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Module 5 Review of Basic Organic Compounds
Module 5 Review of Basic Organic Compounds
Introduction
Organic chemistry was once thought to be confined to the study of substances produced as
part of the natural processes of living organisms, but as Friedrich Wohler discovered in the early
1800s, organic compounds can be synthesized from minerals and other non-organic materials in
the laboratory. Indeed, modern chemistry and materials sciences have concentrated on the
remarkable properties of carbon atoms for the production of synthetic chemicals, pesticides and a
host of other things. Organic compounds contain carbon, almost always bonded to another carbon
and/or hydrogen.
Organic compounds also contain carbon, along with other elements essential for the
reproduction of living organisms. Carbon is the main factor as it has four electrons that can
accommodate eight electrons in an outer shell. As a result, several forms of bonds can be formed
with other carbon atoms and elements such as hydrogen, oxygen, and nitrogen. Hydrocarbons
and proteins are strong examples of organic molecules capable of producing long chains and
complex structures.
The organic compounds made up of these molecules form the basis for chemical reactions
in plant and animal cells – reactions that provide the energy required to find food, to replicate,
and for all other life-related processes.
2. classify the different organic compounds and describe their general properties;
3. cite applications of some organic compounds and their uses in everyday living, in
the household, in pharmaceutical industry, in food industry, etc.; and
4. explain the effects of some organic compounds to the human body and to the
environment.
Can you imagine how chemists can differentiate each organic compound from all the
others? And how do they name each and every single one of them?
⮚ Structural formula gives you excellent ways to describe and visualize the bonds in an
organic molecule. It shows all the dashes that represent carbon-carbon bonds, carbon-
hydrogen bonds, as well as the bonds between carbon and other elements.
Organic chemistry was once thought to be confined to the study of substances produced as
part of the natural processes of living organisms, but as Friedrich Wohler discovered in the early
1800s, organic compounds can be synthesized from minerals and other non-organic materials in
the laboratory. Indeed, modern chemistry and materials sciences have concentrated on the
remarkable properties of carbon atoms for the production of synthetic chemicals, pesticides and a
host of other things. Organic compounds contain carbon, almost always bonded to another carbon
and/or hydrogen.
Sometimes, other elements, such as phosphorus, nitrogen and oxygen, are also bound to
carbons. There are a few carbon compounds that are not considered organic molecules. Those
involve carbon dioxide, carbon monoxide, cyanates, cyanides and other carbon-containing ion
compounds.
Alcohols include chemicals such as ethanol and isopropanol. They are used as antiseptics
and ethanol is a staple of the beverage industry. Also, carboxylic acids include a wide range of
chemicals, including pharmaceuticals. Aspirin, one of the oldest commercial medicines, contains
carboxylic acid.
While there are millions of organic compounds, there is a fairly simple classification
scheme for these compounds and a method for naming even the most complex organic
compounds. This unit will focus on helping you to identify the classification of organic
compounds and to name only some of the most common of these compounds.
Hydrocarbons
Organic molecules that contain only carbon and hydrogen are called hydrocarbons. They
react readily with oxygen to produce carbon dioxide and water, releasing energy and light in the
process. Hydrocarbons are nonpolar molecules, as such they are poor conductors of heat and
electricity, have a low density, have a low boiling and melting points, and do not dissolve in
water.
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The carbon atoms in a hydrocarbon can form single, double or triple bonds. They can also
make straight chains, branched chains or rings. These different bonds and bond patterns allow
carbon and hydrogen to form a wide variety of compounds. Hydrocarbons may be classified
according to the bond between carbon atoms. These are alkanes, alkenes and alkynes.
2 - Methylbutane
Alkanes are often described as saturated hydrocarbons. This means that they have
carbon skeletons that are filled to capacity with hydrogen atoms. Alkanes always contain the
greatest possible number of hydrogen atoms for their number of carbon atoms. Table 5.1 gives
the prefixes, number of carbon atoms, names, molecular formula and condensed formula of the
first ten straight chain alkanes.
