M2W4

General
Chemistry
I
Organic Compounds
I. Learning Competencies/ Objectives

II. Lesson Proper

A. Introduction:

ORGANIC COMPOUNDS ARE CARBON-CONTAINING SUBSTANCES. THEY FORM

COVALENT BONDS-THOSE THAT CONTAIN ONLY SINGLE BONDS ARE SAID TO BE
SATURATED; THOSE WITH DOUBLE AND TRIPLE BONDS ARE UNSATURATED.

Organic molecules contain a nonspecific part designated R- (for alkyl compounds) or Ar- (for
aromatic compounds), plus a specific part called a functional group.
There are two major classes of organic compounds: the hydrocarbons and the hydrocarbon
derivatives.

B. Discussion:

Hydrocarbons
Hydrocarbons are the simplest organic compounds, containing only carbon and hydrogen.
Hydrocarbons can be classified further into four series of compounds: alkanes, alkenes, alkynes, and
aromatic hydrocarbons.
Table 9.1. Classes of hydrocarbons
Class Type Formula* Bond Type -ending Examples Name of
Compound
Alkane CnH2n+2 Saturated- -ane CH3-CH3 Ethane
single bond
Alkene CnH2n Unsaturated- -ene CH2=CH2 Ethane
double bond
Alkyne CnH2n-2 Unsaturated- -yne HC≡CH Ethyne
triple bond
Aromatic aromatic C6H6 Benzene
*n is the number of carbon atoms.
The alkane series is described as saturated because all the carbon atoms utilize single bonds.
Compared to alkenes and alkynes, alkanes have the most number of hydrogen atoms. Alkanes are
generally inert and stable. One of the few reactions they undergo is combustion in the presence of oxygen.
The major sources of alkanes are crude oil or petroleum, and natural gas.
When the carbon-to-carbon bonds are double bonds, a new homologous series, the alkene, is
formed. The number of hydrogen atoms in an alkene is twice the number of carbon atoms. Alkenes are
described as unsaturated because they contain less than the maximum amount of hydrogen that can be
bonded to the carbon framework. Generally, alkenes are more reactive than alkanes. Alkenes can be
converted to alkanes by hydrogenation, the process of reducing or saturating organic compounds in the
presence of a catalyst, which can be nickel, palladium, or platinum. Hydrogenation is used in the
manufacture of lard.
Alkynes contain at least one triple bond. They are also unsaturated, and are more reactive than
alkanes. The simplest alkyne is acetylene, which is widely used in acetylene torches for welding
purposes, and as raw material for the manufacture of synthetic rubber.
The fourth class of organic compounds characterized by the presence of a benzene ring is called
aromatic hydrocarbons. Benzene has six carbon atoms joined by alternating single and double bonds. It
is stabilized by resonance, i.e., two or more valid structures can be drawn for s molecule. Benzene is used
in the synthesis of nylon and polystyrene but its use has diminished in recent years because of its
carcinogenic (cancer-inducing) properties. Aromatic hydrocarbons come mainly from coal.
In the early 19th century, most substances that were isolated from natural sources contained a
benzene ring and had a fragrant odor. Thus, they were categorized as aromatic because of their pleasant
aroma. Today, many substances have the benzene ring, but are not fragrant. Still, the term “aromatic”
persists.

Hydrocarbon Derivatives without the Carbonyl Carbon

Organic halides are of the type formula R-X, where R is an aliphatic or aromatic compound
and X is a halogen (Cl, Br, I).organic halides are used as solvents in households and industry. Carbon
Tetrachloride (CCl4) was a common household solvent until it was banned for its toxicity and
carcinogenic effects. Chloroform (CHCl3) was used as an anesthetic. Chlorofluorocarbons (CFCS), e.g.,
Freon-12 (CF2CL2) were used as propellant and refrigerant gas, but they were replaced because they are
harmful to the ozone layer.
1. Alcohols of the type formula ROH (where R is an aliphatic group) are common and have any
practical uses. Ethanol (C2H5OH) and is isopropyl alcohol are used as disinfectants. Alcohols are
the most versatile of all organic compounds because they can be converted to other families of
compounds.
2. Phenols of the type formula ArOH i.e., an –OH bonded to a benzene ring are industrially
important in the manufacture of dyes and plastics.
3. Ethers of the type formula ROR’ are commercially important as nonpolar solvents.
4. Amines of the type formula RNH2 are present in many compounds with biological activity:
epinephrine, a hormone; niacin, a vitamin; the stimulants nicotine, amphetamine, and cocaine;
and in amino acids, proteins, and nucleotides such as deoxyribonucleic acid (DNA).

