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Grade 11 Unit 8 SCIENCE 1108 CARBON CHEMISTRY: HYDROCARBONS CONTENTS I. II. CARBON COMPOUNDS . . . . . . . . . . . . . . . . . . . . . . . . . 2 Classification of Organic Compounds . . . . . . . . . . . . . 2 Sources of Organic Compounds . . . . . . . . . . . . . . . . . . 5 CARBON ATOMS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10 Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10 Forms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11 Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 III. HYDROGEN AND CARBON . . . . . . . . . . . . . . . . . . . . . . 17 Saturated Hydrocarbons . . . . . . . . . . . . . . . . . . . . . . . . 18 Unsaturated Hydrocarbons . . . . . . . . . . . . . . . . . . . . . . 23 Author: Editor: Illustrators: Harold Wengert, Ed.D. Alan Christopherson, M.S. Alpha Omega Graphics 804 N. 2nd Ave. E., Rock Rapids, IA 51246-1759 © MM by Alpha Omega Publications, Inc. All rights reserved. LIFEPAC is a registered trademark of Alpha Omega Publications, Inc. All trademarks and/or service marks referenced in this material are the property of their respective owners. Alpha Omega Publications, Inc. makes no claim of ownership to any trademarks and/or service marks other than their own and their affiliates’, and makes no claim of affiliation to any companies whose trademarks may be listed in this material, other than their own. CARBON CHEMISTRY: HYDROCARBONS Our Creator in His wisdom made a universe that is unique. No length of time nor combination of circumstances could have produced such a world as ours. The study of carbon chemistry is truly a study of God’s creation. You will learn that the uniqueness of the carbon atom is the basis of all life. The choice of this atom with its designed characteristics is indeed a mark of an omnipotent Creator. No work of chance could have happened upon the combination necessary to produce life. David proclaimed in Psalm 19:1, “The heavens declare the glory of God and the firmament sheweth his handywork.” Science LlFEPACs 1108 and 1109 will be a study of the carbon atom and the chemistry of life. The study of functional groups of organic compounds will help you to see the glory of God in creation. In this LIFEPAC® you will review the atomic nature of carbon and the molecular structure of carbon compounds. You will also learn more about hydrocarbons, their sources, and their chemistry. For anyone interested in medicine, nursing, biology or chemistry as a career, these two LlFEPACs should be of special interest. OBJECTIVES Read these objectives. The objectives tell-you what you will be able to do when you have successfully completed this LIFEPAC. When you have finished this LIFEPAC, you should be able to: 1. 2. 3. 4. 5. 6. 7. Classify compounds as organic or inorganic. Identify the three major sources of organic compounds. Describe the structure of the carbon atom. Identify and to describe the three forms of carbon. Describe carbon bonding. Classify alkanes, alkenes, and alkynes. Describe alkanes, alkenes, and alkynes. Survey the LIFEPAC. Ask yourself some questions about this study. Write your questions here. ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ ____________________________________________________________________________________________ 1 I. CARBON COMPOUNDS Carbon compounds are a part of the familiar carbon cycle. The carbon cycle was part of God’s natural balancing of nature. At the time of the Flood, nearly all of our coal and petroleum resources were buried and formed. These carbon compounds are the basis of all the synthetic plastics and petrochemicals man has made for his comfort, as well as his main source of fuel. In this section you will study the sources and classification of carbon compounds. SECTION OBJECTIVES Review these objectives. When you have completed this section, you should be able to: 1. 2. Classify compounds as organic or inorganic. Identify the three major sources of organic compounds. CLASSIFICATION OF ORGANIC COMPOUNDS All substances can be classified into either of two categories, organic and inorganic. This classification scheme was used by the early chemists in a slightly different manner than it is being used today. Originally, the term organic was used in its general sense in that rocks and minerals are inorganic; but plants, animals, and the substances they produce are organic. In this sense, the adjective organic tells you that a substance is, or has at one time been, a part of a living organism. An organic substance according to this classification scheme is derived from things that are, or have been, alive. Early definition. This system of classification was set up because prior to the year 1800, organic substances were believed to contain a “vital spirit.” Since no chemist possessed, nor could ever hope to attain, a “bottle of vital spirit,” laboratory production (except by living things) of organic compounds was believed to be impossible. Thus two separate and distinct types of substances