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Laboratory Activity NO. 2: Structure of Hydrocarbons

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Name Group 3

Ilagan, Lineses, Maderazo, Mercado


Post-Lab
Section Schedule - Monday
2 Structure of Hydrocarbons Q1A2 – G3
Instructor Date
Sir Edu Gonzales 03/11/19

LABORATORY ACTIVITY
NO. 2
Structure
of
Hydrocarbons
Pre-Lab Questions
1. Draw the four carbon patterns commonly seen in hydrocarbons.

Butane (paraffin) Cyclpentane Propylene (olefin) Benzene (aromatic)


(naphthene)

2. Construct the Lewis Structures of the following:


a. Hexane,
CH3CH2CH2CH2CH2CH3

b. 3-hexene,
CH3CH2CHCHCH2CH3

c. 2-hexane,
CH3CCCH2CH2CH3

3. There are three distinct bond angles form in the four bonding numbers of carbon. Identify them
and in which bonding patterns is each seen?
The three distinct bond angles formed in the four bonding of carbons are 109°,
120° and 180°. The 109° is a tetrahedral that has 4 single bonds, in 120° is a trigonal
planar that has 2 single bonds and one double bond. Lastly in 180° is a linear that 2
double bonds or 1 single bonds and 1 triple bond.
4. What are olefins?
It is also called alkenes that are unsaturated carbons that contain either double or
triple bonds. Since the compound is unsaturated with respect to hydrogen atoms, the extra
electrons ae shared between 2 carbon atoms that forming double bonds in alkenes. The
reason why they called olefins because they form oily liquids on reaction in chlorine gas.

I. Introduction
The element carbon is the constituent of every organic compound. Organic
chemistry is the chemistry of carbon, an element that forms strong chemical bonds to
other carbon atoms as well as to many other elements like hydrogen, oxygen,
nitrogen, and the halogens. Because of its versatility in forming covalent bonds, more
than a million carbon compounds are known. The simplest organic compounds are
those composed of only two elements: carbon and hydrogen. These compounds are
called hydrocarbons. Hydrocarbons are organic compounds that contain only carbon
and hydrogen. The four general classes of hydrocarbons are: alkanes, alkenes,
alkynes and arenes. Aromatic compounds derive their names from the fact that many
of these compounds in the early days of discovery were grouped because they were
oils with fragrant odors.

II. Objectives
 To be familiar with the different structures of hydrocarbons
 To be able to construct using models and draw structures of representative
hydrocarbons

III. Materials
 Ball and stick model kit
 Pencil
 Reagents
IV. Procedure

Using the structural patterns for


carbon, draw the Lewis structures Using the structural patterns for
for each of the following alkanes: carbon, draw the Lewis structures
methane, CH4; ethane, CH3CH3; for each of the following alkenes:
propane, CH3CH2CH3; butane, ethene, H2C=CH2; propene,
CH3CH2CH2CH3 and its structural H2C=CHCH3;1- butene,H2C=
isomer; 2-methypropane, CHCH2CH3; cis-2-butene and
CH3CH3CHCH3 trans-2-butene, CH3CH=CHCH3

Using the structural patterns for


Draw the Lewis structure of carbon, draw the Lewis structures
benzene. Each carbon in the ring for each of the following alkynes:
will have the flat arrangement of ethyne, HC≡CH; propyne,
one double bond and two single HC≡CCH3;1- butyne,HC≡
bonds. CCH2CH3; 2-butyne,
CH3CC≡CCH3
V. Data and Results
A. Structure of Alkanes

