Unit IV- Hydrocarbons

Hydrocarbons are carbon-containing organic compounds that

provide a source of energy and raw materials. They are the simplest
organic compounds which contain only elements carbon and hydrogen.

Learning Outcomes

At the end of this unit, you will be able to:

 Differentiate saturated and unsaturated hydrocarbons.
 Name, draw, and construct molecular models of alkanes, alkenes and alkynes
 Describe where hydrocarbons are obtained and how they are separated

Pretest

Direction: Answer the following questions:

1. Name two uses of methane or natural gas in your home or community.

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2. Explain why carbon forms many compounds.

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Gracias! The key answer is found on page ____ or you may

check it out in our google classroom with the code _____.
 Content

Models of Hydrocarbons

The ball-and –stick model demonstrates the geometry of the

molecule clearly, but the space-filling model gives a more realistic picture
of what a molecule would look if you could see it.

Carbon atoms can bond to each other not only by single covalent
bonds but also by double bond and triple covalent bonds.

In the nineteenth century, chemists experimented with

hydrocarbons obtained from heating animal fats and plat oils. They
classified these hydrocarbons according to chemical test in which they
mixed each hydrocarbons with bromine and then measure how much
reacted with the hydrocarbon. Some hydrocarbons would react with a
small amount of bromine, some would react with more , and some would
not react with any amount of bromine. Chemists called the hydrocarbons
that reacted with bromine unsaturated while hydrocarbons that did not
react with bromine were said to be saturated.

Hydrocarbons that reacted with bromine had double or triple

covalent bonds while those that did not react had only single covalent
Figure 3.1 Carbon can bond to
bonds. other carbon atoms in double and
triple bonds. These Lewis
structures and structural formulas
Saturated Hydrocarbon- a hydrocarbon having only a single bonds. show two ways to denote double
and triple bonds.

- The carbon atoms in saturated hydrocarbons form bonds to the maximum amount of
hydrogen atoms possible.
- These compounds are saturated with hydrogen atoms.
- Include alkanes (straight chains) & cycloalkanes (carbon rings)
Unsaturated Hydrocarbon- a hydrocarbon that has at least one double or triple bond between
carbon atoms.
 - The carbon atoms in unsaturated hydrocarbons form bonds to less than the maximum
amount of hydrogen atoms possible
- These compounds are not saturated with hydrogen atoms (unsaturated) due to the
presence of double or triple carbon to carbon bonds

Figure 3.1. The difference between saturated and unsaturated hydrocarbons

Source: BIOB111_SN08_Lecture_PropertiesFunctGroups.pdf

Refining Hydrocarbons

Petroleum is a fossil fuel where hydrocarbons are obtained. It is formed from the remains
of microorganisms that lived in Earth’s ocean million years ago.

It is more useful to humans when it is separated into simpler components or fractions

Separation is carried out in a process called fractional distillation, also called fractionation which
involves boiling the petroleum and collecting components or fractions as they condense at
different temperature.

Click the links below to watch a video on how fractional distillation is done in
a fractioning tower.
https://www.youtube.com/watch?v=PYMWUz7TC3A
https://www.youtube.com/watch?v=CjmriZq5xRo

Alkanes
 - Hydrocarbons containing single bond.
- These are non-polar compounds.
- It has a general formula of CnH2n + 2
- The simplest alkane (that is, with n 5 1) is methane CH4, which is a natural product
of the anaerobic bacterial decomposition of vegetable matter under water.
Straight Chain Alkanes

- These are alkanes of which the carbon atoms are connected in one
continuous chain with no branches.

Table 3.1. Straight Chain Alkanes

Source: Chang, Chemistry © 2010, 10e, Student Edition (Reinforced Binding) 10th edition by Chang, Raymond (2009)
Hardcover (10th ed.). (2021). Glencoe/McGraw-Hill.

IUPAC Rules for Alkane Nomenclature

1. Find and name the longest continuous carbon chain.

2. Identify and name groups attached to this chain.
3. Number the chain consecutively, starting at the end nearest a substituent group.
4. Designate the location of each substituent group by an appropriate number and name.
5. Assemble the name, listing groups in alphabetical order using the full name (e.g.
cyclopropyl before isobutyl). The prefixes di, tri, tetra etc., used to designate several groups of
the same kind, are not considered when alphabetizing.