were thought to 2 meaning in chemistry today. To illustrate, study the following exercises with special attention to the products of these reactions. A student did the following experiment to collect the data for your study. One sugar cube (sucrose) was added to a 100 ml beaker. Enough concentrated H2SO4 (HIGHLY CAUSTIC) was added to soak the cube completely (about 2 ml). The mixture was allowed to set for several minutes. One of the products of the reaction was a gas which he was able to detect by condensing it on the surface of a cool watch glass set on top of the beaker. The liquid was tested with cobalt chloride paper (detects H2O) and the paper turned colors. A solid residue product of the reaction resembled charred wood or carbon. The reaction became hot. exist: organic substances, which were impossible to synthesize, and inorganic substances, which could be synthesized. Therefore, originally organic chemistry was founded as the study of compounds from living things that contained a vital spirit” (acquintessance). Historians of science refer to this theory as the Theory of Vitalism. Considerable doubt had begun to cloud this theory when in 1928, the German chemist Friedrich Wohler synthesized urea, a compound normally produced by animal metabolism. While working with the inorganic compound ammonium cyanate, he surprisingly discovered crystals of urea in his beakers. Since then, thousands of organic compounds have been synthesized, and the Theory of Vitalism has passed into oblivion. Modern definition. The terms organic chemistry or organic compound have a slightly different Do these activities. 1.1 On the basis of the student’s data and observations, complete these activities. a. What does concentrated H2SO4 do to sucrose? Complete the equation for this reaction. C12H22O11 + 11 H2SO4 → 12 __________ + 11 H2SO4 + 11 __________ b. Is the concentrated H2SO4 a catalyst in this reaction? __________ c. Explain your answer in b. _______________________________________________________________ ___________________________________________________________________________________________ d. What was the gaseous product of this reaction? ___________________ e. Did the reactants give off energy when they formed the products? ___________________ f. Is the reaction exothermic or endothermic? ___________________ g. Do the products or the reactants have more enthalpy? ___________________ h. On the basis of these observations, complete the following diagram. 3 1.2 What is urea? _______________________________________________________________________ _____________________________________________________________________________________ 1.3 Describe the Theory of Vitalism. ______________________________________________________ _____________________________________________________________________________________ _____________________________________________________________________________________ 1.4 Descirbe Friedrich Wohler’s contribution to science. ____________________________________ _____________________________________________________________________________________ _____________________________________________________________________________________ _____________________________________________________________________________________ ment carbon. Examination of the compounds from living things shows an abundance of this element. Organic chemistry is the study of compounds made of carbon. Many compounds of this element, although not products of living things, are classified as organic compounds. Exceptions to the rule are oxides of carbon (CO and CO2), metal carbonates, and metal cyanides. All of these exceptions are considered to be inorganic compounds. Many plastic materials burn and leave a charred, black residue like that of the H2SO4-sugar reaction. The products of the preceding reaction are similar to the results of leaving bread in the toaster or meat and potatoes in the oven too long. A hot flatiron left on a piece of cloth yields the same charred products. Sugar, plastics, food, and cloth are part of a large group of substances which have two things in common: (a) they all contain organic compounds and (b) they all contain the ele- Do this activity. 1.5 The following circle represents all chemical compounds. Crosshatch organic compounds vertically and inorganic compounds horizontally on the drawing. All Organic Compounds Compounds of Living Things All Inorganic Compounds Write true or false. 1.6 ___________ Compounds of carbon are organic. 1.7 ___________ Organic compounds can not be synthesized. 