Did you notice something similar in the names of alkanes given above? The names of these
compounds all end in the suffix –ane. This is in accordance to the International Union of Pure
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and Applied Chemistry (IUPAC) system of labeling. The root part of an alkane’s name gives its
number of carbon atoms as in Table 5.1. For example, meth- means 1 carbon atom, eth- means
2 carbon atoms, prop- means 3 carbon atoms and so on.
Alkenes and alkynes are the other two types of hydrocarbons. Both are classified as
unsaturated hydrocarbons because they contain at least one double bond or triple bond
between carbon atoms. Alkenes are unsaturated hydrocarbons that contain at least one double
bond and have a general formula of CnH2n, and have 2 fewer hydrogen atoms than alkanes.
Alkynes are unsaturated hydrocarbons that contain at least one triple bond and have a general
formula of CnH2n - 2. In naming the compounds, alkenes end in –ene and alkynes end in –yne.
Eth-
Prop-
But-
More hydrocarbons exist in longer chains, branch chains or rings. In fact several classes of
organic compounds can be derived from hydrocarbons. These organic compounds are called
hydrocarbon derivatives because they can be derived from basic hydrocarbons. Hydrocarbon
derivatives are molecules that contain carbon and hydrogen atoms as do hydrocarbons, but
contain additional atoms or group of atoms. This group of organic compounds is further classified
based on the presence of structural features called functional groups.
There are a number of recurring types of structural features in organic compounds that
commonly are known as functional groups. In fact, a traditional approach to the subject of
organic chemistry involves the classification of compounds according to their functional groups.
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Thus the structural features C=C, C≡C, C=O, OH, NH 2, and C≡N are the functional groups of
alkenes, alkynes, carbonyl compounds, alcohols, amines, and nitriles, respectively. It will be
helpful to look at the structural features of some of the major types of organic compounds even
though the details of their chemistry will not be discussed further. Examples of the structures
arranged in accord with their functional groups are given in Table 5.3. The examples chosen are
representative of compounds containing carbon and hydrogen (hydrocarbons) as well as
compounds containing halogens, oxygen, nitrogen, and sulfur. We do not expect you to memorize
this table. In time you will become familiar with all of the types of structures in it.
In Table 5.1 we generally have used systematic names as first-choice names because
these names emphasize the relationships between the compounds and ease the burden of the
beginning student in having to remember many special names. We have little hope that
systematic names such as methanal, 2-propanone, and ethanoic acid soon will replace the
commonly used nonsystematic names formaldehyde, acetone, and acetic acid. But there is no
question that every organic chemist knows what compounds the names methanal, 2-propanone,
and ethanoic acid represent.
CH2=CH2
Alkene C=C CnH2n
Ethane
CHCH
Alkyne C=C CnH2n-2
ethyne
CH3Cl
Halocarbon -F, -Cl, -Br, -I R–X
chloromethane
CH3CH2OH
Alcohol -OH R – OH
ethanol
CH3OCH2CH3
Ether -O- R – O – R’
methoxyethane
CH3CH2C – H
-C– R–C–H
II
Aldehyde II II
O
O O
propanal
CH3 – C – CH3
-C– R – C – R’
II
Ketone II II
O
O O
propanone
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CH3CH2C – OH
- C – OH R – C – OH
II
Carboxylic Acid II II
O
O O
propanoic acid
CH3CH2C – O – CH3
-C–O– R – C – OR’
II
Ester II II
O
O O
methyl propanoate
CH3CH2CH2NH2
Amine - NH2 R – NH2
propanamine
CH3CH2C – NH2
- C – NH2 R – C – NH2
II
Amide II II
O
O O
propanamide
Hydrocarbons are a set of organic compounds. Its molecules are composed of carbon and
hydrogen atoms, organized in different structures depending on the type of hydrocarbon.
For the most part, hydrocarbons come from oil. This is because oil is the result of the
decomposition of organic matter and therefore offers a large amount and concentration of carbon
and hydrogen.
Petroleum derivatives, that is, hydrocarbons, are involved in many industries, from aeronautics
to the toy industry. Almost all the fuels used in transportation are derived from hydrocarbons,
which are used to create polluting waste (carbon dioxide). Therefore, it is currently trying to
replace them with other types of fuels and energy sources.
