Hydrocarbon

Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc

Hydrocarbon: In organic chemistry, a hydrocarbon is an organic compound
consisting entirely of hydrogen and carbon. Hydrocarbons from which one
hydrogen atom has been removed are functional groups, called hydrocarbyls.

Alkanes: CnH(2n+2)
Alkanes are organic compounds that consist entirely of single-bonded carbon and
hydrogen atoms and lack any other functional groups. Alkanes have the general
formula, CnH(2n+2) and can be subdivided into the following three groups: the linear
straight-chain alkanes, branched alkanes, and cycloalkanes.

1. Structure of Alkanes {CnH(2n+2)}

where n = number of carbon atoms in the alkane molecule

The alkanes comprise a series of compounds that are composed of carbon and
hydrogen atoms with single covalent bonds. This group of compounds comprises a
homologous series with a general molecular formula of C n H 2 n+2 , where equals any
integer.
The simplest alkane, methane, has one carbon atom and a molecular formula of CH 4 .
Because this compound contains only single covalent bonds, its structural formula is

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc

2. Nomenclature:
The IUPAC nomenclature (systematic way of naming compounds) for alkanes is
based on identifying hydrocarbon chains. Unbranched, saturated hydrocarbon chains
are named systematically with a Greek numerical prefix denoting the number of
carbons and the suffix "-ane".
It is difficult or impossible to find compounds with more than one IUPAC name.
This is because shorter chains attached to longer chains are prefixes and the
convention includes brackets. Numbers in the name, referring to which carbon a
group is attached to, should be as low as possible, so that 1- is implied and usually
omitted from names of organic compounds with only one side-group. Symmetric
compounds will have two ways of arriving at the same name.

Alkanes are hydrocarbon that have only sp 3 carbons and hydrogens. Each
carbon atom in the molecule is surrounded by single covalent bonds. Each carbon in
an alkane is connected to four atoms in a tetrahedral geometry. Due to this geometry
and the small diffence in electronegativity between hydrogen and carbon, alkanes are
non-polar molecules. The general molecular formula for alkanes is:

CnH2n+2

where n = number of carbon atoms in the alkane molecule

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
Root +ane (Here Root are like Meth, Eth, Prop, But, Pent, Hex, Hept,
Oct, Non and Dec respectively for the numbers of carbon are 1, 2, 3, 4, 5, 6, 7,
8, 9, and 10)
3. Isomerism of Alkanes:
Alkanes with more than three carbon atoms can be arranged in various different ways,
forming structural isomers. The simplest isomer of an alkane is the one in which the
carbon atoms are arranged in a single chain with no branches. This isomer is
sometimes called the n-isomer (n for "normal", although it is not necessarily the most
common). However the chain of carbon atoms may also be branched at one or more
points. The number of possible isomers increases rapidly with the number of carbon
atoms. For example:

• C1: methane only

• C2: ethane only
• C3: propane only
• C4: 2 isomers: n-butane and isobutane
• C5: 3 isomers: pentane, isopentane, and neopentane
• C6: 5 isomers: hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane,
and 2,3-dimethylbutane
• C12: 355 isomers
• C32: 27,711,253,769 isomers
• C60: 22,158,734,535,770,411,074,184 isomers, many of which are not stable.
Branched alkanes can be chiral. For example 3-methylhexane and its
higher homologues are chiral due to their stereogenic center at carbon atom number
3. In addition to the alkane isomers, the chain of carbon atoms may form one or more
loops. Such compounds are called cycloalkanes.

Comparison of nomenclatures for three isomers of C5H12

Common name n-pentane isopentane neopentane

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
IUPAC name pentane 2-methylbutane 2,2-dimethylpropane

Structure

In chemistry, isomers (/ˈaɪsəmərz/; from Greek ἰσομερής, isomerès; isos = "equal",

méros = "part") are molecules with the same chemical formula but different chemical
structures. That is, isomers contain the same number of atoms of each element, but
have different arrangements of their atoms in space.

4. General Methods of Preparation:

When sodium salt of carboxulic acid is heated with soda lime (NaOH +CaO), then
Alkane is produced. Here CO2 is eliminated from carboxyl group part of sodium salt
as sodium carbonate. That is why this reaction is known as Decarboxylation.
For example:
R-COONa+ NaO--H(CaO) ----heat -->R-H + Na2CO3 (CaO)
Sodium alkanoate Soda Lime Alkane

Preparation of Methane and Ethane:

A mixture of dry sodium ethanoate and soda lime is heated; then Methane and
sodium carbonate are produced.
CH3COONa + NaOH (CaO) ----heat --> CH4 + Na2CO3 (CaO)
Sodium ethanoate Soda Lime Methane

But for ethane, a mixture of dry sodium propanoate and soda lime is heated;
then ethane gas and Na 2CO3 are produced.
CH3—CH2--COONa + NaOH (CaO)----heat--> CH3—CH3 + Na2CO3 (CaO)
Sodium propanoate Soda Lime Ethane

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc

5. Important Reaction of Alkanes:

Alkanes are generally unreactive, but can participate in oxidation, halogenation, and
cracking reactions. Source: Boundless. “Reactions of Alkanes.” Boundless Chemistry.Boundless, 25 Nov. 2014.