Alkane Lewis Structure Bond Angle


Methane, CH4 109.5

Ethane, CH3CH3 109.5

Propane, CH3CH2CH3 109.5

Butane, 109.5
CH3CH2CH2CH3

2-methylpropane, 109.5
CH3CH3CHCH3
B. Structure of Alkenes

Alkene Lewis Structure Bond Angle


Ethene, H2C=CH2 120

Propene, H2C=CHCH3 120,120,109.5

1-butene, 120,120,109.5,109.5
H2C=CHCH2CH3

cis-2-butene, 109.5,120,120,109.5
CH3CH=CHCH3

trans-2-butene, 109.5,120,120,109.5
CH3CH=CHCH3
C. Structure of Alkynes

Alkyne Lewis Structure Bond Angle


Ethyne, HCCH 180

Propyne, HCCCH3 180,109.5

1-butyne, 180,109.5
H2CCHCH2CH3

D. Structure of Benzene
Lewis Structure Bond Angle
120
VI. Discussion of Results
Hydrocarbons are the simplest organic compounds. Containing only carbon and
hydrogen, they can be straight-chain, branched chain, or cyclic molecules. Carbon
and hydrogen can unite to make compounds that contain long chains of carbon atoms,
rings, and multiple bonds between two carbon atoms.
Hydrocarbons are classified as either aliphatic or aromatic. Aliphatic hydrocarbons
are divided into three main groups according to the types of bonds they contain;
alkanes, alkenes, and alkynes. On the other hand, aromatic hydrocarbons are
classified as either arenes, which contain a benzene ring as a structural unit or non-
benzenoid aromatic hydrocarbons, which possess special stability but lack a benzene
ring as a structural unit.

Aliphatic Hydrocarbons
A. Alkanes
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 CnH2n+2 and can be classified into three groups; linear straight-
chain alkanes, branched alkanes, and cycloalkanes. Alkanes are the simplest and
least reactive hydrocarbon species containing only carbons and hydrogens. They
are used as the basis for naming majority of organic compounds and they provide
an excellent basis for understanding bonding, conformation, and other important
concepts which can be generalized to more molecules.
They are commercially very important, being the principal constituent of
gasoline and lubricating oils and are extensively employed in organic chemistry
though the role of pure alkanes is delegated mostly to solvents. The distinguishing
feature of an alkane, making it distinct from other compounds that also exclusively
contain carbon and hydrogen, is its lack of unsaturation. That is to say, it contains
no double or triple bonds, which are highly reactive in organic chemistry.

Drawing and naming alkanes:


Each name is composed of two parts, a parent name and a suffix. The
parent name tells us the number of carbon atoms, and the suffix –ane tells us that
the compound is an alkane. For example, hexane tells us that six carbon atoms
are joined by single bonds. To draw a picture of hexane’s structure, join six Cs with
lines which represents the bonds. Every C has four bonds, so every C below must
have four lines.

C C C C C C

The molecular formula for hexane is C6H14, so fourteen H atoms are bonded
to the six carbon atoms. H can form only one bond, so an H is added to the end
of each line above to give the following structure. This applies to all straight-chain
alkanes.

H H H H H H
H C C C C C C H
H H H H H H

or CH3-CH2-CH2-CH2-CH2-CH3 or CH3(CH2)4CH3
But the easiest way to show the structure of hexane is with a skeletal/line
structure. Skeletal structures take advantage of the fact that carbon has four bonds
and hydrogen one. So, all we need do to depict hydrocarbons is to show the
bonding of the carbon atoms. For example, hexane is shown below.
1 3 5

2 4 6

In branched-chains, they are named on the basis of the name of the longest
chain of carbon atoms in the molecule, called the parent. The alkane shown has
three carbons in its longest chain and is therefore named as a derivative of
propane, the unbranched alkane that contains three carbon atoms. The position of
the CH3 (methyl) substituent on the thee-carbon chain is specified by a number 2,
called a locant, obtained by successively numbering the carbons in the parent
chain starting at the end nearer the branch. In this case, both ends would result to
2 as the locant. The compound is therefore called 2-methylpropane.

When dealing with cycloalkanes, it is somehow similar to a skeletal structure


or line formula but instead the two ends will meet forming different shapes. These
are chemical compounds arranged in a form of a ring or a close chain form with
the general formula CnH2n.
For example, cyclohexane. It also has six carbon atoms and 14 hydrogen atoms
but instead of naming it just hexane, cyclo- is added as a prefix indicating that it is
a closed chain.
B. Alkenes
Alkenes are hydrocarbons that contain a carbon-to-carbon double bond.
Like alkanes, alkenes are named with a stem that gives the number of carbon
atoms but with the suffix –ene to indicate a double bond and a number, if
necessary, before the name to indicate the location of the double bond in the
carbon chain.

Drawing and naming alkenes:


Below is an example of propene, just like propane it also has 3 carbon
atoms and 8 hydrogen atoms but there is a presence of a double bond.

In naming branched alkenes, take note of the example below. The counting
of the parent chain started at the end which is closest to the double bond, and that
is a general rule. It is also a general rule to include the number where the double
bond is in the nomenclature. Therefore, the name of the compound below is 4-
methyl-1-hexene.

