- Introduction - Alkanes Mr. Shields Regents Chemistry U16 L01 1 Organic Chemistry • Organic Chemistry involves the study of Carbon based compounds of which there are millions and many more yet to be made • Much more “diversity” than found in inorganic compounds • What are some examples of Carbon Based compounds? – Petrochemicals – Dyes – Pharmaceuticals - Biochemicals - Polymers - Life 2 Source • The source of almost all organic compounds today is petroleum – Crude oil • Through Synthesis hydrocarbons can be further modified into other organic compounds • Petroleum (crude oil) is first separted into several different categories at refineries • Separation at refineries is a distillation process based on BP (mol. Wt.) 3 Why so many C compounds? • Carbon atoms can bond with other carbon atoms in chains. These bonds are Covalent. • Since Carbon has 4 unpaired electrons it can form 4 covalent bonds. • •C• • 4 Formation of Carbons 4 covalent bonds Carbons ability to form 4 covalent bonds, even with itself, leads to carbons ability to form millions of different compounds, some simple some very complex. 5 Properties of Covalent Substances Covalent compounds are Molecular Compounds • What do we mean by “Molecular” and What kind of properties do they have? Low melting points & boiling points Poor conductors of heat & electricity Solids tend to be soft Can not be worked (not malleable) May be Polar or nonpolar Non-polar is not soluable in water Polar may be slightly sol. to sol. in water Non-polar will dissolve in non-polar solvents React more slowly than ionic compounds 6 Structural Formulas • Shows kind & number of atoms and how they are bonded together. • They are 2-D drawings of 3-D objects so structural formulas aren’t totally realistic. H H–C–H H 7 Structural Formulas • “–” A single line represents one pair of electrons (a single bond). • “=“ A double line represents two pairs of electrons (a double bond). • “” A triple line represents three pairs of electrons (a triple bond). 8 Condensed Structural Formulas • These formulas show kind & number of atoms as well as some information regarding what atoms are joined to what atoms but not how. • They don’t depict bonds Examples: CH4, CH3OH, CH3Cl, CH2Cl2, CH3CH2CH2CH3, CH3COOH No information given on how these oxygen are bonded to this carbon 9 Molecular Formulas • These formulas show kind & number of atoms but not necessarily any other information Condensed Structural formula Examples: CH3OH, CH3CH2CH2CH3, CH3COOH Molecular formula Becomes: CH4O, C4H10, C2H4O2 10 Molecular Shape • When carbon is bonded to 4 other atoms carbon is at the center of a tetrahedron and the 4 other atoms are located at the corners. • This is known As a Tetrahedron If there are 3 C’s Bonded to each other Then there are 3 joined tetrahedrons 11 Vocabulary Interlude • Hydrocarbons: organic compounds containing only Carbon and Hydrogen. – Straight chain: All “internal” C bonded to only 2 other C’s • Ex: c-c-c-c-c-c-c – Branched: One or more int. C bonded to 3 or 4 other C’s • Ex: c-c-c-c-c-c-c-c | | c c c | c-c-c | c 12 Vocabulary • Saturated: organic compounds containing only single bonds (carbon bonded to 4 atoms) • Unsaturated: organic compounds containing one or more double or triple bonds. 13 Vocabulary • Homologous Series: a group of compounds with related structures and properties. – Each member of the series differs from the one before it by the same additional unit. (Ex. The Alkanes; each differs by one -CH2 unit) Ex: CH4 C2H6 C3H8 14 Primary Categories of Hydrocarbons • There are 3 major Hydrocarbon Categories – These can be Straight Chain or Branched • Alkanes (Single Bonds) [hydrogen = 2n +2] – CH3CH2CH2CH3 • Alkenes (Double Bond) [H = 2n] – CH3CH2CH=CH2 • Alkynes (Triple Bond) [H = 2n – 2] – CH3CH2C CH Table Q in your Reference Tables is where you can 15 Get this information! Naming straight-chain Alkanes • All alkane names have the suffix –ane. • The prefix depends on the number of C’s. Ex: Methane Ethane 1 Carbon 2 Carbon What’s the Molecular formula of each? 16 Prefix Meth ane Eth Prop But Pent Hex Hept Oct Non Dec # of C atoms 1 2 3 4 5 6 7 8 9 10 (Check out Table P in your Reference Tables) 17 Alkanes • A Homologous series of saturated hydrocarbons. • Compounds with a related structure differing by the same repeating unit (-CH2-) - General formula is CnH2n+2 (n= no. of carbon atoms) Problem: What’s the molecular formula for the alkane with 27 carbon Formula Name CH4 Methane C2H6 Ethane C3H8 Propane C4H10 Butane C5H12 Pentane C6H14 Hexane C7H16 Heptane 18 Problem: What is the structural formula for pentane? C-C-C-C-C (Shown w/o the Hydrogens) Problem: What is the name of the following Hydrocarbon? CH3-CH2-CH2 Hexane! CH2-CH2-CH3 Is it a branched or straight chain hydrocarbon? 19 Properties of Alkanes • Physical Properties Change systematically with the number of C’s • As the number of C’s In a homologous series increases, the b.p. & m.p. increases. Mol. M.P. Formula CH4 -182 C2H6 -183 C3H8 C4H10 C5H12 C6H14 C7H16 (Due to increasing Intermolecular force C H 8 18 in the form of temporary dipoles) C9H20 -188 -138 -130 -95 -91 -57 -54 B.P. -162 -89 -42 -0.5 36 69 98 126 151 20 SIMPLE HYDROCARBONS • Draw the structural formula, condensed structural formula and molecular formula for the following: – propane – Octane Which should have the highest M.P & B.P.? 21