Hydrocarbon Derivatives with the Carbonyl Carbon

These hydrocarbon derivatives are incorporated with the carbonyl functional group. The carbon
atom of this group has two remaining bonds that may be occupied by hydrogen, alkyl or aryl substituents.
If at least one of these substituents is hydrogen, the compound is an aldehyde. The derivatives of this
group are:
1. Aldehydes of the type formula RCHO, where R is either an alkyl or an aromatic group, e.g.,
acetaldehyde, CH3CHO.
O
║
C

2. Ketones of the type formula RCOR’, where the H of an aldehyde is replaced another R group
,e.g., acetone or dimethyl ketone.
Aldehydes and ketones usually have appealing tastes and fragrances. They are often used as
flavoring in food and candies, or as fragrance in inhalants and perfumes. The simplest aldehyde,
 formaldehyde (CH2O), is used as a “pickling” solution for biological specimens. Acetone, (CH 3)2
C=O, is used as solvents for removing nail polish and marker ink.
3. Carboxylic acids of the type formula RCOOH. Acetic acid, CH3COOH, is the acid in vinegar.
Carboxylic acids with long carbon chains are usually solids at room temperature. They are called
fatty acids and may either be saturated or unsaturated.
Examples are

a) Lauric acid (12C, saturated) CH3(CH2)10COOH

b) Palmitic acid (16C, saturated) CH3(CH2)14COOH
c) Linoleic acid (16C, saturated) CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH

4. Esters of the type formula RCOOR’ gives pears, bananas, oranges, and apples a pleasant and
fruity odor.

5. Aminides of the type formula RC-NH2 are formed by the reaction of organic acids with amines.
The peptide bonds found in proteins are special amide bonds.

Table 9.2. Summary of hydrocarbon derivatives and type formulas

Hydrocarbon Derivatives Type Formulas
Organic Halides R-X or Ar-X
Alcohols ROH
Phenols Ar-OH
Ethers ROR’
Amines RNH2
Aldehydes RCHO
Ketones RCOR’
Carboxylic Acids RCOOH or ArCOOH
Esters RCOOR’
Amides RCONH2

Structural Isomerism
Isomers are molecules of the same molecular formula, but of different arrangement of atoms.
Different types of isomerism include chain isomerism, position isomerism, and functional group
isomerism.
Chain Isomerism arises because of the possibility of branching in carbon chains. For example,
butane (C4H10), has two isomers. In one of the isomers, the carbon atoms are arranged in a “straight
chain”; in other butane isomer, the chain is branched:

a) Straight-chain isomer
CH3-CH2-CH2-CH3
b) Branched isomer
CH3
│
CH3-CH-CH3
Example 1: Pentane (C5H12) has three isomers:
1. CH3–CH2–CH2–CH2–CH3
CH3
│
2. CH3 - C - CH3
│
CH3
CH3
│
3. CH3–CH2–CH–CH3

In position isomerism, the basic carbon skeleton is unchanged, whereas the important groups are
moved around. For example, the molecular formula C3H7Br has 2 structural isomers. One of the
molecular formulas has bromine lying at the end of the chain, but on another isomer, it is found in the
middle.
Another type of structural isomerism is functional group isomerism in which isomers have
different functional groups, and thus, the isomers belong to different compound families. For instance, the
molecular formula C3H6O could be propanal or propanone.

Example 2: The molecular formula C3H6O2 has structural isomers which include propanoic acid and
methyl ethanoate.

Some Reactions of Organic Compound

Some of the reactions of organic compounds include combustion reactions, hydrolysis, and
addition reactions.
Combustion reactions are rapid reactions that produce a flame. The chemical reaction below
shows the combustion of propane, which is a gas used for cooking.
C3H8 + 5O2 → 3CO2 + 4H2O
Hydrolysis is the splitting of a substance as it reacts with water. One type of hydrolysis reaction
is the formation of soap which is saponification. Saponification is the process of using fats and sodium
hydroxide solution to produce soap. Soap is a mixture of sodium salts of long-chain carboxylic acids
produced by the splitting of ester molecule to carboxylic acid and alcohol.

Additional reactions are reactions wherein two or more molecules combine to form a larger
molecule. Addition reactions involve chemical compounds with multiple bonds such as alkenes and
alkynes.

Example 1: Addition of chlorine to ethylene to form ethylene chloride

Example 2: Addition of a hydrogen molecule to ethane (in the presence of platinum) to form ethane
CH3CH3

C. Practice:
D. Summary:

E. Extended Work:

F. Assignment:

III. Additional Resources