Carbon Chemistry… The works By: Anushka Rahman Part #1 C a r b o n s… Introduction To understand alkanes and/or alkenes, we will first have to understand their basic origins, and how they were made. For that, we will have to go all the way back to carbons, because carbons are the nominators in all living things. What are carbons? Carbon is an element, on which the molecules of life is based. It has many distinctive properties. It is unique in the variety of molecules which it can form. The chemistry of these molecules forms a separate branch of the subjectORGANIC CHEMISTRY! *booklet given during class… Properties of Carbon… It is a non-mettalic element . It has a valence of four. It has many allotropic forms. It’s atomic number is 6. It is unreactive under normal circumstances. It can be found in the form of coal, graphite, and diamond. *information retrieved from booklet given during class… Fact File… Did you know… Sixth most common element in the world Main, amorphous, graphite and diamond It bonds with itself 6-10 million compounds are known. Not only carbons can be found in allotropes but also in isotopes. Noted from class… Applications Crude oil is used by the petrochemical industry to produce, amongst others, gasoline and kerosene in refineries. Crude oil forms the raw material for many synthetic substances, many of which are collectively called plastics. The isotope carbon-14 was discovered on February 27, 1940 and is used in radiocarbon dating. Diamonds are used as a form if jewelry. Graphite is combined with clay to form the 'lead' used in pencils. * Lutz, Patricia. "Carbon." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Applications…#2 Graphite is also used as a lubricant and a pigment. Diamond is used for decorative purposes, and also as drill bits and other applications making use of its hardness. Coke is used to reduce iron ore into iron. Carbon is added to iron to make steel. Carbon is used as a neutron moderator in nuclear reactors. * Lutz, Patricia. "Carbon." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. How are Carbons related to Alkanes and Alkenes? In alkenes and alkenes, a certain amount of carbon is present. For example, in ethene and ethane, there are two atoms of carbons present. In the same way, carbons are present everywhere. Part #1 H y d r o C a r b o n s… What are hydrocarbons? Hydrocarbons are compounds which consist only of hydrogen and carbons only. Hydrocarbons… Hydrocarbons are part of exothermic reactions. Hydrocarbons can also exist in all stages of matter, and so can the allotropes. Different in structure as well as formulas. It is the simplest form of carbons. Notes from class… Part #2: Alkanes What are Alkanes? Alkanes are chemical compounds that consists of carbon (C) and hydrogen (H). “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Properties of Alkanes Methane melts at -182.5° C (-296.5° F) and boils at -161.5° C (-258.7° F).* The larger the molecule the higher the melting point. Hydrocarbons have low densities, often about 0.8 compared to water, 1.0 Alkanes do not have any functional groups. Alkanes have a low relativity. The more well-structured the molecules are the higher the boiling point. * *Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Fact File Did you know… The parent compound of alkane is methane. The boiling point can almost correlate to its molecular weight. An inconsequential name for alkanes is ‘paraffin’. Functional groups may increase the densities of organic compounds to 1.0. Only a few organic compounds have densities greater than 1.2 . Applications The first four alkanes, Methane, Ethane, Propane, and Butane are used mainly for heating and cooking purposes. Methane and ethane are used in the form of natural gas. Alkanes with a chain length of 35 or more, can be used for road surfacing. An example is bitumen. Propane and butane are used as liquified pertroleum gas, and are also used as propellants in aerosol sprays. Alkanes which are hexadecane and upwards play a major role in fuel oil and lubricating oil. Part #3 Halo Alkanes What are Halo Alkanes? Chemical series of non metals Group seven of the periodic table. These are basically alkanes which also have halogens like chlorine or fluorine in them. Takes place The most widely known group of halogen alkanes are Chlorofluorocarbons (CFCs). (H3C)3C-OH + HCl.H2O → (H3C)3C-Cl + 2 H2O CH3-(CH2)6-OH + SOCl2 → CH3-(CH2)6-Cl + SO2 + HCl. What is an alkyl group? Alkyl group- a functional branch or side chain of carbons. Hydrogen is an atom. Alkyl group is a small molecule. Properties… Halo alkanes are reactive towards nucleophiles. Alkyl alkanes can be synthesized from alkanes, alkenes, or alcohols. Elimination reactions- using hydroxide and alkenes make halo alkenes. 