The hydrocarbons are processed to manufacture all kinds of plastics, acrylics, nylon,
gloves, paints, synthetic fibers, containers, adhesives, insecticides, detergents, refrigerants and
fertilizers
Halocarbons
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a hydrocarbon, a halocarbon is formed. The general formula for a halocarbon is R – X, where R
symbolizes the hydrocarbon, and X stands for the halogen atom. The X may represent fluorine,
chlorine, bromine or iodine. Most halocarbons are nonpolar, with low boiling point and are
insoluble in water but are soluble in hydrocarbon solvents.
To name a halocarbon, first name the hydrocarbon portion of the molecule, then add a
prefix to indicate the halogen atoms.
Example of halocarbon
Trichlorofluoromethane Dichlorodifluoromethane
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Fig. 4 Biodegradability period of halocarbons
Alcohols
When a hydroxyl group, or –OH group, replaces one or more hydrogen atoms in a
hydrocarbon, an alcohol is formed. The general formula for an alcohol is R – OH where R
symbolizes the hydrocarbon and OH represents the hydroxyl group. The –OH is the functional
groups in alcohols.
Alcohols can be classified as primary, secondary or tertiary based on the position of the
hydroxyl group, as shown in Figure 5. Primary alcohols have hydroxyl group attached to only one
carbon usually the terminal carbon atom. Secondary alcohols have hydroxyl group attached to
the carbinol carbon with another carbon attached to it. Tertiary alcohols have hydroxyl group
attached to the carbinol carbon with another two carbon atoms attached to it.
Ethers
An ether molecule contains an oxygen atom bonded to two carbon atoms. The general
formula is R – O – R’, where R and R’ (read as R prime) are hydrocarbon chains. The – O – is the
functional group on an ether molecule.
The oxygen atom in a molecule of ether creates a slightly polar region. This makes small
ether molecules soluble in water. However, longer nonpolar hydrocarbon chains in larger ether
molecules decrease polarity, making them less soluble in water. Ethers have lower boiling points
than the corresponding alcohols but higher than the corresponding hydrocarbons.
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The IUPAC name of an ether gives the suffix –oxy to the smaller hydrocarbon chain
bonded to the central oxygen atom. For example, in the condensed formula
CH3CH2OCH2CH2CH3, two hydrocarbon chains are bonded to oxygen. The smaller chain has two
carbon atoms, thus the root is ethoxy. The other chain retains its hydrocarbon name, propane.
The compound is known as ethyxypropane. Common names may also be used to name ethers.
After you have located the oxygen atom, name the attached hydrocarbon chains just as you
would name a branch chain by using –yl suffix for each. Then add the word ether. Therefore,
ethoxypropane could be called ethyl propyl ether.
Ethers are organic compounds with a sweet smell at room temperature. They are
colourless and evaporate quickly when exposed to air. It is flammable and hence catches fire very
easily and therefore should be handled with care. Being flammable and volatile it is used in cold
weather to start a diesel or petrol engine. It is also used as a refrigerant.
Fig. 7. Ether as anesthesia people go to sleep or become unconscious during surgery. The
discovery of ether allowed physicians to use more refined techniques of surgery and medications.
They got a better idea of human physiology. But due to the flammable nature of ether, it has now
been replaced with safer alternatives. Since diethyl ether can be used as an anaesthetic, it is an
appealing recreational drug. It is basically a controlled substance and can be inhaled by the
users to induce euphoria and sedation. But overdose of diethyl ether can cause respiratory
paralysis and also result in death.
Aldehydes
Aldehydes are more polar than hydrocarbons because of the carbonyl group. But they do
not form hydrogen bonds as alcohols do. Their melting and boiling points are higher than the
corresponding hydrocarbons but lower than the corresponding alcohols.
To name an aldehyde according to IUPAC, add the suffix –al to the root name of the
parent hydrocarbon. For example, CH3CH2CH2CHO is named butanal because it has four
carbon atoms.
