La Salle University Dasmarias

College of Science and Computer Studies

Physical Science Department

HYDROCARBONS
Research Outline
Prelim Output

Prepared by:
Amoto, Sedreck Anthony D.

Mendoza, Janelle Lorainec A.

Cruz, Renstrel P.

Romasanta, Aradhell B.

Dinglasan, Mary Ann G.

Tolentino, Nalesca Chery Nai G.

Submitted to:
Sir Joseph L. Samonte

Hydrocarbons
I.

Description and discussion of bonding

Hydrocarbons, in organic chemistry, are organic compounds consisting only Carbon and
Hydrogen atoms. These are basically the R in all the other classes of organic compounds.
Hydrocarbons are the simplest classes of organic compounds. They are the foundations of all the
other organic molecules. These compounds, mainly containing carbon and hydrogen, are classified by
their carbon skeletons into saturated and unsaturated hydrocarbons.
Saturated hydrocarbons are hydrocarbons joined by single covalent bonds while unsaturated
hydrocarbons contain multiple bonds either double or triple bonds.

HYDROCARBONS

Apliphatic

Alkane

Alkene

Aromatic

Alkyne

Figure 1.1 Classifications of Hydrocarbons

Hydrocarbons are divided into aliphatic and aromatic groups. Aliphatic have no benzene ring
which is characteristic of the aromatics. Aliphatic are of three types: Alkanes, alkenes, and alkynes.
Alkanes are saturated while alkenes and alkynes are unsaturated.

Alkanes: The Saturated Hydrocarbons

The alkanes are hydrocarbons in which the carbon atoms are all joined by single covalent bonds
in straight, branched or closed chains. Alkanes are also called paraffin. Paraffin means against reaction
in Latin. Alkanes are called paraffin because they are relatively inert and do not readily undergo chemical
reactions under normal conditions. These organic compounds are the most fundamental hydrocarbons
having the general formula CnH2n+2, where n equals the number of carbon atoms found in the molecule.

Table 1 List of commonly used alkane

Alkenes and Alkynes: The Unsaturated Hydrocarbons

Alkenes and alkynes are hydrocarbons containing multiple bonds; while alkynes have at least one
triple bonds joining carbon atoms. Organic compounds containing double and triple bonds are
unsaturated.
Names of alkenes and alkynes are based on the root names of the alkanes with the same
number of carbon atoms. Names of alkenes end in ene. Alkynes end in yne.

Alkenes have the general formula CnH2n. they always have two hydrogen atoms less than their
corresponding alkanes; the general formula of alkynes CnH2n-2. The structures of alkynes are always two
hydrogen atoms less than its corresponding alkenes or four hydrogen atoms less than its corresponding
alkanes.

Cyclic Hydrocarbons
Alkanes, alkenes, and alkynes may form ring or closed chain hydrocarbons. In this case,
they are referred to as cyclic. Cyclic hydrocarbons maybe saturated or unsaturated.

There is another group of cyclic hydrocarbons which is neither saturated nor unsaturated
called aromatic hydrocarbons.
Aromatic hydrocarbons are hydrocarbons containing a ring of six carbon atoms, each
with only one hydrogen atom (or other group) attached. The most common of these aromatics is
benzene.
The structure of benzene is based on overlapping of orbitals. The electrons in the p
orbital, overlap laterally forming pi ( ) bonds that form clouds of electrons above and below
the ring assuming a doughnut shape.

II.

Physical and Chemical Properties

The physical properties of alkenes and alkynes are generally similar to those of alkanes
or cycloalkanes with equal numbers of carbon atoms. Alkynes have higher boiling points than
alkanes or alkenes, because the electric field of an alkyne, with its increased number of weakly
held electrons, is more easily distorted, producing stronger attractive forces between
molecules.

