[DOCUMENT TITLE] [Document subtitle] The Carbon Compounds Quarter 2, Weeks 4-6 Overview In your previous lesson, you have learned that non-metals chemically bond to each other by sharing the electrons from their outer shells to attain a stability of eight valence electrons. This process of bonding is what we call covalent bonding. Through the same process, carbon compounds or organic compounds are formed. But what are organic compounds? What does carbon have to do with these compounds? What are the uses of these compounds? In this module, we will tackle the following lessons: 1. The Amazing Super Carbon 2. The League of Organic Compounds At the end of the module, you are expected to: 1. Explain how the structure of carbon atom affects the types of bonds it forms; and 2. Recognize the general classes and uses of organic compounds. Read, discover, and have fun! Pre-Assessment Before you go on further with the module, we must first assess what you already know regarding the lesson. Below is short pre-assessment for you to answer. Encircle the letter of the best answer. 1. Which of the following statements best describe organic compounds? a. Organic compounds are compounds that contain carbon and oxygen only. b. Organic compounds are compounds that are produced by living things. c. Organic compounds are composed mainly of carbon and hydrogen. d. Organic compounds are compounds that contain carbon atoms only. 2. How do carbon atoms form many organic compounds? a. By attracting other elements toward themselves to form the bonds b. By forming many bonds with other carbon atoms and other elements c. By sharing their electrons with other metal and non-metal elements d. By transferring their electrons to the atoms of surrounding elements 3. What is the maximum number of bonds a carbon atom can form? a. 2 c. 4 b. 3 d. 5 4. Emmanuel Juan, a fisher man, went home with some of his catch and told his son to cook the fish. Then his father told him to buy some so that they could start cooking the fish. Which organic compound do you think the boy will buy? a. kerosene c. lubricating oil 1 The Carbon Compounds Quarter 2, Weeks 4-6 b. gasoline d. alcohol 5. Which of the following pairs of organic compounds is highly flammable? a. gasoline, acetone c. lubricating oil, isopropyl alcohol b. water, ethyl alcohol d. liquefied petroleum gas, kerosene 6. Honey is applying something to the ball bearings of the wheels of her bicycle so that friction will be minimized. Which of the following material do you think she is using? a. vinegar c. kerosene b. isopropyl alcohol d. lubricating oil 7. A gasoline boy was being scolded by his store manager for smoking in the vicinity of the gasoline station. Why do you think the manager scolded his employee? a. because gasoline is volatile. b. because gasoline is flammable. c. because gasoline is viscous. d. all of the above. 8. Joimee scratched herself when her arm bumped into the concrete post. What do you think should she apply to make her bruises free from harmful germs? a. formalin c. water b. isopropyl alcohol d. acetone 9. Which organic compound is used as a cleaning agent? a. gasoline c. liquified petroleum gas (LPG) b. kerosene d. ethyl alcohol 10. Which hydrocarbon compound has a triple bond in the molecule? a. octane c. ethene b. methane d. ethyne 11. How many types of bond are there in the following hydrocarbon compound? a. 1 b. 2 c. 3 d. 4 12. To which group of hydrocarbon does the molecule with the structure below belong? a. alkane b. alkyne c. alkene d. none of the above 13. Ethene is a natural gas produced in plants, which acts as a ripening agent of fruits. Which of the following organic compounds has the same ability to ripen fruits? a. butane c. acetylene 2 The Carbon Compounds Quarter 2, Weeks 4-6 b. propene d. pentyne 14. Which alkane will most likely have a very low boiling point? a. propane c. butane b. pentane d. hexane 15. What is the common use of methane? a. disinfectant b. fertilizer c. artificial ripening agent d. fuel 16. Which are true about the use of isopropyl alcohol? I. cleaner II. fuel a. I and II only b. II and III only III. disinfectant IV. fertilizer c. III and IV only d. I and IV only 17. Salvador has to remove the red paint from the paintbrush so that he could still use it again next time. What organic compound should he use? a. acetic acid c. kerosene b. lubricating oil d. formaldehyde 18. Which of the following is a carbonyl compound? a. c. b. d. 19. What organic compound is used by embalmers in treating human cadavers? a. acetic acid c. methyl alcohol b. formaldehyde d. acetone 20. Which compound is an alcohol? a. b. c. d. 3 The Carbon Compounds Quarter 2, Weeks 4-6 LESSON I The Amazing Super Carbon In Biochemistry, we always encounter the element carbon in almost every molecule making up an organism’s body. Afterall, carbon is the most important element to life (aside from oxygen). Why is carbon so basic to life? The reason is carbon’s ability to form stable bonds with many elements, including itself. This property allows carbon to form a huge variety of very large and complex molecules. In fact, there