds increases.
All of these trends can be accommodated by the orbital hybridization model. The bond angles are characteristic for
the sp3,sp2, andsp hybridization states of carbon and dont require additional comment. The bond distances, bond
strengths, and acidities are related to thes character in the orbitals used for bonding.s Character is a simple concept,
being nothing more than the percentage of the hybrid orbital contributed by ans orbital. Thus, ansp3 orbital has one
quarters character and three quartersp, ansp2 orbital has one thirds and two thirdsp, and ansp orbital one halfs and one
halfp. We then use this information to analyze how various qualities of the hybrid orbital reect those of
itss andp contributors.
Take CH bond distance and bond strength, for example. Recalling that an electron in a 2s orbital is, on average,
closer to the nucleus and more strongly held than an
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 9.4 Structure and Bonding in Alkynes:sp Hybridization343

TABLE 9.1 Structural Features of Ethane, Ethylene, and Acetylene

Feature Ethane Ethylene Acetylene

Systematic name Ethane Ethene Ethyne

Molecular formula C2H6 C2H4 C2H2

H H HH H
Structural formula C CC C H C C H
H
H HH H
CC bond distance, pm 153 134 120
CH bond distance, pm 111 110 106
HCC bond angles 111.0 121.4 180
CC bond dissociation energy, kJ/mol (kcal/mol) 368 (88) 611 (146) 820 (196)
CH bond dissociation energy, kJ/mol (kcal/mol) 410 (98) 452 (108) 536 (128)
Hybridization of carbon sp3 sp2 sp
s character in CH bonds 25% 33% 50%
Approximate acidity as measured by Ka (pKa) 10 62 (62) 10 45 (45) 10 26 (26)
electron in a 2p orbital, it follows that an electron in an orbital with mores character will be closer to the nucleus and
more strongly held than an electron in an orbital with lesss character. Thus, when ansp orbital of carbon overlaps with
a hydrogen 1s orbital to give a CH bond, the electrons are held more strongly and the bond is stronger and shorter
than electrons in a bond between hydrogen andsp2-hybridizedcarbon. Similar reasoning holds for the shorter CC
bond distance of acetylene compared to ethylene, although here the additional bond in acetylene is also a factor.
The pattern is repeated in higher alkynes as shown when comparing propyne and propene. The bonds to the sp-
hybridizedcarbons of propyne are shorter than the corresponding bonds to thesp2 hybridized carbons of propene.
H CH3
H C C CH3 C C 151 pm

106 pm 146 pm H H
121 pm 108 pm 134 pm
Propyne Propene

An easy way to keep track of the effect of the s character of carbon is to associate it with electronegativity. As
thes character of carbon increases, so does that carbons apparent electronegativity (the electrons in the bond involving
that orbital are closer to carbon). The hydrogens in CH bonds behave as if they are attached to an increasingly more
electronegative carbon in the series ethane ethylene acetylene.

PROBLEM 9.3 How do bond distances and bond strengths change with electronegativity in the series NH 3, H2O, and
HF?

The property that most separates acetylene from ethane and ethylene is its acidity. It, too, can be explained on
the basis of the greater electronegativity of sp-hybridizedcarbon compared withsp3 and sp2.
 What are the Properties of Alkynes
October 25, 2014

by admin

5 min read

3
While answering the question what are the properties of alkynes, this article also presents you
adequate information about alkynes. Alkyne group is a member of the hydrocarbon family;
contains a Carbon-Carbon triple bond in their structure. Alkynes possess similar physical
properties as alkanes and alkenes. Alkynes are more reactive than alkanes and alkynes show
reactions similar to alkanes. This article briefly explains about the similar properties which alkynes
share with the other hydrocarbons and the differences which they possess. Similar to alkanes and
alkenes, alkynes also have cyclic members apart from the acyclic (non-cyclic) members. However,
this article focuses only on the acyclic alkynes, which have the general molecular formula of C nH2n-
2.

What are Alkynes

Alkynes are a category of hydrocarbons containing a Carbon-Carbon triple (C=C) bond. Because
of the triple bond, an alkyne has four fewer hydrogen atoms than its corresponding alkane. Similar
to alkanes and alkenes, alkynes also form both cyclic and non-cyclic molecular structures. The
general molecular formula for acyclic (non-cyclic) alkanes is CnH2n-2 and that of cyclic alkanes is
CnH2n-4. Some properties of alkynes are different from other hydrocarbons.
General Molecular Formula of Alkynes
Acyclic alkanes have the general molecular formula of CnH2n-2. The smallest alkane is Methane
(Acetylene C2H2). Alkynes that have triple bonds at the end of Carbon chain (RC=H), are
called terminal alkynes or monosubstituted alkynes. As a group, terminal alkynes are the most
acidic hydro carbon group. Disubstituted alkynes have internal triple bonds (RC=R).
Chemical Properties of Alkynes
Molecular structure of alkynes
The Carbon-Carbon triple bond has the linear geometry. It characterizes the -C=C- and C-C=C-C
units of terminal and internal triple bonds respectively.The triply bonded Carbon atoms are sp-
hybridized.

Acidity of terminal alkynes

The =C-H bond of the alkynes shows little tendency to ionize. However, alkanes and alkenes are
all weak acids.

Reactivity of alkynes
Unlike alkanes, alkynes show many reactions with chemical reagents. Most of them are addition
reactions as in alkenes. However, terminal alkynes undergo substitution reactions too.

In general, both of alkanes and alkynes are more reactive than alkanes and alkenes. Alkynes
undergo similar types of reactions. For example, they both undergo electrophilic addition reactions
with halogens, acids and oxidizing agents. One of the most significant differences in chemical
reactivity between alkenes and alkynes is due to the differences in acidity. Terminal alkynes
contain an acidic hydrogen that can be removed by a strong base to yield an acetylide anion. As
acetylide anions negative charge is in a hybrid orbital with more of s character, which allow the
charge to be closer to the nucleus, it is more stable than either alkyl anion or vinylic anion.

Alkanes and alkenes do not react as follows.

Physical Properties of Alkynes

Alkynes resemble the alkenes and alkanes in physical properties.The molecules that have a lower
molecular weight are gases at room temperature and as the molecular weight increases their
physical state changes from gas to liquid and then to solids.

Solubility of Alkynes
Both alkenes and alkynes are relatively polar molecules. Therefore, both of these groups are
soluble in polar solvents or solvents in low polarity. Alkynes are slightly soluble in water; that of
alkanes is lower than the alkynes.

Alkynes solubility in water > Alkenes solubility in water

Density of Alkynes
Alkynes have a low-density value as alkanes and alkenes. The densities of alkynes are usually less
than that of water. (Ref: Table 2)

Boiling points of Alkynes

Generally, alkynes have slightly higher boiling points than the corresponding alkanes and alkenes.

Example:
Alkane Alkene Alkyne
Butane Butene 1-Butyne 2-
butyne
00C 60C 8.10C 27.0 0C

Properties of Alkynes Summary

Alkynes are a group in hydrocarbon family that have a Carbon-Carbon triple bond in the structure.
Acyclic alkynes have the general chemical formula of C nH2n-2, and that of cyclic alkyne is CnH2n-4.
Acetylene is the smallest member in alkyne group. Terminal alkynes are the most acidic group in
hydrocarbon family. Alkynes undergo both addition and substitution reactions. Alkynes are more
reactive than alkanes.
Alkynes resemble alkanes and alkynes in physical properties (boiling point, solubility in water,
dipole moment). Solubility of alkynes in water is slightly higher than the other hydrocarbons.Their
densities are lower than that of water as other hydrocarbons.