Identify the general reactions of alkanes

• Alkanes are stable compounds and are generally unreactive.
• The most important application of alkanes is in oxidation reactions; they are
used in internal combustion engines as fuel.
• Applying heat and a catalyst can crack larger, more complex alkanes and
produce smaller, more useful alkanes and alkenes.

Cracking
The thermal decomposition of a substance, especially that of crude petroleum, in
order to produce petrol/gasoline.
Radical
A group of atoms joined by covalent bonds that are characterized by a free, unpaired
electron that imparts their reactivity.
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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
1. Structure of Alkenes {CnH2n}
where n = number of carbon atoms in the alkene molecule

Alkenes are hydrocarbons with carbon-to-carbon double bonds (R2C=CR2) and alkynes are

hydrocarbons with carbon-to-carbon triple bonds (R–C≡C–R). Collectively, they are

called unsaturated hydrocarbons because they have fewer hydrogen atoms than does an alkane w it h

the same number of carbon atoms, as is indicated in the following general formulas:

Some representative alkenes—their names, structures, and physical properties—are given bellow

Table 1.1 Physical Properties of Some Selected Alkenes

IUPAC Molecular Condensed Structural Melting Boiling

Name Formula Formula Point (°C) Point (°C)

ethene C2H4 CH2=CH2 –169 –104

propene C3H6 CH2=CHCH3 –185 –47

1-butene C4H8 CH2=CHCH2CH3 –185 –6

1-pentene C5H10 CH2=CH(CH2)2CH3 –138 30

1-hexene C6H12 CH2=CH(CH2)3CH3 –140 63

1-heptene C7H14 CH2=CH(CH2)4CH3 –119 94

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
IUPAC Molecular Condensed Structural Melting Boiling
Name Formula Formula Point (°C) Point (°C)

1-octene C8H16 CH2=CH(CH2)5CH3 –102 121

We used only condensed structural formulas in Table 1.1 "Physical Properties of Some Selected

Alkenes". Thus, CH 2=CH 2 stands for

The double bond is shared by the two carbon atoms and does not involve the hydrogen atoms,
although the condensed formula does not make this point obvious. Note that the molecular form u la
for ethene is C2H 4, whereas that for ethane is C2H 6.

The first two alkenes in Table 1.1 "Physical Properties of Some Selected Alkenes"—
ethene and propene (Figure 1.1 "Ethene and Propene")—are most often called by
their common names—ethylene and propylene, respectively. Ethylene is a major
commercial chemical. The US chemical industry produces about 25 billion kilograms
of ethylene annually, more than any other synthetic organic chemical. More than half
of this ethylene goes into the manufacture of polyethylene, one of the most familiar
plastics.

Figure 1.1 Ethene and Propene

The ball-and-spring models of ethene/ethylene (a) and propene/propylene (b) show their

respective shapes, especially bond angles.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
Note
Although there is only one alkene with the formula C2H4 (ethene) and only one with
the formula C3H6 (propene), there are several alkenes with the formula C4H8.

The simplest alkene, ethene, has two carbon atoms and a molecular formula of C 2H 4.
The structural formula for ethene is

In longer alkene chains, the additional carbon atoms are attached to each other by
single covalent bonds. Each carbon atom is also attached to sufficient hydrogen
atoms to produce a total of four single covalent bonds about itself. In chains with
four or more carbon atoms, the double bond can be located in different positions,
leading to the formation of structural isomers. For example, the alkene of molecular
formula C4H 8 has two isomers.

Stereoisomers. In addition to structural isomers, alkenes also

formstereoisomers. Because rotation around a multiple bond is restricted, groups
attached to the double‐bonded carbon atoms always remain in the same relative
positions. These “locked” positions allow chemists to identify various isomers from
the substituents' locations. For example, one structural isomer of C 5H 10 has the
following stereoisomers.