Low melting and boiling points

Boiling points increase the longer the hydrocarbon chain due to increased van der waals
forces.
The longer the chain the more viscous they become.
The longer the chain the smokier the flame is when burnt.
The more branching a chain he's the lower their boiling point, due to less van der waals
forces as molecules can't pack as closely together.
Insoluble in water as they can't hydrogen bond with water molecules.
Flammable, most used as fuels.

Alkanes have relatively predictable physical properties and undergo relatively few chemical
reactions other than combustion; they serve as a basis of comparison for the properties of many
other organic compound families. Alkane molecules are nonpolar, they are insoluble in water,
which is a polar solvent, but are soluble in nonpolar and slightly polar solvents.

Consequently, alkanes themselves are commonly used as solvents for organic substances
of low polarity, such as fats, oils, and waxes. Nearly all alkanes have densities less than 1.0
g/mL and are therefore less dense than water (the density of is 1.00 g/mL at 20C). These
properties explain why oil and grease do not mix with water but rather float on its surface.

Boiling points of alkenes and alkynes

Name

Formula

Ethylene
Acetylene
Propene
Propyne
1-butene
cis-2-butene
trans-2-butene
2-methylpropene
1-butyne
2-butyne
1-pentene
1-pentyne

CH2=CH2
HCCH
CH2=CHCH3
HCCCH3
CH2=CHCH2CH3
cis-CH3CH=CHCH3
trans-CH3CH=CHCH3
CH2=C(CH3)2
HCCCH2CH3
CH3CCCH3
CH2=CHCH2CH2CH3
HCCCH2CH2CH3

Boiling point
(C)
103.7
84.0
47.6
23.2
6.1
+3.7
+0.9
6.6
+8.1
+27.0
+30.2
+40.2

In chemical properties this includes the reactions that hydrocarbons undergo. Saturated
hydrocarbons (alkanes) are not as reactive as other hydrocarbons. It is because they have no double or
triple bonds that can react with acid in order to form carbocations. Alkanes, like most hydrocarbons, can
undergo combustion reactions (burn in the presence of oxygen). Gasoline is an alkane.
As implied above, alkenes are more reactive than alkanes because they can undergo addition
reactions Aromatic hydrocarbons such as toluene is also reactive. They undergo nucleophile aromatic
substitution reactions. There are some tests that can be performed that will help in determining if a
compound is hydrocarbon based on its properties. These are provided below.

Solubility in Water
Hydrocarbons are non-polar. Water is polar. So from like dissolves like you wouldnt
expect any of these three to be very soluble in water. In fact, unsaturated and aromatic
hydrocarbons are slightly soluble in water- the solubility of toluene in water is ~500mg/L not
very much. Cyclohexene is even less than that. Cyclohexane is completely insoluble in water.

Relative Density

Most organic compounds, including hydrocarbons, are less dense than water (density is
less than 1.0 g/mL). So they float on top of water.
Flammability
Most hydrocarbons will burn over a flame- the hydrocarbon reacts with oxygen to
produce carbon dioxide and water. When writing a combustion chemical equation, balance the
oxygen atoms last.

Addition of Bromine (Br2)

As mentioned above, saturated hydrocarbons will only react with bromine under free
radical conditions, meaning you have to add UV light. So simply adding some bromine to
cyclohexane wont cause a reaction to occur. Aromatic hydrocarbons can react with bromine only
in the presence of a strong Lewis acid catalyst such as FeBr 3- youll learn about this next
semester (Carey CH 12.5). So simply adding some bromine to toluene wont cause a reaction to
occur. Cyclohexene will readily react with bromine.

Reaction with Potassium Permanganate (KMnO4)

Potassium permanganate reacts with anything unsaturated. KMnO4 reacts with alkenes
to form vicinal diols. KMnO4 will also react with alkyl benzenes, such as toluene, to form benzoic
acids). Although I dont think any reaction will take place without adding heat. Alkanes wont react
with KMnO4.