4 SOURCES OF ORGANIC COMPOUNDS Since Vitalism is dead, what is so special about compounds of carbon that they should be studied separately from the compounds of the other hundred or so elements? In part, the answer seems to be that so many carbon compounds exist. About 50,000 compounds of all the elements other than carbon are known to exist. Well over a million organic compounds are known, and every year more than 100,000 new organic compounds are produced. Carbon atoms can attach themselves to one another to an extent not possible for atoms of any other element. Carbon atoms can form chains thousands of atoms long or rings of all sizes, such as chains made of paper clips or strings of popcorn. The chains and rings can have branches and cross-links with atoms of other elements (chiefly hydrogen) attached to the carbon atoms. Each different arrangement of atoms corresponds to a different compound, and each compound has its own physical and chemical properties. Therefore, the order in which atoms are attached to each other and the electrons which hold them together are very important in accounting for the properties of compounds. Structural formulas and wood models representing molecules can be used to account for the physical and chemical properties of compounds. What is significant about carbon that it forms so many compounds? Man himself is a walking organic chemical machine. The intricate balance between life and death, learning and forgetting, growing or not growing, fighting disease or becoming sick is organic in nature. Any student of medicine or nursing will certainly need to understand and appreciate the beauty of this branch of chemistry. The delicate balance of nature has its foundation in the study of organic chemistry. Much of our modern day technology and pollution, especially ecological, is organic in nature. Not only is organic chemistry contemporary, but it is also a clue to the past. Much of the history 5 of the earth and the study of petrology involves the study of the world of carbon. For example, natural gas, petroleum, and coal are the largest sources of carbon compounds. Although many of these materials are used as they are, many compounds from these sources are used as raw materials for synthesizing new compounds. Coal, for example, has become such an important source of medicines that some are advocating developing atomic energy more rapidly and saving our coal reserves. Industry makes use of the wide range of boiling points of compounds in petroleum to separate crude oil into gasoline, kerosene, fuel oil, and lubricating oil. Complete the last two hydrocarbons in the chart below. Crude oil is heated in a large distilling apparatus. The fraction which boils off between 40° to 206°C is collected and sold as gasoline. Petroleum. Natural gas is about 90 percent methane (CH4) with some ethane (C2H6) and propane (C3H8) in it. Natural gas is found in certain porous rock formations. Natural gas is used for heating buildings, for cooking food, and for a starting compound to produce other organic substances. Methane, ethane, and propane are colorless and are practically odorless. By law, a sulfurcontaining compound with a distinctive odor must be added to natural gas before it is distributed for commercial consumption. The addition of these substances immediately warns people of the danger of a gas leak, and they can take safety precautions to prevent a fire or explosion. Petroleum is a primary source of hydrocarbons. Hydrocarbons are organic compounds composed of two and only two elements, namely hydrogen and carbon. The simplest family of hydrocarbons is the alkanes. Table 1: Fractions of Petroleum Fraction Distillation Temperature C° Carbon Number Percent Crude Oil Below 20° C1 - C4 2% Petroleum ether 20 - 60° C5 - C6 Ligroin 60 - 100° C6 - C7 2% Gasoline 40 - 206° C5 - C10 32% Kerosene 175 - 325° C12 - C18 18% Fuel oil Above 275° C12 and higher 20% Lubricating oil Nonvolatile liquids long chains Asphalt Nonvolatile solids polycyclic structures Natural gas Coal. The carbon content ranges from 50 to 90 percent in peat, lignite, bituminous coal, and anthracite. Soft, or bituminous, coal contains less pure carbon than hard coal, or anthracite. If the impurities in soft coal are volatile, and if soft coal is heated in the absence of sufficient air to burn 6 completely to CO2 and H2O, large amounts of pollution occur from the C, CO, and unburned hydrocarbons. Industrial cities that power their plants with low-grade soft coal have especially large amounts of pollution from the incomplete combustion of the soft coal. When coal is heated to a high temperature in the absence of air, it undergoes decomposition. Volatile products (coal gas and coal tar) distill off and a residue called coke remains. The coke is a valuable industrial material which finds its chief use in the reduction of iron ore (iron oxide) to iron for the manufacture of steel. Coke is essentially carbon that still contains the mineral substances that are present in all coals (and form the ash that results when coal or coke is burned). About eight gallons of coal tar are obtained from a ton of coal. It is a very complex mixture; over two hundred different carbon compounds have been isolated from coal tars. Although the great value of coal to mankind has been as a fuel, a source of energy, the many substances in coal gas and coal tar make coal also an important source of chemical raw materials. Plant and animal products. Plants and animals are themselves highly effective chemical factories and they synthesize many carbon compounds useful to man. These useful products include sugars, starches, plant oils and waxes, fats, gelatin, dyes, drugs, and fibers. Wood is a primary product of plant (tree) life. This organic product is useful to the building trades, to the paper industry, and as a source of heat energy for heating and cooking. This product is again gaining prominence in home use for heating and cooking. As natural gas supplies diminish and become more expensive, wood will regain importance in home use. Complete these statements. 