are nearly 10 million carbon-based compounds in living things! Carbon is the sixth element in the periodic table, right in the middle of the first row. The carbon atom has four valence (outermost) electrons. Because of this unique configuration, it is easier for the carbon atom to share its four electrons with another atom or atoms than to lose or gain four electrons. Because each carbon is identical, they all have four valence electrons, so they can easily bond with other carbon atoms to form long chains or rings. In fact, a carbon atom can bond with another carbon atom two or three times to make double and triple covalent bonds between two carbon atoms. Long chains of carbon atoms with double and triple bonds are quite common in biology. Figure 1.The element Carbon in the periodic table. valence electron Figure 2. The atomic structure of carbon. Many molecules contain carbon atoms bonded to each other or to atoms of other elements. These carbon-containing molecules are generally called organic compounds. Organic compounds make up the cells and other structures of organisms and carry out life processes. Carbon is the main element in organic compounds, so carbon is essential to life on Earth. Without carbon, life as we know it could not exist. 4 The Carbon Compounds Quarter 2, Weeks 4-6 Organic chemicals get their diversity from the many different ways carbon can bond to other atoms. The simplest organic chemicals, called hydrocarbons, contain only carbon and hydrogen atoms; the simplest hydrocarbon (called methane) contains a single carbon atom bonded to four hydrogen atoms: Figure 3. methane (CH4) But carbon can bond to other carbon atoms in addition to hydrogen, as illustrated in the molecule ethane below: Figure 4. ethane (C2H6) In fact, the uniqueness of carbon comes from the fact that it can bond to itself in many different ways. Carbon atoms can form long chains: Figure 5. hexane (C6H14) branched chains: Figure 6. isohexane (C6H14) rings: Figure 7. cyclohexane 5 The Carbon Compounds Quarter 2, Weeks 4-6 There appears to be almost no limit to the number of different structures that carbon can form. To add to the complexity of organic chemistry, neighboring carbon atoms can form double and triple bonds in addition to single carbon-carbon bonds: Figure 8. types of simple hydrocarbon bonds Keep in mind that each carbon atom forms four bonds. As the number of bonds between any two carbon atoms increases, the number of hydrogen atoms in the molecule decreases (as can be seen in the figures above). The simplest hydrocarbons are those that contain only carbon and hydrogen. These simple hydrocarbons come in three varieties depending on the type of carboncarbon bonds that occur in the molecule. 1. Alkanes are the first class of simple hydrocarbons and contain only carbon-carbon single bonds. The alkanes are named by combining a prefix that describes the number of carbon atoms in the molecule with the root ending "-ane". The names and prefixes for the first ten alkanes are given in the following table. Carbon Atoms Prefix Alkane Name Chemical Formula Structural Formula 1 Meth Methane CH4 CH4 2 Eth Ethane C2H6 CH3CH3 3 Prop Propane C3H8 CH3CH2CH3 4 But Butane C4H10 CH3CH2CH2CH3 5 Pent Pentane C5H12 CH3CH2CH2CH2CH3 6 Hex Hexane C6H14 ... 7 Hept Heptane C7H16 6 The Carbon Compounds Quarter 2, Weeks 4-6 Carbon Atoms Prefix Alkane Name Chemical Formula 8 Oct Octane C8H18 9 Non Nonane C9H20 10 Dec Decane C10H22 Structural Formula The chemical formula for any alkane is given by the expression CnH2n+2. The structural formula, shown for the first five alkanes in the table, shows each carbon atom and the elements that are attached to it. This structural formula is important when we begin to discuss more complex hydrocarbons. The simple alkanes share many properties in common. All enter into combustion reactions with oxygen to produce carbon dioxide and water vapor. In other words, many alkanes are flammable. This makes them good fuels. For example, methane is the main component of natural gas, and butane is common lighter fluid. 2. The second class of simple hydrocarbons, the alkenes, consists of molecules that contain at least one double-bonded carbon pair. Alkenes follow the same naming convention used for alkanes. A prefix (to describe the number of carbon atoms) is combined with the ending "-ene" to denote an alkene. Ethene, for example is the two-carbon molecule that contains one double bond. The chemical formula for the simple alkenes follows the expression CnH2n. Because one of the carbon pairs is double bonded, simple alkenes have two fewer hydrogen atoms than alkanes. Figure 9. ethene (C2H4) 3. Alkynes are the third class of simple hydrocarbons and are molecules that contain at least one triple-bonded carbon pair. Like the alkanes and alkenes, alkynes are named by combining a prefix with the ending "-yne" to denote the triple bond. The chemical formula for the simple alkynes follows the expression CnH2n-2. Figure 10. ethyne (C2H2) In addition to carbon and hydrogen, hydrocarbons can also contain other elements. In fact, many common groups of atoms can occur within