Reaction with Sulfuric Acid (H2SO4)

Sulfuric acid reacts with both alkenes and aromatic hydrocarbons, although in different
ways. Sulfuric acid adds to cyclohexene via an acid catalyzed addition. Sulfuric acid adds to
toluene via electrophilic aromatic substitution.

As fundamental as hydrocarbons are to organic chemistry, their properties and chemical

reactions are rather mundane. Most hydrocarbons are nonpolar because of the close electro negativities
of the C and H atoms. As such, they dissolve only sparingly in H 2O and other polar solvents. Small
hydrocarbons, such as methane and ethane, are gases at room temperature, while larger hydrocarbons,
such as hexane and octane, are liquids. Even larger hydrocarbons are solids at room temperature and
have a soft, waxy consistency.
Hydrocarbons are rather unreactive, but they do participate in some classic chemical reactions.
One common reaction is substitution with a halogen atom by combining a hydrocarbon with an elemental
halogen. Light is sometimes used to promote the reaction, such as this one between methane and
chlorine: CH4+Cl2light CH3Cl+HCl.
Halogens can also react with alkenes and alkynes, but the reaction is different. In these cases,
the halogen reacts with the CC double or triple bond and inserts itself onto each C atom involved in the
multiple bonds. This reaction is called an addition reaction. The reaction conditions are usually mild; in
many cases, the halogen reacts spontaneously with an alkene or an alkyne.

Hydrogen can also be added across a multiple bond; this reaction is called a hydrogenation
reaction. In this case, however, the reaction conditions may not be mild; high pressures of H 2 gas may be
necessary. A platinum or palladium catalyst is usually employed to get the reaction to proceed at a
reasonable pace:
CH2=CH2+H2metal catalyst CH3CH3.
By far the most common reaction of hydrocarbons is combustion, which is the combination of a
hydrocarbon with O2 to make CO2 and H2O. The combustion of hydrocarbons is accompanied by a

release of energy and is a primary source of energy production in our society. The combustion reaction
for gasoline, for example, which can be represented by C 8H18, is as follows:

2C8H18 + 25O2 16CO2 + 18H2O + ~5060 kJ

III. Structures
Hydrocarbons are organic compounds consisting of only hydrogen and carbons.
Hydrocarbons takes many forms and strucures but with two main structures. These structures
are called aliphatic hydrocarbons and Aromatic hydrocarbons.

Aliphatic Hydrocarbons
Aliphatic hydrocarbons contain carbon bonds that are joined in a straight line or chains. They
are composed of three groups: Alkanes which are composed of single bond carbons, Alkenes which
contains carbon-carbon double bonds, and Alkynes which is composed of carbon-carbon triple
bond.
Alkanes
Hydrocarbons that are consisting of only single bonds are called alkanes. The carbons
composing alkanes are sp3 hybridized. Methane, ethane, and propane are the alkanes uniquely
defined by their molecular formula.

Alkenes
Hydrocarbons that contain at least one carbon-carbon double bond. The carbons composing
alkenes are either sp3 or sp2 hybridized. Benzene rings are examples of it .

Alkynes
Hydrocarbons containing at least one carbon-carbon triple bond. The carbons composing it
are either sp3, sp2 or sp hybridized.

Aromatic Hydrocarbons
Aromatic hydrocarbons are those containing one or more benzene rings. They are also
generally more stable than what their Lewis structure implies. The "aromatic" in the name was
used to be due to their aromatic smell, but now means a particular sort of delocalized bonding.
Aromatic hydrocarbons are categorized in two namely, arenes which contains benzene rings and
non-benzenoid aromatic carbons which as the name implies doesn't contain a benzen ring.
Arenes
Arenes are aromatic compounds that are composed of benzene rings as a structural unit.
Examples of arenes are naphthalene and toluene.

Nonbenzenoid Aromatic carbons

Nonbenzeoid aromatic carbons are aromatic compounds without benzen rings but are still
strongly stabilized. Examples of nonbenzenoids are cyclobutadiene and cyclooctatetraene.