The isomer on the left, in which the two substituents (the methyl and ethyl groups)
are on the same side of the double bond, is called the cis isomer, while the isomer on
the right, with two nonhydrogen substituents on opposite sides of the double bond, is
called the trans isomer.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
If more than two substituents are attached to the carbon atoms of a double bond,
the cis and trans system cannot be used. With such chemicals, E‐Z notation is used. In
the E‐Z system, the molecule is first bisected vertically through the double bond.
Second, the two atoms or groups on each carbon atom are ranked by atomic weight.
The higher atomic weight is assigned priority. For example, in Figure , the carbon and
chlorine atoms on the left side of the bisecting line are ranked. Chlorine has priority
because it is heavier. On the right side, bromine outranks carbon. Third, the positions
of the two atoms of higher rank are determined. If the two atoms are in
the cis position, the arrangement is Z (for German zusammen, meaning “together”). If
the atoms or groups are in the trans position, the arrangement is E(for
German entgegen, meaning “opposite”).

The name of the chemical in Figure is ( E)‐2‐bromo‐3‐chloro‐2‐butene.

2. Nomenclature:
Here are some basic rules for naming alkenes from the International Union of Pure
and Applied Chemistry (IUPAC):

1. The longest chain of carbon atoms containing the double bond is considered the
parent chain. It is named using the same stem as the alkane having the same
number of carbon atoms but ends in -ene to identify it as an alkene. Thus the
compound CH2=CHCH3 is propene.
2. If there are four or more carbon atoms in a chain, we must indicate the
position of the double bond. The carbons atoms are numbered so that the first
of the two that are doubly bonded is given the lower of the two possible
numbers. The compound CH 3CH=CHCH2CH3, for example, has the double

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
bond between the second and third carbon atoms. Its name is 2-pentene (not
3-pentene).
3. Substituent groups are named as with alkanes, and their position is indicated by
a number. Thus,

is 5-methyl-2-hexene. Note that the numbering of the parent chain is always

done in such a way as to give the double bond the lowest number, even if that
causes a substituent to have a higher number. The double bond always has priority in
numbering.

3. Isomerism of Alkenes:

Structural isomerism
All the alkenes with 4 or more carbon atoms in them show structural isomerism.
This means that there are two or more different structural formulae that you can draw
for each molecular formula.

For example, with C4H8, it isn't too difficult to come up with these three structural
isomers:

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc

H H H
| | |

but-1-ene C = C - C - C -H
C4H8
(1-butene)
| | | |
H H H H

H H
| |
but-2-ene
H- C - C = C - C -H C4H8
(2-butene)
| | | |
H H H H

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
H H
| |

C =C - C -H
2-methylprop-1-ene
| | | C4H8
(2-methylpropene)
H H-C-H H

|
H

H H
| |

H- C - C -H

cyclobutane | | C4H8

H- C - C -H

| |
H H

But-1-ene, but-2-ene, 2-methylprop-1-ene and cyclobutane are structural isomers.

They have the same molecular formula, C 4H8, but different structural formulae.

4. General Methods of Preparation:

Heating most alcohols is a general method of preoaration of alkenes. Heating
alcohols with a strong acid causes them to lose a molecule of water (to dehydrate)
and form an alkene.

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 Hydrocarbon
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The reaction is an elimination and is favoured at higher temperatures. The most

commonly used acids in the laboratory are Bronsted acids - proton donors such as
sulphuric acid and phosphoric acid. Lewis acids such as alumina (Al2O3) are often
used in industrial, gas phase dehydrations.
Dehydration reactions of alcohols show several important characteristics which
shall be explained.
The experimental conditions-temperature and acid concentration-that are required
to bring about dehydration are closely related to the structure of the individual
alcohol. Alcohols in which the hydroxyl group is attached to a primary carbon
(primary alcohols) are the most difficult to dehydrate. Dehydration of ethanol, for
example, requires concentrated sulphuric acid and a temperature of 180°C.
CH3—CH2-OH + H-OSO3H ---1000C-- CH3—CH2—OSO3H + H2O
Ethanol Sulfuric Acid Ethyl Hydrogen Sulphate Water

CH3—CH2—OSO3H ----------1650C--------- CH2=CH2+ H2O

Ethyl Hydrogen Sulphate Ethene Water

Secondary alcohols usually dehydrate under milder conditions. Cyclohexanol, for

example, dehydrates in 85% phosphoric acid at 165-170°C.

Tertiary alcohols are usually so easily dehydrated that extremely mild conditions
can be used, ter-butyl alcohol, for example, dehydrates in 25% H2SO4 at a
temperature of 85°C.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc

Thus, overall, the relative ease with which alcohols undergo dehydration is in the
following order
Ease of Dehydration: 3° Alcohol > 2° Alcohol > 1° Alcohol
This behaviour, is related to the stability of the carbocation formed in each
reaction.
Some primary and secondary alcohols also undergo rearrangements of their carbon
skeleton during dehydration.