1.8 Well over ______________ different organic compounds are known to exist. 1.9 Each year over ______________ new organic compounds are produced. 1.10 Carbon atoms can form chains ______________ of atoms long. 1.11 A major source of today’s medicines is ______________ . 1.12 Hydrocarbons contain only the elements of a. ____________________________ and b. ____________________________ . 1.13 The chemicals added to natural gas to give the gas an odor is ______________ . 1.14 Natural gas contains the organic compounds of a. ____________________ , b. ____________________ , and c. ____________________ . 1.15 The alkanes in gasoline include a. ____________________ , b. ____________________ , c. ____________________ d. ____________________ , e. ____________________ , and f. ____________________ . 1.16 The residue of coal decomposition that is used in the manufacture of steel is called ______________ . 1.17 Three uses for wood include a. ____________________________ , b. ____________________________ , and c. ____________________________ . 1.18 A major problem associated with the incomplete combustion of soft coal is ______________ . 1.19 Gasoline is that distillation fraction that has a boiling point range of a. ______________ to b. ______________ °C . 7 Write true or false. 1.20 ___________ There are many more inorganic than organic compounds. 1.21 ___________ Carbon chains can form branches and cross-links. 1.22 ___________ Man is an organic being. 1.23 ___________ The balance of nature has its foundation in the study of organic chemistry. Balance this equation. 1.24 The manufacture of steel is a very important process. Complete this equation by balancing it.. _______ Fe2O3 + _______ C →_______ Fe + _______ CO2 Do these activities. 1.25 Arrange these alkanes in order of increasing boiling point: CH4, C6H14 , C2H6, C13H28 , C10H22 a. ____________________ (lowest boiling point) b. ____________________ c. ____________________ d. ____________________ e. ____________________ (highest boiling point) 1.26 As the number of carbons in the hydrocarbon increases, the boiling point ___________________ . Adult check ___________________ Initial Date Review the material in this section in preparation for the Self Test. The Self Test will check your mastery of this particular section. The items missed on this Self Test will indicate specific areas where restudy is needed for mastery. SELF TEST 1 Answer true or false (each answer, 1 point). 1.01 ___________ All carbon compounds are organic compounds. 1.02 ___________ All organic compounds are products of living things. 1.03 ___________ Organic compounds are carbon compounds. 1.04 ___________ Carbon compounds that are organic are products of living things. 1.05 ___________ One organic compound is CO2. 1.06 ___________ Ammonia, NH3, is an organic compound. 1.07 ___________ Methane, CH4, is an organic compound. 8 Match these items (each answer, 2 points). 1.08 _______ number of different organic compounds a. pollution 1.09 _______ major source of medicine b. coke 1.010 _______ major problem in burning soft coal c. 1.011 _______ residue of coal decomposition d. coal 1.012 _______ first organic compound synthesized e. urea f. 100,000 1,000,000 Complete these statements (each answer, 3 points). 1.013 Three uses for wood include a. ______________________ , b. ______________________ , and c. ______________________ . 1.014 Carbon atoms can form chains ______________________ of atoms long. 1.015 Hydrocarbons contain only the elements of a. ____________________ and b. ____________________ . 1.016 The three major sources of organic compounds are a. ______________________ , b. ______________________ , and c. ______________________ . Balance these equations (each answer, 2 points). 1.017 a. _______ CH4 1.018 1.019 + b. _______ O2 → c. _______ CO2 + d. _______ H2O a. _______ Fe2O3 + b. _______ C → c. _______ Fe + d. _______ CO2 a. _______ C b. _______ O2 → c. _______ CO + Arrange these compounds (each answer, 2 points). Arrange the following alkanes in order of increasing boiling point: C20H42 , C16H34 , C2H6 , C150H302 , C11H24 , C32H66 , C9H20. 1.020 ____________________ 1.021 ____________________ 1.022 ____________________ 1.023 ____________________ 1.024 ____________________ 1.025 ____________________ 1.026 ____________________ (lowest boiling point) (highest boiling point) 64 Score 80 Adult Check _______________ ___________________ Initial 9 Date