IV.

Toxicity

Being exposed to hydrocarbons is prevalent today for this component is quite abundant in the
modern society. It is present in different products that are used in daily life basis such as gasoline,
turpentine, furniture polish, household cleansers, propellants, kerosene, and other fuels.
Halogenated hydrocarbons, like carbon tetrachloride, and trichloroethylene, are more likely than
others to be absorbed systemically, leading to varied effects depending on their toxic potential. The
toxicity of hydrocarbons is directly related to their physical properties, specifically the viscosity, volatility,
surface tension, and solubility.

Viscosity refers to the compounds resistance to flow. Substances with a lower viscosity
like gasoline, naphtha and turpentine are associated with a higher chance of aspiration or
inhalation. Toxic potential mainly depends on viscosity Hydrocarbon liquids with low viscosity
(SSU < 60), can spread rapidly over large surface areas and are more likely to cause aspiration
pneumonitis than are hydrocarbons with SSU >60, such as tar.
Volatility refers to the compounds ability to vaporize. Hydrocarbons with a high volatility
can vaporize and displace oxygen, which can lead to a transient state of hypoxia. Not
surprisingly, the degree of volatility is directly related with the risk of aspiration. Simple petroleum
distillates such as kerosene, mineral oil, gasoline, and furniture polish are examples of such
substances that are easily aspirated.
Compounds that are lipophilic are able to cross the blood-brain barrier, leading to CNS effects.
Halogenated hydrocarbons like methylene chloride, chloroform, carbon tetrachloride, and
aromatic hydrocarbons such as benzene, toluene, xylene, are easily absorbed through
respiratory and gastrointestinal mucosa, often leading to CNS toxicity.

Toxicity from hydrocarbon exposure can be thought of as different syndromes, depending on

which organ system is predominately involved. The compounds can be labeled under Acute Toxicity or
Chronic Toxicity depending on the time and way of exposure to the substance. As it was stated above,
hydrocarbons are dangerous and can be toxic if inhaled and it can cause skin and serious eye irritation.
High doses of inhalation of hydrocarbon mixtures can damage the Organ systems that include the
pulmonary, neurologic (headaches, sleepiness, dizziness, nausea, loss of coordination and in extreme
conditions coma and possibly death.), cardiac, gastrointestinal, hepatic, renal, dermatologic, and
hematologic systems. The pulmonary system is the most commonly involved system. It also contains
components that can cause cancer. Types of exposure can be varied by unintentional ingestion,
intentional recreational abuse, unintentional inhalation, and dermal exposure or oral ingestion in a suicide
attempt.

V.

Diseases
The recreational use of inhaling hydrocarbons and other volatile solvents for the purposes of
creating a euphoric state is becoming increasingly common. Several methods are used for this abuse,
including "sniffing" (directly inhaling vapors) that can cause hydrocarbon poisoning, huffing" (placing
a hydrocarbon-saturated rag over the mouth and nose and then inhaling) can cause lung irritation and
neurologic problems, or "bagging" (inhaling via a plastic bag filled with hydrocarbon vapors) can cause
irregular heartbeats or sudden death

Toxicity from hydrocarbon exposure can be thought of as different syndromes, depending on

which organ system is predominately involved. Organ systems that can be affected by hydrocarbons
include the pulmonary, neurologic, cardiac, gastrointestinal, hepatic, renal, dermatologic, and
hematologic systems. The pulmonary system is the most commonly involved system.

Pulmonary
Hydrocarbon pneumonitis is the most common hydrocarbon disease that results from a
direct toxic affect by the hydrocarbon on the lung parenchyma. Swallowed hydrocarbons can enter
and irritate the lungs and can lead to severe pneumonia.
The end result of hydrocarbon aspiration is interstitial inflammation, intra-alveolar hemorrhage
and edema, hyperemia, bronchial necrosis, and vascular necrosis.