organic molecules, these groups of atoms are called functional groups. One good example is the hydroxyl functional group. The hydroxyl group consists of a single oxygen atom bound to a single hydrogen atom (-OH). The 7 The Carbon Compounds Quarter 2, Weeks 4-6 group of hydrocarbons that contain a hydroxyl functional group is called alcohols. The alcohols are named in a similar fashion to the simple hydrocarbons, a prefix is attached to a root ending (in this case "-anol") that designates the alcohol. The existence of the functional group completely changes the chemical properties of the molecule. Ethane, the two-carbon alkane, is a gas at room temperature; ethanol, the two-carbon alcohol, is a liquid. Figure 11. Ethanol, common drinking alcohol, is the active ingredient in "alcoholic" beverages such as beer and wine. Activity 1 Encircle the letter of the best answer. 1. How many valence electrons does carbon possess? a. 1 c. 3 b. 2 d. 4 2. If two carbon atoms were bonded to each other, what type of bond would exist between the two atoms? a. metallic c. covalent b. ionic d. hydrogen 3. Why is carbon considered as the basic element of life? a. Because it can be bonded to hydrogen. b. Because it is excreted by the body in the form of carbon dioxide. c. Because it is the major component of organic compounds. d. Because it provides fuel for the body. 4. Hydrocarbons are compounds which are mainly made up of carbon and hydrogen atoms. Which of the following is a hydrocarbon with a single bond? a. propane c. pentyne b. butene d. pantene 5. What is the name of the compound below? a. hexane b. 1-octene c. 1-nonyne d. heptane 8 The Carbon Compounds Quarter 2, Weeks 4-6 LESSON 2 The League of Organic Compounds As mentioned earlier, organic compounds are group of compounds that contain the element carbon. Organic compounds contain carbon and hydrogen combined with other elements, namely oxygen, nitrogen, phosphorus, sulfur, and halogens (fluorine, chlorine, bromine, and iodine). Ethyl alcohol, acetone, gasoline, naphthalene, acetic acid, and esters are just a few examples of many useful organic compounds. These kinds of compounds are produced by plants and animals. However, there are also organic compounds that are produced artificially. Liquified petroleum gas (LPG), gasoline, lubricating oil, and kerosene are produced from petroleum. These compounds have different uses in the community. To know more about the uses of some organic compounds, let’s do the activity below. Activity 2 CHECK THE LABEL! Objective: To recognize the common uses of common organic compounds. Materials: Labels or picture of the following products: gasoline, acetone, kerosene, acetic acid, LPG, ethyl alcohol or ethanol. Procedure: Use the label/pictures of the material to answer the following questions. Complete the table by using a check mark (✓) to indicate the uses of the compounds. You may have more than one check mark per sample depending on its use. Uses Gasoline Organic Compounds and Its Uses Acetic Acetone Kerosene LPG Ethanol Acid Beverage Food Antiseptic Fuel Cleaner See the next page for the continuation 9 The Carbon Compounds Quarter 2, Weeks 4-6 Questions: 1. What do you think are the characteristics of the materials which give their uses? __________________________________________________________________ __________________________________________________________________ __________________________________________________________________ __________________________________________________________________ ________________________________________________________________. 2. Why do you think these kinds of organic compounds are very important? __________________________________________________________________ __________________________________________________________________ __________________________________________________________________ __________________________________________________________________ ________________________________________________________________. Properties of Organic Compounds Properties of Organic Compounds Every kind of organic compound has specific properties or characteristics. Although these compounds may show similarities in some properties, these compounds do not have exactly the same properties. Let us take this for example: liquified petroleum gas (LPG), gasoline, lubricating oil, and kerosene are all produced from petroleum. However, each of them is distinct from one another because these compounds vary in one or many properties – odor, viscosity, volatility, and flammability. 1. Odor – it is the smell of the compound. Organic compounds like hydrocarbons mostly smell like gasoline. Alcohols and aldehydes have a pleasant odor; they smell like fruits or flowers. Meanwhile, some variations of carboxylic acid can give you a pungent odor (as that of your armpits). The same goes with amines (which give fishy smell). 2. Viscosity – is a measure of a liquid’s resistance to flow. Some compounds are more viscous or they flow faster. Some compounds are less viscous or they flow slower. 3. Volatility – is the measure of the tendency of a compound to evaporate or turn into gaseous state. 