3 types of halogen alkanes: primary, secondary, and tertiary. Primary has one alkyl group other then hydrogen. Secondary has two, tertiary has three. Are inert Break down in the presence of UV rays. Reacts with dry hydrogen. Very reactive Applications… Propellants in aerosol inhalers for drugs used to treat asthma. refrigerants in various home appliances. insulating foams in packaging materials, furniture, bedding, and car seats. Cleaning agents for electronic circuit boards, metal parts, and dry cleaning processes. Effect On The World… CFCs has become a concern which has come to the attention to nearly the whole world. It is rapidly increasing the ‘ozone depletion’ situation, as has added itself to the most hazardous pollutants in the world . Part #4 Alkenes What are Alkenes? Alkenes are unsaturated hydrocarbons, and in the homologous series, they differ by CH2. “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Properties of Alkenes Alkenes are more reactive then alkanes. Alkanes do not conduct electricity. The physical state of alkenes depend on its molecular mass. Alkenes are stable compounds. What is the difference between Alkanes and Alkenes? The difference between alkanes and alkenes is that alkenes are unsaturated, and alkanes are saturated. This has a series of effects on the characteristics and reactions of these elements, and each are different from the other. A Comparison… Alkenes These have unsaturated compounds, which enables it to react with different elements and compounds. This is why it can easily succumb to addition reactions. This makes it extremely useful in the industrial world. Alkanes These have saturated compounds, which means that it cannot, unless forced to, react with other elements and compounds as easily as alkenes. It is useful in the sense that it can be used as a non-reactive component. Fact File… D i d y o u k n o w… The simplest alkene is ethylene. Commonly known as ethene. Alternative names for ‘Alkene’ are ‘Olefin’, or ‘Olefine’. The physical state of both alkenes and alkanes depend on its molecular mass. Hydrocarbons- only contains hydrogen and oxygen atoms. Alkene + water= ethanol Water out of alcohol (dehydrated), can give rise to alkene. Part #5: Al k y n e s What are Alkynes? Alkynes are hydrocarbons that have at least one triple covalent bond between two adjacent carbons. The general formula for the Alkyne is: CnH2n-2. “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Properties of Alkynes It is the third homologous series after alkanes. Alkynes are unstable. Alkynes are very reactive They have triple bonds. Terminal alkynes have one hydrogen atom connected to the carbon on at least one side of the triple bond. Example: Methyl acetylene. Internal alkynes have something other then hydrogen attached to the hybridized carbons, usually another carbon atom. Example: 2-pentyne. Fact File Did you know… Alkynes are usually known as acetylenes, or the acetylene series. Alkynes are involved in many organic reactions. Alkynes have fewer hydrogen atoms in alkanes and alkenes. Applications Alkynes burn in oxygen to give a hot and powerful flame. It is used to weld and cut metal. Acetylene has a melting point of -81° C (-113.8° F) and a boiling point of -57° C (-70.6° F). Dry copper acetylide can be used as an explosive. Acetylene is also used in chemical synthesis. It is used to synthesis vinyl chloride for plastics and synthetic rubber. Part #6: Isomers What are Isomers? 1. chemically identical molecule with different structure: each of two or more molecules that have the same number of atoms but have different chemical structures and therefore different properties 2. nuclide with different energy state: each of two or more nuclides that have the same mass number and atomic number but different energy states and halflives. “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Structural Isomers… Structural isomers are molecules that have the same chemical formula, meaning they have the same atoms in each molecule, but differ in the order in which the atoms are connected. * Wood, James L. "Isomer." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Stereo isomers… 1. Stereo isomers are molecules with the same chemical formula and the same molecular structure, but with their atoms arranged differently within this structure. There are two types of stereo isomers: optical isomers and geometric isomers. Wood, James L. "Isomer." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Optical and Geometric Isomers Optical isomers are the molecules of one isomer will rotate the direction of a beam of plane-polarized light (light that is traveling in the same plane, not in all directions) in the opposite direction that the other isomer will. Geometric isomers are molecules with the same atomic organization (geometry), but with atoms placed at different positions of the molecule’s geometric structure. Wood, James L. "Isomer." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Part #7: Chemical Reactions What is a chemical reaction? A process that changes the molecular composition of a substance by redistributing atoms or groups of atoms without altering the structure of the nuclei of the atoms. “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Substitution… When one element, or molecule, replaces another element by taking it’s place and giving its own to the replaced element or molecule, substitution takes place. H2O + C = CO2 + H (Hydrogen is substituted by Carbon) “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Bromination… To treat or combine a substance with bromine or a bromine compound. Alkene + Bromine = Alkene is brominated “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Hydrogenation… To add hydrogen to a compound in a chemical reaction. O2 + H = H2O (Hydrogen has been added to oxygen to form water.) “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Hydration… A chemical compound containing water molecules that can usually be expelled by heating, without decomposition of the compound. Sunlight + Carbon Dioxide + Water = Glucose + Oxygen “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Dehydration… The process by which a chemical compound loses water molecules or the proportion of hydrogen and oxygen atoms present in water. Sucrose = Carbon + Water C12H22O11(s) = 12C + 11H2O “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Class notes… Fermentation… The breakdown microorganisms. of Many pharmaceuticals fermentation. carbohydrates by are by “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. produced Anaerobic respiration… The production of energy without the presence of oxygen. Anaerobic respiration occurs in some yeasts and bacteria, and in muscle tissue during strenuous exercise when there is insufficient oxygen. “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Oxidation… A chemical reaction in which an oxide forms is called oxidation. S + O2 = SO2 (Sulfur dioxide is formed when oxygen is added to Sulfur) Esterification… To change or make a substance change into an ester. For example, esterification of acetic acid in excess ethanol in the presence of sulfuric acid results in an ester. H3C-COOH + HO-CH2-CH3 → H3C-COOCH2-CH3 + H2O (with the presence of conc. sulfuric acid) “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Notes from class Part #8: Alcohols What is alcohol? Alcohol is an organic compound containing one or more hydroxyl groups bound to carbon atoms. Hydroxyl group- A group of negative ions which are formed by the attachment of an oxygen atom and a hydrogen atom. The Formula of these ions: OH“Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. How is it made? Alcohol is a colorless liquid, and is produced by the fermentation of sugar or starch, which is done by a small single celled fungus named yeast. Formula: C2 H5 OH “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. The facts of manufacture… When sugar is fermented, you get ethanol and carbon dioxide as natural waste products. Ethene + steam = 300 degrees, 60 atmospheres, catalyst-phosphoric acid= ethanol Best temperature for this process is 37. “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Notes from class… Properties… Depending on the number of hydroxyl groups attached to the molecules OH, they are classified in the following ways: Monohydric-one group Dihydric- two groups Trihydric- three groups. “Alcohol." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Properties…#2 They are also a homologous series which are known as alkanols. The simplest alcohol contains one carbon atom and is called methanol. They react with acids to form esters. These are similar to inorganic salt. General formula- CnH2n + 1OH Notes from class… Applications… Beer is made from barley, and contains 4% alcohol Wine contains 8% to 14% alcohol. Ethanol is the only alcohol safe to drink. It is a renewable resource. Notes from class… Part #9: Organic Acids What are organic acids? Carboxylic acids are another homologous series. A common name for organic acids is fatty acids. Formic and acetic acids are the simplest fatty acids. The general formula is CnH2n+1COOH Ethanoic acid is also known as vinegar. Noted from booklet… Properties of Carboxylic Acids -COOH Acid chloride acid anhydrides (you have taken out the hydrogen by another acid group) They are very soluble They are very good solvents They are weak acids They don’t like to dissociate with hydrogen-they don’t make many ions. Notes from class… Applications… They can be used to form esters. e.g. ethanoic acid + ethanol conc. H2SO4=ethyl ethanoate + water Detergents, thickening paints, and lubricants. Stearic acids are also used to combine rubber with other substances, such as pigments. Notes from booklet… Part #10: Esters Esters Esters are organic, often fragrant compounds formed in a reaction between an acid and an alcohol with the elimination of water. Polyester- 70s found in different kinds of plastics. Malleable. Used in clothes. "Esters." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Noted from class… “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Examples of Esters Methyl butanoate Ethyl methanoate Ethyl butanoate Pentyl ethanoate Pentyl butanoate Octyl butanoate Methyl ethanoate Ethyl ethanoate Notes from booklet Properties of Ester Acid Hydrolysis- reaction with water. Acid + alcohol = ester + H2O Ester +H2O = carboxylic acid General reaction= ester + alkali= salt Ester(oil or fat)+ H2O + (strong) alkali = type of salt + alcohol sopanification (making soap) Soap molecules are made of long fatty acid chains. alkanol + alkanoic acid =alkyl alkanoate (ester)+ water Noted from class… “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Part #11: Aldehydes & Ketones Aldehydes Aldehydes have the general formula is ‘R’ represents either a hydrogen atom, or an aliphatic or aromatic group. Aldehydes are used while manufacturing dyes, plastics, and food addictives. Notes from class… Ketones an organic compound containing a carbon atom connected to an oxygen atom by a double bond and to two carbon atoms. The simplest ketone is acetone. CH3-CO-CH3. Are relatively reactive Nitrogen oxide + Hydrocarbon=ketones +/ aldehydes, which are considered as pollution. Noted from class… “Dictionary”Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. "Ketones." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Part #1 2: Aromatic Compounds Aromatic Compounds Are organic compounds that contain one or more rings of carbon atoms and undergo chemical reactions that are characteristic of benzene. About half of all organic compounds are aromatic. They are considered as the most important group of unsaturated cyclic hydrocarbons. The other large group of organic compounds are classified as aliphatic compounds. "Aromatic Compounds." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Some formulas and notes that can help me later… Bibliography 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. http://en.wikipedia.org/wiki/Alkane http://ull.chemistry.uakron.edu/genobc/chapter_11/ http://en.wikipedia.org/wiki/Alkene http://en.wikipedia.org/wiki/Carbon Lutz, Patricia. "Carbon." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. URL:http://members.aol.com/logan20/alkynes.html Encyclopedia information about alkyne The Columbia Electronic Encyclopedia, Sixth Edition Copyright © 2003, Columbia University Press. Licensed from Columbia University Press. All rights reserved. www.cc.columbia.edu/cu/cup/Encyclopedia WordNet information about alkyne WordNet 1.7.1 Copyright © 2001 by Princeton University. All rights reserved. More from WordNet http://en.wikipedia.org/wiki/Alkyne Acetylene." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved. Wood, James L. "Isomer." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Notes from class and home Many definitions taken from ‘Microsoft Dictionary 2006’ http://en.wikipedia.org/wiki/Esterification http://en.wikipedia.org/wiki/Haloalkane "Chlorofluorocarbons." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. “Alcohol." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. "Aromatic Compounds." Microsoft® Encarta® 2006 [DVD]. Redmond, WA: Microsoft Corporation, 2005. Microsoft ® Encarta ® 2006. © 1993-2005 Microsoft Corporation. All rights reserved.