Nervous system CNS

CNS toxicity can result from several mechanisms, including direct injury to the brain or
indirectly as a result of severe hypoxia or simple asphyxiation.

Hypoxia occurs when there is no enough oxygen getting to the brain that caused by smoke
inhalation or carbon monoxide poisoning.
Asphyxiation is a condition of severely deficient supply of oxygen to the body that arises from
abnormal breathing. An example of asphyxia is choking.
Long-term exposure to low levels of petroleum hydrocarbons may impair behavior and
memory. Workers like painters and lacquerers employed in occupations involving exposures to
organic solvents suffer deterioration in their emotional balance, memory, intelligence and powers of
concentration.
In addition, for individuals who are huffing or bagging, the act of rebreathing can result in
hypercarbia, which can contribute to decreased level of arousal.
In addition, prolonged exposure to certain hydrocarbons (eg, n -hexane or methyl-n -butyl
ketone) can result in peripheral neuropathy, blurred vision, sensory impairment, muscle atrophy,
and Parkinsonism.

Cardiovascular
Exposure to hydrocarbons can result in cardio toxicity.
Dysrhythmias are a major concern, especially in adolescents. It is an abnormal heart beat:
the rhythm may be irregular in its pacing or the heart rate may be low or high. Halogenated
hydrocarbon abuse can cause a fatal malignant arrhythmia, termed "sudden sniffing death".

Ischemic Heart Disease, also known as Coronary Artery Disease, is a condition that affects
the supply of blood to the heart. Occupational exposure to polycyclic aromatic hydrocarbons (PAH)
is a risk factor for ischemic heart disease. This is cause by the abuse inhaling of hydrocarbons.

Gastrointestinal
Many of the hydrocarbons create a burning sensation because they are irritating to the GI
mucosa. Vomiting has been reported in up to one third of all hydrocarbon exposures. Hepatotoxicity
occurs more frequently with occupational exposure and is less likely to result from inhalant use.
Ingestion can cause direct local injury to the upper GI system (eg. esophagus, stomach,
etc.) which may causes nausea and hematemesis. Halogenated hydrocarbons may cause hepatic
and/or renal tubular necrosis 1-2 days after ingestion.

Acute tubular necrosis (ATN) is often caused by a lack of blood flow and oxygen to the kidney
tissues. It may also occur if the kidney cells are damaged by a poison or harmful substance.

Hepatic
The chlorinated hydrocarbons, in particular carbon tetrachloride, are hepatotoxic. Usually, the
hepatotoxicity results after the hydrocarbon undergoes phase I metabolism, thereby inducing free
radical formation. These free radicals subsequently bond with hepatic macromolecules and
ultimately cause lipid peroxidation. This metabolite creates a covalent bond with the hepatic
macromolecules, thereby initiating lipid peroxidation.
Methylene chloride, a hydrocarbon commonly found in paint remover, is metabolized via the
P450 mixed function oxidase system in the liver to carbon monoxide (CO). Unlike other cases of
CO exposure, with methylene chloride, CO formation can continue for a prolonged period of time.

Renal
Hydrocarbon toxicity can lead to metabolic acidosis, hyperchloremia, and hypokalemia
resulting from distal renal tubular acidosis. Anion gap acidosis occurs as the compounds are
metabolized, and sodium and potassium are lost via renal excretion along with these metabolites.

Distal renal tubular acidosis (Type I RTA) is caused by a defect in the kidney tubes that
causes acid to build up in the blood.

Hematologic

Prolonged exposure to certain aromatic hydrocarbons (especially benzene) can lead to an

increased risk of aplastic anemia, multiple myeloma, and acute myelogenous leukemia. In
addition, hemolysis has been reported following the acute ingestion of various types of
hydrocarbons.

