ALKANES, ALKENES, ALKYNES, AND AROMATIC HYDROCARBONS Molecular formula: CHq C2Hs H d ' ry Expanded structural formula:H —C -C-C-y ! ie H 4H oH Condensed structural formula: CH3— CH2 — CH3 Isomers: same molecular formula but different Bek Goons Gio 2 CoHeo 35 CsHi2 3 CioHa2 75 CoHia 5 CisHa2 4347 Gis 9 CooHaa 336 319 GHis 18 CagHe2 4111 846 763 Substituent — an atom or group of atoms attached to a chain ( or ring ) of carbon atoms Akyl group — group of atoms that would be obtained by removing a hydrogen atom from an kane, CH; = methane CHs = methyl ( akyl group ) Propyl group - CH2— CHz ~ CHs ( attaches through an end carbon) Isopropyl group - attaches through the middle carbon - gf =CHs CHs Cycloalkanes ranging from 3 — 30 are found in nature. Cyclopentane and hexane are especially abundant in nature Isomerism in Cycloalkanes — possible for cycloalkanes that contain 4+ carbons - cycloalkanes restrict “free” rotation for the carbon atoms in the ring - alkanes have free rotation about all carbon-carbon bonds RCH ns ae po iPHYSICAL & CHEMICAL PROPERTIES OF ALKANES & CYCLOALKANES 1.) Alkanes and cycloalkanes are insoluble in water - C-—H bonds are nonpolar bonds, hydrocarbons are nonpolar compounds - Water is polar 2.) Density is less than water appx: 0.6 g/ml - 0.8 g/mL. 3.) Boiling Point increases with an increase in carbon chain length or ring size = appx increases 30°C for every carbon atom added to the chain - short continuous chains (1-4) are gases at room temp - 5-17 are liquid ~ 18+ are solids at room temp - branching on a carbon chain LOWERS the BP of an alkane - branched alkanes are more compact, with smaller surface areas than their straight — chain isomers - _cycloalkanes have higher BP than their noncyclic counterparts with the same number of carbon atoms - cyclic systems are more rigid and more symmetrical cyclopropane and cyclobutane are gases at room temp - _cyclopentane — cyclooctane are liquids at room temp CHEMICAL PROPERTIES OF ALKANES & CYCLOALKANES - alkanes are the least reactive type of organic compounds - alkanes readily undergo combustion with oxygen - products are always energy, C02 & HzO UNSATURATED HYDROCARBONS - hydrocarbons that contain one or more C-C multiple bonds: double, triple or both - alkenes, alkynes, and aromatic hydrocarbons ~ have physical properties similar to those of saturated hydrocarbons ~ chemical properties are MUCH different - chemically more reactive due to the presence of the C-C multiple bond(s) - multiple bonds serve as locations where chemical reactions occur - whenever a specific portion of a molecule governs its chemical properties, that portion of the molecule is called a functional group = Functional Group — is the part of a molecule where most of its chemical reactions occur - C-C multiple bonds are the functional group for an unsaturated hydrocarbonCHARACTERISTICS OF ALKENES AND CYCLOALKENES: - alkenes and cycloalkanes are isomeric with each other due to the loss of 2 hydrogens + CH=CH, CH=CH - CH (IUPAC = ethene) (IUPAC = propene) common name = ethylene common name = propylene Isomerism in Alkenes: potential for structural isomers is greater for alkenes than alkanes, because there is more than one location where the = can be placed in systems containing 4 or more carbons 4= carbon alkane 4 = carbon alkenes (two isomers) (3 isomers) oe =) c=c-c-c Cl-bo C-C -c-C 1 butane ¢-c=c-c (a-butene) i c=ac-c =—e- i coe z a- Metyppopane a-methyl- I- propene PHYSICAL & CHEMICAL PROPERTIES OF ALKENES: PHYSICAL: - generally insoluble in water - soluble in nonpolar solvents - densities lower than that of water - MP is usually lower than that of the alkane with the same number of carbon atoms - Alkenes with 2-4 carbon atoms are gases at room temperature - Unsubstituted alkenes with 5-17 carbons and 1 = are liquids - Those with still more carbons are solid at room temp CHEMICAL: - flammable - undergo combustion with products of CO2, H20 and energy - aside from combustion, almost all other reactions of alkenes take place at the CC double bondPHYSICAL & CHEMICAL PROPERTIES OF ALKYNES: - physical properties of alkynes are similar to those of alkenes and alkanes - generally insoluble in water, soluble in organic np solvents, low densities, and have a BP that increases with molecular mass low molecular mass alkynes are gases at room temp CHEMICAL — similar to alkenes AROMATIC HYDROCARBONS. PROPERTIES: 1.) 6 membered ring of carbon atoms in which all C-C bonds are identical 2.) Each carbon only has 1 hydrogen attached to it, with all hydrogen atoms equivalent to one another 3.) MF = CeHe indicating a high degree of unsaturation because of the low hydrogen to carbon ratio 4.) Chemical reactivity is different from that normally associated with an unsaturated compound. 1865 German chemist August Kekule’ proposed a cyclic, alternating single - double bond structure for benzene PROPERTIES: - generally resemble other hydrocarbon properties - insoluble in water, good solvents for other np materials - less dense than water