4. Flammability – is the measure of how easily the material burns. Boiling point and phase are also properties given consideration when it comes to hydrocarbons. Look at the table below. What do you notice in the boiling point of the hydrocarbons as the number of carbon atom increases? Why do you think some hydrocarbons are gases and others are liquids? 10 The Carbon Compounds Quarter 2, Weeks 4-6 Figure 12. table of boiling points of alkanes You would notice that as the number of carbon atoms increases in hydrocarbon, the boiling point also increases. This is because the force holding the molecules together increases as the size of the molecule increases. Furthermore, some hydrocarbons are gases because the molecules are small structure and there interaction less among each other, while some hydrocarbons are liquids because the molecules are big structures and there interact more with each other and they tend to settle in liquid state. Now that you have learned about the properties of organic compounds, you will now proceed to the common types of organic compounds. To find out what are these, try doing the activity below. 11 The Carbon Compounds Quarter 2, Weeks 4-6 Activity 3 Common Types of Organic Compounds Before we can learn what these types are, we should know what a functional group is. A functional group dictates the physical and chemical characteristics of an organic molecule. The functional group is a reactive site in an organic molecule, enabling ease of classification and synthesis of numerous organic compounds. The common functional group and its representative structures and family are found below. 1. Alcohol - In chemistry, alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom, which in turn is bound to other hydrogen and/or carbon atoms. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis Figure 13. structure of alcohol 12 The Carbon Compounds Quarter 2, Weeks 4-6 of other compounds, and are among the most abundantly produced organic chemicals in industry. Perhaps the two best-known alcohols are ethanol and methanol (or methyl alcohol). Ethanol is used in toiletries, pharmaceuticals, and fuels, and it is used to sterilize hospital instruments. It is, moreover, the alcohol in alcoholic beverages. Methanol is used as a solvent, as a raw material for the manufacture of formaldehyde and special resins, in special fuels, in antifreeze, and for cleaning metals. Figure 14. applications of alcohol in the Philippines 2. Alkyl Halides - (also known as haloalkanes) are compounds in which one or more hydrogen atoms in an alkane have been replaced by halogen atoms (fluorine, chlorine, bromine or iodine). Alkyl halides are among the most versatile compounds in the chemical industry. Small haloalkanes are some of the most commonly used solvents in chemical laboratories; chlorofluorocarbons have seen widespread use as refrigerants and propellants; and compounds containing both Br and F are often used in fire retardants. Figure 15. tert-butyl bromide, an alkyl halide Figure 16. alkyl halide application in aerosols as propellants 3. Ether - any of a class of organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. Ethers are similar in structure to alcohols, and both ethers and alcohols are similar in structure to water. In an alcohol one hydrogen atom of a water molecule is replaced by an alkyl group, whereas in an ether both hydrogen atoms are replaced by alkyl or aryl Figure 17. diethyl ether 13 The Carbon Compounds Quarter 2, Weeks 4-6 groups. At room temperature, ethers are pleasant-smelling colorless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapors of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers are also important in medicine and pharmacology, especially for use as anesthetics. Figure 18. uses of ether 4. Aldehyde - any of a class of organic compounds in which a carbon atom shares a double bond with an oxygen atom, a single bond with a hydrogen atom, and a single bond with another atom or group of atoms (designated R in general chemical formulas and structure diagrams). Many aldehydes have pleasant odors, and in principle, they are derived from alcohols by dehydrogenation (removal of hydrogen), from which process came the Figure 19. aldehyde name aldehyde. Aldehydes undergo a wide variety of chemical structure reactions, including polymerization. Their combination with other types of molecules produces the so-called aldehyde condensation polymers, which have been used in plastics such as Bakelite and in the laminate tabletop material Formica. Aldehydes are also useful as solvents and perfume ingredients and as intermediates in the production of dyes and pharmaceuticals. Certain aldehydes are involved in physiological processes. Examples are retinal (vitamin A aldehyde), important in human vision, and pyridoxal phosphate, one of the forms of vitamin B6. Glucose and other so-called reducing sugars are aldehydes, as are several natural and synthetic hormones. Figure 20. use of formalin or formaldehyde in preserving deceased bodies 14 The Carbon Compounds Quarter 2, Weeks 4-6 5. Ketone - any of a class