5. Important Reaction of Alkenes:

Although the double bond between two carbon atoms is stronger link than a single
bond, it is not twice as strong, (i.e. the second bond formed between the carbon
atoms is weaker than the first). Thus, the second bond is more vulnerable to attack by
suitable reagents, even under fairly mild conditions. Thus, the reaction of this second
bond tend to be addition reactions, where the unsaturated carbon atoms become
saturated. The alkenes are much more reactive than alkanes.
Addition of Hydrogen
The alkenes are readily reduced by the addition of hydrogen across the double
bond to form alkanes (i.e. reduction of alkenes).
For example, when an alkenes is passed over a nickel (Ni) catalyst at 1500C, the
alkene is reduced to an alkane.

H2C=CH2 + H2 =1500C=> CH3CH3

Ethene Ethane

Addition of Halogen
• Halogens readily add across the double bond of the alkenes to form dihalides

H2C=CH2 + Cl2 ==> CH2Cl--CH2Cl

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
Ethene DiChloroEthane

• Unsaturated ethene reacts with red Br 2 solution to form colourless 1, 2-

dibromo ethane. Then the solution becomes colourless for want of bromine
molecule.
H2C=CH2+Br2======CCl4=====>H2Br--CH2Br
Ethene 1, 2-DiBromoEthane

Alkynes: CnH(2n-2)
Alkynes are organic molecules made of the functional group carbon-carbon triple
(H–C≡C--H) bonds. They are written in the empirical formula of CnH2n-2. They are
unsaturated.

1. Structure of Alkynes {CnH2n-2}

where n = number of carbon atoms in the alkyne molecule

The alkynes comprise a series of carbon‐ and hydrogen‐based compounds that

contain at least one triple bond. This group of compounds is a homologous series
with the general molecular formula of CnH2n-2, where n equals any integer greater
than one.

The simplest alkyne, ethyne (also known as acetylene), has two carbon atoms and the
molecular formula of C2H 2. The structural formula for ethyne is
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 Hydrocarbon
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2. Nomenclature:
Alkynes are organic molecules made of the functional group carbon-carbon triple
bonds and are written in the empirical formula of [Math Processing Error]. 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.

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.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
Example 2

(2-bromo-1,1-dimethylcyclohexane)

Notice that "f" of fluoro alphabetically precedes the "m" of methyl. Although "di"
alphabetically precedes "f", it is not used in determining the alphabetical order.

Example 3

(2-fluoro-1,1,-dimethylcyclohexane NOT 1,1-dimethyl-2-fluorocyclohexane)

8) If the substituents of the cycloalkane are related by the cis or trans configuration,
then indicate the configuration by placing "cis-" or "trans-" in front of the name of
the structure.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc

Blue=Carbon Yellow=Hydrogen Green=Chlorine

Notice that chlorine and the methyl group are both pointed in the same direction on
the axis of the molecule; therefore, they are cis.

cis-1-chloro-2-methylcyclopentane
9) After all the functional groups and substituents have been mentioned with their
corresponding numbers, the name of the cycloalkane can follow.

Reactivity
Cycloalkanes are very similar to the alkanes in reactivity, except for the very small
ones, especially cyclopropane. Cyclopropane is significantly more reactive than what is
expected because of the bond angles in the ring. Normally, when carbon forms four
single bonds, the bond angles are approximately 109.5°. In cyclopropane, the bond
angles are 60°.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
With the electron pairs this close together, there is a significant amount of repulsion
between the bonding pairs joining the carbon atoms, making the bonds easier to
break.

Alcohol Substituents on Cycloalkanes

Alcohol (-OH) substituents take the highest priority for carbon atom numbering in
IUPAC nomenclature. The carbon atom with the alcohol substituent must be labeled
as 1. Molecules containing an alcohol group have an ending "-ol", indicating the
presence of an alcohol group. If there are two alcohol groups, the molecule will have a
"di-" prefix before "-ol" (diol). If there are three alcohol groups, the molecule will
have a "tri-" prefix before "-ol" (triol), etc.

Example 4

The alcohol substituent is given the lowest number even though the two methyl
groups are on the same carbon atom and labeling 1 on that carbon atom would give
the lowest possible numbers. Numbering the location of the alcohol substituent is
unnecessary because the ending "-ol" indicates the presence of one alcohol group on
carbon atom number 1.