Leukocytosis occurs early in the clinical course of hydrocarbon aspiration unrelated to

pneumonitis and may last as long as one week.
Aplastic anemia is a residue analysis of chlorinated in hydrocarbons in failure of human bone
marrow.
Multiple myeloma causes cancer cells to accumulate in the bone marrow, where they crowd
out healthy blood cells.
Acute myeloid leukemia is a cancer of the myeloid line of blood cells, characterized by the
rapid growth of abnormal white blood cells that accumulate in the bone marrow and interfere
with the production of normal blood cells.

References
Gignos, G. & Angeles D. (2008) Chemistry. Science @ work. Philippines. Neo Asia Punblishing, Inc.
Hydrocarbons. (2016) In Encyclopedia Britannica.
https://www.britannica.com/science/hydrocarbon

Retrieved

Hydrocarbons
Properties.
Retrieved
September
http://www.mendelset.com/articles/689/properties_hydrocarbons
Hydrocarbon. (2016). In Encyclopdia Britannica.
https://www.britannica.com/science/hydrocarbon

Retrieved

September

10,

10,

2016

2016

September

from

from

11,

2016

from

Chemical compound. (2016). In Encyclopdia Britannica. Retrieved September 11, 2016 from
https://www.britannica.com/science/chemical-compound/Functional-groups
Aromatic compound. (2016). In Encyclopdia Britannica. Retrieved September 11, 2016 from
https://www.britannica.com/science/aromatic-compound
Hydrocarbon. (2016). In Encyclopdia Britannica. Retrieved September 11, 2016 ofrom
https://www.britannica.com/science/hydrocarbon/Structure-and-bonding
Hydrocarbon. (2016). In Encyclopdia Britannica. Retrieved September 11, 2016 from
https://www.britannica.com/science/hydrocarbon/Polymerization
Helmenstine, A., Ph.D. (2016, May 23). Helmenstine. Retrieved September 11, 2016, from
http://chemistry.about.com/od/chemistryglossary/g/Aliphatic-Hydrocarbon-Alkene Definition.htm
Alkene.Retrieved September 11, 2016 from https://en.wikipedia.org/wiki/Alkene
Alkyne. Retrieved September 11, 2016 from https://en.wikipedia.org/wiki/Alkyne
Hydrocarbon. Retrieved September 11, 2016 from https://en.wikipedia.org/wiki/Hydrocarbon

Levine, M. D., MD, & Gresham, C., MD, FACEM. (2015, April 21). Hydrocarbons Toxicity (A. Tarabar MD,
Ed.). Retrieved September 11, 2016, from http://emedicine.medscape.com/article/821143overview#showall
Ramnarine, M., MD, FACEP, & Santoriello, L. M., MD. (2015, August 17). Hydrocarbons Toxicity (T. E.
Corden MD, Ed.). Retrieved September 11, 2016, from http://emedicine.medscape.com/article/1010734overview#showall
Grasso, P., & Blok, D. (1986, February). Effects of petroleum hydrocarbons on the nervous system.
Retrieved September 10, 2016, from https://www.concawe.eu/uploads/Modules/Publications/rpt_8651ocr-2004-01279-01-e.pdf
Hydrocarbon
Poisoning.
(n.d.).
Retrieved
September
https://pedclerk.bsd.uchicago.edu/page/hydrocarbon-poisoning

10,

2016,

from

Lewander, W. J., MD, & Aleguas, A., PharmD. (2012, August 6). Hydrocarbon poisoning. Retrieved
September
10,
2016,
from
http://androsma.5gbfree.com/contents/mobipreview.htm?
27/5/27736/abstract/1,26
MedlinePlus - Health Information from the National Library of Medicine. (n.d.). Retrieved September 10,
2016, from https://medlineplus.gov/
Mityanand Ramnarine, MD, FACEP. (2015, August). Hydrocarbons Toxicity. Retrieved September 10,
2016, from http://emedicine.medscape.com/article/1010734-overview#a5