Republic of the Philippines

Region IV-A CALABARZON Department of Education DIVISION OF RIZAL

CASIMIRO A. YNARES SR. MEMORIAL NATIONAL HIGH SCHOOL

Taytay, Rizal

MODULES IN BASIC ORGANIC CHEMISTRY (1st and 2nd GP)

MODULE 1 2 3 4 5 6 7 8 TOPIC The Carbon Atom Organic and Inorganic Compounds The Structural Features Of Organic Compounds Learning to Write Structural Formulas Hydrocarbons Naming Hydrocarbons Other Functional Groups Organic Formulas and Isomerism

IN BASIC BIOCHEMISTRY (3RD and 4th GP)

MODULE 1 2 3 4 5 6 TOPIC Carbohydrates Lipids (Fats, Oils, Waxes ) Proteins Amino Acids Nucleic Acids Vitamins and Minerals

Module 1: Introduction THE NATURE OF ORGANIC COMPOUNDS

The science of organic chemistry deals with the relationship between molecular structure and properties. It is therefore most fitting to begin your study of organic chemistry by considering the common structural features of organic compounds. In order to have a better understanding of molecular structures, you need to review some general chemical ideas especially those involving atomic structure and bonding.

Objectives
At the end of this module, you should be able to: 1. Recognize the existence/ possibility of a great no. of organic compounds and the tremendous diversity in their structures 2. Draw correct Lewis structures; and 3. Identify functional groups and classify organic compounds.

Discussion
Kekule (Germany) and Couper (Scotland) were the first to recognize that carbon is tetravalent it can form four bonds, not only with other atoms (mainly H, O, N) but also with other carbon atoms. The most distinctive feature of carbon atoms is their capacity to form very strong covalent bonds with each other. No other element, including silicon , can do this. Silicon-silicon bonds are easily cleaved. Silicon-oxygen-silicon bonds are quite strong but do not result in the incredible diversity found in carbon compounds. Carbon atoms can link with each other to form linear, branched or cyclic backbones for a wide variety of organic molecules. Take for example only four carbon atoms And see the number of ways by which they can be linked to one another. C C C C C C C C Linear Branched C C C C C Cyclic C C C

You can just imagine how many diverse molecular frameworks can result if there are more carbon atoms that are being linked to one another! Moreover, carbon atoms mat participate in single, double or triple bonds. C C C N C O Single bond C C C N C O double bond C C C N

triple bond

The ability of carbon to form single as well as multiple bonds, not only with another carbon atom, but also with atoms like nitrogen and oxygen, results in greater diversity of molecular frameworks which constitute the skeletons of small and simple molecules or big and complex biochemicals found in living organisms. Organic molecules exhibit isomerisms,a term derived from the Latin iso (equal) and mer (part). There are two general types of isomerism: structural isomerism and stereoisomerism. Structural isomers have the same molecular formula but different structural formulas, i.e., the same atoms can be put together in different ways resulting in different compounds with entirely different properties. For example, two structural formulas can be derived from the molecular formula C2H6O, and each one corresponds to a different compound.

H H C

H C O H H

H C O

H C H

H H Ethyl alcohol Liquid, bp 78.5 0C

H H dimethyl ether gas, bp -23.7 0C

As the number of carbon atoms increases, the number of possible structures corresponding to a molecular formula also increases. If you take a look into Chemical Abstracts, where known organic compounds are catalogued, you will see that there are dozens and sometimes hundreds of different compounds that have the same molecular formula. The four bonds to carbon are directed to the four corners of a regular tetrahedron. As a direct consequence of this, many different three-dimensional structures can arise in organic molecules. This brings us to stereoisomerism (derived from the Greek stereos solid) -a more soluble kind of isomerism which is particularly important in compounds found in living organisms. Stereoisomerism have the same molecular and structural formulas but differ from each other in their three dimensional structures. Take the case of the amino acid alanine, whose structural formula is given below: H H3C C NH2 Alanine COOH

Alanine can have two different three-dimensional structures which are mirror images of each other. CH3 CH3 H H2N COOH L-alanine H HOOC NH2 D- alanine

The two different three-dimensional structures of alanine are related to one another in the same way that our right and left hands are related, thus one is called D alanine (a right-handed molecule) and the other, L- alanine ( a left-handed molecule). Like alanine, most of the molecules that make up plants and animals exhibit handedness. Again, this phenomenon contributes greatly to the existence of a tremendous number of organic compounds. At this point you have probably realized that carbon is indeed very versatile and why it is so. It should now be easy to understand why there are so many organic compounds much more than combined compounds of the rest of the elements in the periodic table. So far we have discussed the common features of organic compounds in terms of their structures. Let us now go to the common behavior of organic compounds as noted in the laboratory. In general, organic compounds, which are largely covalent compounds , have low melting points and limited solubility in water. Some are gases and many are liquids at room temperature; those that are solids melt below 400 0C. In contrast many inorganic salts, which are ionic compounds , melt above 1000 0C. And dissolve readily in water. In addition to the above physical properties, organic compounds are generally combustible (flammable) and/or are sensitive to heat ( decomposed by heat). We observe these properties in everyday life. Hydrocarbons are burned in order to generate heat for cooking and to power motor vehicles. Table sugar (sucrose) is an organic compound which is not combustible but is particularly sensitive to heat. In caramelizing sugar for your leche flan, if you do not carefully control the fire, the sugar immediately decomposes extensively and is turned to carbon.

WORKSHEET 1
Name:_________________________ Year & Sec: _____________________ Date: ________________ Score: _______________

STARTER
Give four reasons for the occurrence of a large number of organic compounds and great diversity in their structures.
1. Carbon can form . . .

2. Carbon atom can link with . . .

3. Carbon has the ability to form . . .

4. Organic molecules exhibit . . .

REINFORCEMENT
Write the correct answer in the space provided in each item. _____________ 1-2. They were the first to recognize that carbon as Tetravalent. _____________ 3. It is where a carbon can be form in four bonds. _____________ 4-7. Carbon atoms can be form with., . . . atom. _____________ 8. Organic molecules which exhibit an equal part. _____________ 9-10 Draw two structural formulas can derived from the molecular formula C2H6O that corresponds to a different compound.

ENRICHMENT
A. Complete the table by writing the general properties organic and inorganic compounds.

Properties Melting point and Boiling point Solubility in polar(water) and non polar solvent Conductivity Flammability and Combustibility Bond

Organic Compound

Inorganic Compound

B. Draw _______ _______ _______ _______ _______ _______

if the substance is organic compound and 1. Methanol, CH30H 2. Sulfuric acid, H2SO4 3. Glucose, C6H12O6 4. Methane, CH4 5. Limestone, CaCO3 6. Baking soda, NaHCO3

if inorganic compound.

CHALLENGE
From the structures given below, choose a pair that would illustrate each of the following (use the letter labels):

C C C DE C C C C GH

C C C C EF C C C C HI

C C C FG

COOH C H OH H3C IJ

HOOC C HO H CH3 JK

COOH C H CH2OH KL H

____ and ____ 1. Ways by which three carbon atoms can link to one another ____ and ____ 2. A pair of structural isomers ____ and ____ 3. A pair of stereoisomers ____ and ____ 4. Molecular frameworks that result from the introduction of a C = C into a linear chain of four carbon atoms