2,2-dimethylcyclohexanol NOT 1,1-dimethyl-cyclohexane-2-ol

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 Hydrocarbon
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Blue=Carbon Yellow=Hydrogen Red=Oxygen

Example 5

3-bromo-2-methylcyclopentanol NOT 1-bromo-2-methyl-cyclopentane-2-ol

trans-cyclohexane-1,2-diol

Other Substituents on Cycloalkanes

There are many other functional groups like alcohol, which are later covered in an
organic chemistry course, and they determine the ending name of a molecule. The

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
naming of these functional groups will be explained in depth later as their chemical
properties are explained.

Name Name ending

alkene -ene

alkyne -yne

alcohol -ol

ether -ether

nitrile -nitrile

amine -amine

aldehyde -al

ketone -one

carboxylic acid -oic acid

ester -oate

amide -amide

Although alkynes determine the name ending of a molecule, alkyne as a substituent on

a cycloalkane is not possible because alkynes are planar and would require that the
carbon that is part of the ring form 5 bonds, giving the carbon atom a negative
charge.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
However, a cycloalkane with a triple bond-containing substituent is possible if the
triple bond is not directly attached to the ring.

Example

Ethynylcyclooctane

Example

1-propylcyclohexane

1. Isomerism of Alkynes:
Why do geometric isomers exist in alkenes, but not in alkynes?
There is restricted rotation with alkynes too, but rotation around the triple bond
wouldn't form a different compound as it could with a double bond. Think about the
shape of the molecules; alkynes are linear with two substituents, one on each end.
Alkenes are not linear: there are four distinct positions where different groups can be.

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
Switching the position of two of the groups at one end of an alkene can form a
geometric isomer, but in an alkyne there aren't two distinct groups to switch!
alkynes have a triple bond which ristricts these of having 4 extra bonds (2 per C
making the triple bond)which you should have when considering a geometric
isotomer

Alkynes are unsaturated hydrocarbons that have one or more carbon-carbon triple
bonds. Alkynes with four carbons or more exist as more than one constitutional
isomer. A constitutional isomer is a compound with the same molecular formula but a
different atom-to-atom bonding sequence.

The different atom-to-atom bonding sequence may be due

to a difference in the carbon skeleton (as seen for alkanes) or to a difference in
the position of the triple bond.

C–C–C–C
C≡ C–C–C
C– C≡C–C

Consider a linear C4 carbon skeleton. This has two different bonding environments
for carbon (red and blue).

A triple bond can be between a red carbon and a blue carbon OR between two blue
carbons.
There are therefore two possible alkyne constitutional isomers for this carbon
skeleton.

The number of alkyne constititonal isomers for a particular carbon skeleton depends
onthe number of different bonding environments for carbon AND
the number of adjacent pairs of carbon atoms where both are involved in one or fewer
bonds to other carbon atoms.

This means that neither of the triply-bonded carbons can one that bears a branch!!

When assessing the number of different bonding environments, it is important to

realise that any linear chain is symmetrical about its centre,thus bonding

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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
enviroments for carbon are the same to the left and the right of the centre.
Thus there is only one isomer above with a double bond between red and blue
carbons.
C
|
C— C— C —C — C
the presence of a branch affects the number of different bonding environments
branches of the same composition that are bonded to
the samecarbon are equivalent.The two ends of the chain may no longer be
equivalent.See the number of bonding environments for carbon in the carbon
skeleton shown at the right

2. General Methods of Preparation:

Ethyne or acetylene is prepared in the laboratory at room temperature by
adding water on calcium carbide (CaC2). Then calcium carbide is hydrolysed
to ethyne or acetylene gas and calcium hydroxide.

CaC2+ 2H2O ---------------->H — C ≡ 𝐂— 𝐇+ Ca (OH)2

OR,
CH2Br—CH2Br ---alc KOH---> CH2=CHBr--------->H — C ≡ 𝑪— 𝑯 +HBr
1, 2 – dribromo ethane vinyl bromide aeytylene

3. Important Reaction of Alkynes:

1. At above 150oC—180oC in presence of Ni-catalyst ethyne reacts with
H2 to form ethane first and then ethane.

H — C ≡ 𝐶— 𝐻 +H2---Ni150 C---> H2C—CH2---+H2Ni, 150 C---> H3C—CH3

2. At room temperature ethyne adds with bromine to form

ethynedibromide first and then ethynetetrabromide.
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 Hydrocarbon
Dr Md Mostafizul Islam Ranzu MPhil, PhD, Postdoc
H — C ≡ 𝐶— 𝐻 +Br2 ---CCl4---> HBrC—CBrH
Ethyne ethynedibromide

HBrC—CBrH +Br2 ---CCl4---> HBr2C—CBr2H

ethynedibromide ethynetetrabromide

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