of organic compounds characterized by the presence of a carbonyl group in which the carbon atom is covalently bonded to an oxygen atom. The remaining two bonds are to other carbon atoms or hydrocarbon radicals (R). Ketone compounds have important physiological properties. They are found in Figure 21. ketone several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Only a small number of ketones are manufactured on a large scale in industry. They are most widely used as solvents, especially in industries manufacturing explosives, lacquers, paints, and textiles. Ketones are also used in tanning, as preservatives, and in hydraulic fluids. The most important ketone is acetone. Figure 22. commercial acetone 6. Ester - any of a class of organic compounds that react with water to produce alcohols and organic or inorganic acids. Esters derived from carboxylic acids are the most common. The term ester was introduced in the first half of the 19th century by German chemist Leopold Gmelin. Ester is a sweetsmelling substance. Some of them are used as food flavorings Figure 23. ester and other esters are used as fragrances or perfumes. Apart from that, they can be turned into polymers dubbed as polyesters which can be used to make cans or plastic bottles. Figure 24. perfumes made from ester 15 The Carbon Compounds Quarter 2, Weeks 4-6 7. Carboxylic Acid - any of a class of organic compounds in which a carbon (C) atom is bonded to an oxygen (O) atom by a double bond and to a hydroxyl group (―OH) by a single bond. A fourth bond links the carbon atom to a hydrogen (H) atom or to some other univalent combining group. The carboxyl (COOH) group is so-named because of the carbonyl group (C=O) and hydroxyl group. Carboxylic acid derivatives have varied applications. For example, in addition to its use as a disinfectant, formic acid, the simplest carboxylic acid, is employed in textile treatment and as an acid reducing agent. Acetic acid is extensively used in the production of cellulose plastics and esters. Aspirin, the ester of salicylic acid, is prepared from acetic acid. Figure 25. vinegar contains acetic acid, a carboxylic acid 8. Amine and amide - Compounds containing a nitrogen atom bonded in a hydrocarbon framework are classified as amines. Compounds that have a nitrogen atom bonded to one side of a carbonyl group are classified as amides. Amines are used as analgesic, as anesthetic, or even as recreational drug. Amides are used to form resilient products (e.g. nylon). Figure 26. Methamphetamine, an amine, is an illegal drug that causes hallucinations. Figure 27. Kevlar fiber made from amides are used as a raw material for combat clothes. 16 The Carbon Compounds Quarter 2, Weeks 4-6 Activity 4 17 The Carbon Compounds Quarter 2, Weeks 4-6 Pre-Assessment I. Sentence Completion/Word Pool. Pick your answers from the given word pool. 1. _______ as element is present in sample like charcoal, paper and even in a precious stone like 2. _________. 3. ________ compounds are carbon compounds which properties depend on the number of bonds formed. The 4. ________ bonds found in organic or carbon molecules are formed by 5. _________ of electron pairs between atoms. Atoms with four (4) or more valence electrons like carbon form as many bonds as they need electrons to fill their valence shells and thereby reach a stable 6. ______. Cue words: carbon covalent diamond four (4) multiple octet organic sharing three (3) It is important to always count the number of bonds of each particular atom. Carbon should have 7. ______ bonds. Hydrogen has only one (1) bond, oxygen with two (2) bonds, nitrogen could have 8. ________ bonds, and only one (1) bond for halogens. Carbon, oxygen and nitrogen, with more than one bond, could possible formed 9. ___________ bond (double or triple bond). II. Multiple Choice. Choose the best answer. Write the corresponding letter of your choice on the blank provided before each number. ____ 1) Carbon atom forms how many bonds? a. 1 b. 2 c. 3 d. 4 ____ 2) Carbon can bond to ? a. H b. N c. O d. all of these ____ 3) An organic (carbon molecule) bond represents ? a. a transfer of protons c. a pair of shared electrons b. a transfer of electrons d. a pair of shared protons ____ 4) Most organic compounds have (a. lower; b. higher) boiling and melting point as compared to inorganic compound. ____ 5) Which of the following pairs is highly flammable? a. gasoline; acetone c. oil; vinegar b. water; ethanol d. LPG; kerosene ____ 6)Princess wants to remove her nail polish. What must she use? a. gasoline c. ethanol b. vinegar d. acetone ____ 7) Which alkane would likely to have a very low boiling point? a. butane b. hexane c. pentane d. propane 18 1 The Carbon Compounds Quarter 2, Weeks 4-6 ____ 8) What is the common use of methane? a. disinfectant c. fertilizer b. artificial ripening agent d. fuel ____ 9)How many types of bonds are there in the given hydrocarbon compound: a. 1 b. 2 c. 3 d. 4 ____10) To which group of hydrocarbons does the molecule with the structure below? a. alkane b. alkene c. alkyne d. none of these 19 The Carbon Compounds Quarter 2, Weeks 4-6 ANSWER KEY 20