Same rules apply to cycloalkenes, just need to add the prefix cyclo-. The
name is 4-methyl-1-cyclohexene.
C. Alkynes
Alkynes are hydrocarbons that contain a carbon-to-carbon triple bond. Like
alkenes, alkynes are named with a stem that gives the number of carbon atoms
and with a suffix –yne to indicate a triple bond.

Similar to alkenes, the counting of the parent chain starts at the end closes
to the triple bond and also includes the number where the triple bond is for the
naming. The compound below is named 5-methyl-2-heptyne.

Aromatic Hydrocarbons
A. Benzene
Benzene is an organic chemical compound with the chemical
formula C6H6. The benzene molecule is composed of six carbon atoms joined
in a ring with one hydrogen atom attached to each. As it contains only carbon
and hydrogen atoms, benzene is classed as a hydrocarbon.

Bond Angle
A bond angle is the angle formed between three atoms across at least two bonds
in three dimensional shapes. This is determined by the VSEPR theory. Valence shell
electron pair repulsion (VSEPR) theory is a model used in chemistry to predict the
geometry of individual molecules from the number of electron pairs surrounding their
central atoms.
Questions to Answer
1. How are alkanes, alkenes, and alkynes different?
Alkanes are saturated hydrocarbons meaning there is only a single bond
between the carbon atoms; alkenes are unsaturated hydrocarbons meaning
one or more double bonds between carbon atoms; alkynes are also
unsaturated hydrocarbons with one or more triple bonds between the carbon
atoms.

2. How are aliphatic hydrocarbons different from aromatic hydrocarbons?


Aliphatic hydrocarbons are organic compounds composed of carbon
and hydrogen atoms arranged in straight chains, branched or non-aromatic ring
structures. Aromatic compounds are organic compounds composed of carbon
and hydrogen atoms arranged in ring structures with delocalized pi electrons.

3. How are cyclic hydrocarbons different from aromatic hydrocarbons?


Aromatic Hydrocarbons are especially stable, unsaturated cyclic
compounds made primarily of hydrogen and carbon atoms. Cyclic
hydrocarbons are formed when atoms combine to form a ring. If you break
down the term hydrocarbon, 'hydro-' represents the word hydrogen.

4. What is hybridization and identify the type of hybrid orbitals in alkanes, alkenes,
alkynes, cycloalkanes?
In chemistry, orbital hybridization is the concept of mixing atomic orbitals
into new hybrid orbitals suitable for the pairing of electrons to form chemical
bonds in valence bond theory. In alkane, the carbon is sp3 hybridized as it
requires four degenerate electron orbitals that points in a tetrahedral
arrangement in order to form those four sigma bonds. In alkene, Each carbon
forms 3 sigma bonds and 1 pi bond. And in alkyne Each carbon forms 2 sigma
bonds and 2 pi bonds.
VII. Conclusion
A hydrocarbon is an organic compound made of nothing more than carbons and
hydrogens. It is possible for double or triple bonds to form between carbon atoms and
even for structures, such as rings, to form. Hydrocarbons can be classified as either
aliphatic or aromatic. Aliphatic hydrocarbons are compounds of hydrogen and carbon that
do not contain benzene rings. They also tend to be flammable. There are several types
of aliphatic hydrocarbons and these are alkanes, alkenes, alkynes. Alkanes are linear, or
branching, compounds that are made of varying numbers of carbon atoms that are all
saturated with hydrogen atoms. Alkenes are like alkanes, but they have at least one
double bond between carbon atoms. Alkynes come under the class of unsaturated
hydrocarbons that contains more than one chemical bond. Aromatic hydrocarbons are
stable, unsaturated cyclic compounds made primarily of hydrogen and carbon atoms.
They also have delocalized pi electrons between carbon atoms forming a circle. The
configuration of six carbon atoms in aromatic compounds is known as a benzene ring,
after the simplest possible such hydrocarbon, benzene. Benzene is the most complex
aromatic hydrocarbon, it is an organic chemical compound with the chemical formula
C6H6. As it contains only carbon and hydrogen atoms, benzene is classed as a
hydrocarbon. Molecular geometries can be specified in terms of bond angles. A bond
angle is the angle formed between three atoms across at least two bonds in three
dimensional shapes.

VIII. References
https://en.wikibooks.org/wiki/Organic_Chemistry/Alkanes
https://www.britannica.com/science/hydrocarbon
http://www.4college.co.uk/as/df/shapealk.php

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