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Fig. 8 Examples of aldehyde
Ketones
Ketones also have carbonyl group. A ketone molecule has a carbonyl group in the interiror
of a hydrocarbon chain. Its general formula is R – COR’. Ketones have several properties similar
to aldehydes. The melting and boiling points of ketones are higher than the corresponding
hydrocarbons but lower than the corresponding alcohols. These too maybe explained by the
presence of their functional group, the carbonyl unit. Acetone is named from the root of the
hydrocarbon using the suffix –one. A number prefix is necessary to indicate the position of the
carbonyl group. For example, the compound shown below:
2 – propanone
2 -
butanone
Dimethyl ketone
ethyl methyl ketone
Acetone
Fig. 9 Examples of ketone compounds
Carboxylic Acids
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Carboxylic acids are identified by the presence of carboxyl group. A carboxyl group (-
COOH) is one in which a carbon atom is connected to a hydroxyl group with a single bond and
to an oxygen atom with a double bond. The general formula for a carboxylic acid is R – COOH.
Carboxylic acids are also called organic acids.
Carboxylic acids are polar due to the carboxyl group. This makes them soluble in water.
Also, they can form intermolecular hydrogen bonds. As such, their boiling points are higher than
hydrocarbons with a similar molecular mass. Table 5.4 shows some examples of foods containing
carboxylic acids.
Acid (Common
Food Formula
Name)
In naming carboxylic acids, the suffix –oic and the word acid are added to the root name
of the parent hydrocarbon chain. A simple 7-carbon carboxylic acid is named heptanoic acid.
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manufacturing of wine. It is also used as a food preservative and in settings of gel or
jellies.
Esters
Esters have the carboxyl group and hydrocarbon group. The general formula for an ester is
R – COOR’. It can be formed from a reaction of a carboxylic acid and an alcohol. The boiling
points of esters are lower than those of alcohols or acids having comparable molar masses. This
is because esters do not intermolecular hydrogen bonds, although they are polar. Esters have
distinctive odors that depend on the alcohol and acid from which they are synthesized. Fruity
odors, with aroma of bananas and pineapples, are characteristic of esters. Figure 12 shows
example of fruits rich in ester.
Esters are named for the acid and alcohol from which they are produced. The name of the
alcohol is given first with the suffix changed to –yl. . next the name of the acid is given with the
suffix changed to –oate. For example, an ester formed from propanol and butanoic acid is
referred to as propyl butanoate. Some more examples are given in Table 5.5.
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Methanol Butanoic acid Methyl butanoate Apple
Amines
Amines have boiling points higher than their corresponding hydrocarbons but lower than
that of the corresponding alcohol. This is because the amino is polar, though not as polar as the
hydroxyl group of alcohol.
In naming amines, the suffix –amine is added to the root name of the hydrocarbon.
CH3CH2CH2CH2NH2 is called butanamine because the chain is butane. Amines are also given
common names. The hydrocarbon chain is named a branch chain with the suffix –yl plus the
suffix amine. Thus, the butanamine is also known as butylamine.
Amides
An amide contains an amino group attached to the carbon atom of a carboxyl group. This
group of organic compounds is formed by the reaction of amines with carboxylic acids. The
general formula for an amide is R – CONH2.
Like amines, amides are also important biological molecules. Proteins are formed by
amino acids linked together by an amide bond called the peptide bond. Nylon is synthetic
polyamide fiber containing an amide. Simple amides can also be recognized by their distinctive
smell, which is responsible for the odor of mice.
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Amides are named by adding the suffix –amide to the root name of the hydrocarbon. The
parent chain of the hydrocarbon depends upon the carboxylic acid from which the amide is
formed. For example, CH3CH2CONH2 is named propanamide because it is derived from
propanoic acid.
Things made from the use of organic molecules utilizing the applications and principles of
organic chemistry are all around us in our daily lives. For example, nylon, PVC, and
polyethylene are important polymers made out of organic compounds. Also, soaps, detergents,
and sanitizers are some other examples of daily use organic compounds used for cleaning and
disinfection purposes.
Organic compounds constitute not only the building blocks of living organisms but also
various metabolic processes ranging from keeping us alive to the maintenance of or life in
general.
