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MR. SURRETTE VAN NUYS HIGH SCHOOL CHAPTER 9: ORGANIC COMPOUNDS CLASS NOTES THE CARBON ATOM Of all the elements on the periodic table, carbon forms the strongest bonds, and bonds to the most kinds of atoms. Also, multiple carbon atoms link together with single, double, and triple bonds. The number of carbon-based compounds is many times greater than the sum of all other compounds. ORGANIC CHEMISTRY All life is based on carbon compounds, so the study of carbon is called organic chemistry. However, all “organic compounds” are not derived from plants and animals. STRUCTUAL FORMULAS Structural formulas show the arrangement of atoms in molecules or polyatomic ions. Each dash between two atoms represents a pair of shared electrons. STRUCTUAL FORMULA EXAMPLE The following is the structural formula for propane, one of the simplest organic compounds: SINGLE BONDS Atoms that share two electrons form single bonds. On structural diagrams, single bonds are represented by single dashes between atoms. DOUBLE BONDS Atoms that share four electrons form double bonds. On structural diagrams, double bonds are represented by double dashes between atoms. TRIPLE BONDS Atoms that share six electrons form triple bonds. On structural diagrams, triple bonds are represented by triple dashes between atoms. CARBON BONDING Carbon atoms have hour bonding electrons. The means, on most structural diagrams, C atoms are surrounded by four dashes. HYDROGEN BONDING Hydrogen atoms only have a single electron. This means, on structural diagrams, H atoms have only one dash connecting them to other atoms. CHEMISTRY PAGE 1 MR. SURRETTE VAN NUYS HIGH SCHOOL MOLECULAR FORMULAS Molecular formulas show the actual number and kinds of atoms present in a molecule. PROPANE The structural formula for propane shows 3 axial carbon atoms and 8 peripheral hydrogen atoms. The molecular formula of propane is C3H8. Molecular formulas do not provide as much information as structural formulas. In particular, they do not show how atoms are connected. ISOMERS Several molecules with the same composition but different structures are called isomers. ISOMER EXAMPLE Compare two different compounds that have 4 linked carbon atoms. ISOMERS OF C4H10 C4H10 Although the two compounds above have the same molecular formula, their structural formulas are different in the way that the 4 carbons are assembled. As seen below, structure is just as essential as composition to understanding organic chemistry. C4H10 ISOMERS The two varieties of C4H10 shown are isomers. In other words, they have the same composition but different structures. Structure affects both physical properties and chemical reactivity of isomers. For example, butane boils at -1 oC and isobutane boils at -12 oC. CONDENSED STRUCTURAL FORMULAS Condensed structural formulas leave out some bonds and/or atoms within compounds. The presence of the atoms or bonds is understood. Chemists frequently write condensed structural formulas to omit carbon-hydrogen bonds. CHEMISTRY PAGE 2 MR. SURRETTE VAN NUYS HIGH SCHOOL CONDENSED STRUCTURAL FORMULAS HYDROCARBONS An infinite variety of compounds can be made using only carbon and hydrogen atoms. These compounds are called hydrocarbons. Hydrocarbons are of prime economic importance because they include petroleum and natural gas. ALKANES Propane, butane, and isobutane are all hydrocarbons that contain only single covalent bonds between carbon atoms. These hydrocarbons lack double bonds, triple bonds, and ring structures. As a whole, these types of hydrocarbons are called alkanes. THE SIX SIMPLEST ALKANES ALKENES Alkenes are hydrocarbons that contain at least one double bond between carbons. The simplest alkene is ethylene, C2H4, ETHYLENE CHEMISTRY PAGE 3 MR. SURRETTE VAN NUYS HIGH SCHOOL ALKYNES Alkynes are hydrocarbons that contain a triple bond between carbons. The simplest compound in this class is acetylene, C2H2. ACETYLENE RING STRUCTURES Long chains of carbons can loop around and form closed ring structures. For example, examine the structure of hexane. HEXANE RING STRUCTURES Remove 2 hydrogens on the ends of hexane, and you get cyclohexane. CYCLOHEXANE COMPOUNDS WITH ADDITIONAL ELEMENTS Although all organic compounds contain carbon, and almost all of them contain hydrogen, most of them contain other elements as well. The most common extra elements in organic compounds are oxygen, nitrogen, sulfur, and the halogens (Group 17). HALOGENS Halogens resemble hydrogen because they form single covalent bonds. As a result, halogen atoms can replace any hydrogen atom in hydrocarbons. CHEMISTRY PAGE 4 MR. SURRETTE VAN NUYS HIGH SCHOOL METHANE AND TWO DERIVATIVES ALKYL HALIDES When halogens replace the hydrogen atoms in hydrocarbons, they form compounds called alkyl halides. Alkyl halides include fluorine, chlorine, bromine, iodine, or any combination of these elements. FUNCTIONAL GROUPS Functional groups are specific arrangements of atoms in an organic compound that undergo characteristic chemical reactions. Most organic chemistry is functional-group chemistry. As a matter of fact, organic compounds are even classified according to their functional groups. COMMON FUNCTIONAL GROUPS CHEMISTRY PAGE 5