Branched- Chain Alkanes

- When naming branched-chain alkanes, the longest continuous chain of carbon atom
is called the parent chain. All side branches are called substituent groups because
they appear to substitute for a hydrogen atom in the straight chain.
- The substituent groups are called alkyl groups.
Alkyl groups - Once an alkane loses one of its hydrogen atoms it becomes an alkyl
group
Naming: replace the -ane with -yl at the end of the name – Methane becomes methy

Table 3.2. Common Alkyl Groups

Source: file:///D:/FILES/Documents/2020-2021/2ND%20SEMESTER/SPEC%20102-S/hYDROCARBONS.pdf

Naming Branched-chain Alkanes

1. Count the number of carbon atoms in the longest continuous chain.

2. Number each carbon in the parent chain. Locate the end carbon closest to a
substituent group. Label the carbon Position 1 . This step gives all the
substituent groups the lowest position numbers possible.
3. Name each alkyl group substituent. Place the name of the group before the
name of the parent chain.
4. If the same alkyl group occurs more than once as a branch on the parent
structure, use a prefix (di-, tri-, tetra-, and so on) before its name to indicate
how many times it appears. Then, use the number of the carbon to which each
is attached to indicate its position.
5. When different alkyl groups are attached to the same parent structure, place
their names in alphabetical order. Do not consider the prefixes (di-, tri-, and so
on) when determining alphabetical order.
6. Write the entire name, using hyphens to separate numbers from words and
commas to separate numbers. Do not add a space between the substituent
name and the name of the parent chain.
 Cycloalkanes

o Alkanes whose carbon atoms are joined in rings.

o They have the general formula CnH2n, where n 5 3, 4, . . . .
o The simplest cycloalkane is cyclopropane, C3H6

Figure 3.1 Structures of the first four cycloalkanes and their simplified forms.

Reactions of Alkanes

A. Combustion
 Combustion reactions are exothermic reactions that release heat
 Alkanes burn in the presence of oxygen producing CO2 , H2O and heat
via combustion reactions.
 All combustion reactions are redox reactions where one reactant is
oxidised and one is reduced. Oxygen is always reduced in redox
reactions

B. Halogenation
 Halogenation reactions involve an alkane reacting with a halogen
molecule such as Cl2 or F2
 the replacement of one or more hydrogen atoms by halogen atoms

 The lost hydrogen atom forms a compound with the other halogen atom
(from the halogen molecule), in this case creating the strong acid HCl

 Alkanes in which one or more hydrogen atoms have been replaced by

a halogen atom are called alkyl halides. Among the large number of
alkyl halides, the best known are chloroform (CHCl3), carbon
tetrachloride (CCl4), methylene chloride (CH2Cl2), and the
chlorofluorohydrocarbons.
  Chloroform is a volatile, sweet-tasting liquid that was used for many
years as an anesthetic. However, because of its toxicity (it can severely
damage the liver, kidneys, and heart) it has been replaced by other
compounds.
 Carbon tetrachloride, also a toxic substance, serves as a cleaning
liquid, for it removes grease stains from clothing.
 Methylene chloride is used as a solvent to decaffeinate coffee and as
a paint remover.
Alkenes and Alkynes

- Alkenes are hydrocarbons that contain at least double bond, and alkynes are
hydrocarbons that contain at least one triple bond.
- They are unsaturated hydrocarbons
- Alkenes have the general formula CnH2n, where n 5 2, 3, . . . .
Alkene Nomenclature

1. Indicate the positions of the carbon-carbon double bonds.

2. The names of compounds containing CPC bonds end with –ene
3. As with the alkanes, the name of the parent compound is determined by the number
of carbon atoms in the longest chain.

4. The numbers in the names of alkenes refer to the lowest numbered carbon atom in
the chain that is part of the CPC bond of the alkene.
5. Alkene nomenclature must specify whether a given molecule is cis or trans if it is a
geometric isomer, such as

In the cis isomer, the two H atoms are on the same side of the CPC bond; in the trans
isomer, the two H atoms are across from each other.

Properties and Reactions of Alkenes

- Ethylene is an extremely important substance because it is used in large quantities for

the manufacture of organic polymers and in the preparation of many other organic
chemicals. Ethylene is prepared industrially by the cracking process, that is, the
thermal decomposition of a large hydrocarbon into smaller molecules. When ethane
is heated to about 800°C, it undergoes the following reaction:
- Alkanes contain only single carbon to carbon bonds, which require
significant input energy to break
• Difficult to replace hydrogen atoms attached to carbons with other atoms (e.g.
halogens Cl, F)
– Alkanes stable and unreactive
- Once a double or triple carbon to carbon bond has been broken:
• Other atoms can bond to the carbon atoms that were previously part of the multiple
carbon to carbon bond
– Carbon must have 4 covalent bonds at all times to be stable

- Breaking a multiple carbon to carbon bond creates new positions where carbon atoms can
form covalent bonds to other atoms.

Hydrogenation Reaction

- Addition of a H2 molecule into an alkene:

o Replaces the double carbon to carbon bond with two new covalent bonds
between the carbon atoms and the added hydrogen atoms

- End result: the alkene is converted to an alkane

o The carbon atoms that form the new bonds with the added hydrogen atoms
were previously part of the double carbon to carbon bond

Hydration Reaction
 - Addition of a H2O molecule into an alkene:
o Replaces the double carbon to carbon bond with two new covalent bonds
between one carbon atom and H, a second carbon atoms and an OH group.