Specifically, organic compounds essential to living organisms are carbohydrates, fats and
lipids, proteins and nucleic acids. Let us explore a little of some of these:
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Carbohydrates are the instant and major
source of energy for almost all of the living
organisms. These molecules are primarily made up
of atoms of carbon, hydrogen and oxygen with the
ratio or hydrogen to oxygen being the same as
present in water molecule. Besides energy sources,
some carbohydrates are also involved in providing
structural integrity.
the form of small droplets in special cells called adipose cells in animals and serve as energy
stores as mentioned earlier. Upon need, these fat molecules are broken down to release the
energy needed for the cell.
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Just like lipids, the most important function of proteins is in the formation of cell
membranes as essential structural and building blocks of them. As parts of the cell membrane,
they are also involved in various signaling processes of the cell. The existence of all living beings
depends on proteins. Besides being structural parts of the membranes, proteins are also
suspended in the cytoplasm of the cells thereby performing their respective vital roles ranging
from cell growth, survival to cell death. Also, proteins serve as strengthening and supporting
materials in the tissues, e.g., bones, muscles, cartilage, and tendons all are composed of proteins.
Nucleic acids are complex organic molecules composed of a carbohydrate ring, a nitrogen
containing molecule (nitrogenous base) and a phosphate group. Like proteins, nucleic acids are
also complex and large molecules. There are two basic types of nucleic acids present in the living
systems – DNA (deoxyribonucleic acid) and RNA (ribonucleic acids). The importance of the
nucleic acids lies in the very fact that they constitute the genetic material of living organisms
and without them, life cannot be imagined.
Nowadays, food industry does not only rely on the non-processed stuffs but also use
chemical either to enhance the flavor or appearance. The following are some of the important
organic compounds in food industry.
Many health association of various countries suggest food industry to use organic color
additive as it is safer for human health. Some of the most famous color additive for food are
carotenoids for yellow, orange, and deep red derived from carrot, potato, and pumpkin and
chlorophyll from plants’ leaves for green color.
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Fig. 20 Functions of organic compounds in food industry
Another important organic compound in food industry is crop fertilizer as shown in Figure
21. Many foods are result of processed natural source such as crops, vegetables, fruits, seeds, and
many more. In order to increase the production, farmer needs fertilizer. Synthetic fertilizer sells
better but organic fertilizer is safer as well as less costly. Basically any living being that contains
nutrient needed such as nitrogen, potassium, ammonium nitrate and the like can be fertilizer.
Farmers can take it from animal feces, seaweeds, fish extracts and many more.
Food emulsifier is of importance to combine water and oil element of the food materials as
the two naturally will not mix together. Emulsifier helps to make a more various food that
combines ingredients from both water and oil based. Organic emulsifier derived from organic
compounds are milk, phospholipids chemicals, sorbitan, sodium, and eggs. In facts, many
emulsifier are from natural sources as they blend with the food better with almost no unpleasant
after taste.
In order to prevent food to oxidize too fast, it will need antioxidant. Antioxidant help to
slow oxidation within the ingredients of the food and keep the nutrient inside. The most popular
organic compound as antioxidant is vitamin C or ascorbic acid and vitamin E or tocopherol.
If food lovers ever wonder why noodle, bread, pasta can swell just by heat, there is a food
additive called bulking agent. Bulking agent in bakery usually use baking soda. But most foods
that can swell use starchy based chemical additive such as amylum.
Lactic acid is another important organic compound that is generated from natural source
such as milk. The lactic acid has various role and crucial one as it has many benefit in food
processing. It helps to assist fermentation to produce yogurt, cheese, soy sauce meat product and
many more. Surely, these products are very popular and needed by human.
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References:
Matthews, C.K. and Van Holde K.E. 1996. Biochemistry. 2nd Ed. The Benjamin Cummings
Publishing Company Inc. New York
Morrison, R.T. and Boyd, R. N. 2004. Organic Chemistry. 6 th Ed.Prentice Hall International
Editions, New Jersey.
Sylianco, C.Y. 2006. Principles of Organic Chemistry
www.scienceaide.net
www.chemlibretexts.net
www.slideserve.com
www.science-online.com
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