- End result: the alkene is converted to an alcohol (contains the alcohol functional group)
o The carbon atoms that form the new bonds with the H and OH were previously
part of the double carbon to carbon bond

Halogenation reaction

- Addition of a halogen molecule (e.g. Cl2 ) into an alkene:

 Replaces the double carbon to carbon bond with two new covalent bonds
between the carbon atoms and the added halogen atoms
- End result: the alkene is converted to a halogenated alkane
o The carbon atoms that form the new bonds with the added halogen atoms were
previously part of the double carbon to carbon bond .
o Each halogenation reaction with an alkene adds two halogen atoms at a time

- Bromine is a halogen (Br2) that can readily be added into an alkene via a halogenation
reaction
Alkynes

- Alkynes contain at least one carbon-carbon triple bond. They have the general formula
CnH2n 2 2, where n 5 2, 3, . .
Alkyne Nomenclature

1. Names of compounds containing C ‚ C bonds end with -yne.

 2. Again, the name of the parent compound is determined by the number of carbon atoms
in the longest chain
3. As in the case of alkenes, the names of alkynes indicate the position of the carbon-
carbon triple bond, as, for example, in

Properties and Reactions of Alkynes

- The simplest alkyne is ethyne, better known as acetylene (C2H2)

- Acetylene is a colorless gas (b.p. 284°C) prepared by the reaction between calcium
carbide and water:

- Alkynes can participate in many of the same chemical reactions as alkenes:

o Hydrogenation Reaction- addition of a H2 molecule
o Hydration Reaction – addition of a H2O molecule which creates alcohol
o Halogenation reaction- addition of a halogen molecule

Aromatic compounds

- Aromatic compounds are special types of compounds.

- These include benzene and other related ring compounds (benzenoid). Like alicyclic
compounds, aromatic compounds may also have hetero atom in the ring. Such
compounds are called hetrocyclic aromatic compounds. Some of the examples of
various types of aromatic compounds are:
 Benzenoid aromatic compounds. They are characterized by the presence of one
or more fused or isolated benzene rings as well as their derivatives in their structure.
Depending upon the number of benzene rings that are fused together in their
structure, they can be further classified as Monocyclic, Bicyclic, Tricyclic.

 Non-Benzenoid aromatic Compounds: They are characterized by the presence

of a single benzene ring to which other groups are attached.
 - When benzene was discovered scientists were puzzled
o Benezene had multiple double carbon to carbon bonds but was stable
o Benzene behaved more like an alkane than an alkene or alkyne
o Benzene continually switches between two forms where the positions of
the double and single carbon to carbon bonds alternate
- The two forms of benzene are called resonance structures

- In the benzene ring:

o Every carbon atom is attached to two other carbon atoms by at least one
carbon to carbon bond
o 3 extra carbon to carbon bonds in the benzene ring are formed by 6
electrons (2 electrons for each bond)
o The extra bonds alternate their positions (see the resonance structures
below)

Nomenclature of Aromatic Compounds

1. The naming of monosubstituted benzenes, that is, benzenes in which one H atom has
been replaced by another atom or a group of atoms, is quite straightforward, as shown
here:
 2. If more than one substituent is present, we must indicate the location of the second
group relative to the fi rst. The systematic way to accomplish this is to number the
carbon atoms as follows:

Three different dibromobenzenes are possible:

3. The prefi xes o- (ortho-), m- (meta-), and p- (para-) are also used to denote the relative
positions of the two substituted groups, as shown above for the dibromobenzenes.
4. Compounds in which the two substituted groups are different are named accordingly.
Thus,is named 3-bromonitrobenzene, or m-bromonitrobenzene.

5. Finally, we note that the group containing benzene minus a hydrogen atom (C6H5) is
called the phenyl group. Thus, the following molecule is called 2-phenylpropane:

Properties and Reactions of Aromatic Compounds

 - Aromatic compounds are less reactive than alkenes, making them useful industrial
solvents for nonpolar compounds.
- Aromatic compounds, originally named because of their fragrant properties, are
unsaturated hydrocarbon ring structures that exhibit special properties, including
unusual stability, due to their aromaticity.
- Aromatic compounds are generally nonpolar and immiscible with water. As they are
often unreactive, they are useful as solvents for other nonpolar compounds. Due to
their high ratio of carbon to hydrogen, aromatic compounds are characterized by a
sooty yellow flame.
Electrophilic Aromatic Substitution- The electron-rich benzene makes a bond with an electron-
deficient chemical species (E+, the electrophile) which takes the place of an H-atom in the original
structure. The reaction preserves the pi system of electrons and therefore the aromatic character
of the benzene ring.

For further details and understanding, you may watch the following videos;
a. Hydrocarbons and
alkaneshttps://www.youtube.com/watch?v=ykIFTtTjoso
b. Alkanes https://www.youtube.com/watch?v=F8J2FirbIxg
c. Cracking Crude Oil and Alkenes
https://www.youtube.com/watch?v=bOiYLKX9ZRY
d. Addition Reaction of Alkenes
https://www.youtube.com/watch?v=83Is-rouV-U

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