Organic Chemistry Objectives: 1.state general properties and describe some reactions of organic compounds 2.describe the bonding between atoms in molecules of organic compounds 3.compare general formulas of several hydrocarbon series and apply IUPAC system in naming their members 4.State names, structural formulas, and uses for members of several types of hydrocarbon derivatives Created By C. Ippolito Dec 2006

Organic Chemistry originally defined as the study of c cc carbon compounds present in living organisms produced by living organisms now is expanded to include carbon compounds produced from inorganic compound synthesized outside of living things Created By C. Ippolito Dec 2006

Inorganic Carbon Compounds carbon monoxide – CO carbon dioxide - CO 2 compounds containing carbonate ions – CO 3 2- bicarbonate ions – HCO 3 - cyanide ions – CN - Created By C. Ippolito Dec 2006

Organic Carbon Compounds fossil fuels oil, natural gas, coal synthetic materials made from fossil fuels plastics, nylons, polyesters, resins “living” compounds carbohydrates lipids proteins nucleic acids Created By C. Ippolito Dec 2006

Organic vs. Inorganic Properties Hexane – C 6 H 14 insoluble in water soluble in gasoline flammable low mp -95 o C low bp 69 o C low density 0.66g/cm 3 covalent bonds Created By C. Ippolito Dec 2006 Sodium Chloride – NaCl soluble in water insoluble in gasoline not flammable high mp 801 o C high bp 1413 o C high density 2.7g/cm 3 ionic bonds

Alkanes long chains of carbon formula C n H 2n+2 -ane ending indicates all C-C single bonds named using prefixes to indicate number of carbon atoms Created By C. Ippolito Dec = meth- 3 = prop- 5 = pent- 7 = hept- 9 = non- 2 = eth- 4 = but- 6 = hex- 8 = oct- 10 = dec-

Naming Branched Alkanes Name made of two parts CBLNA: 1.end of the name is the name of the longest chain (see Table 19.3 on p. 584) 2.first part of name consists of the name of the groups attached to the main chain group names come from prefixes with –yl ending 3.location of group given by number of carbon atom in main chain 4.two or more identical groups are identified using Latin prefixes 5.if more than one group attached name of groups are listed in alphabetical order. Created By C. Ippolito Dec 2006

Properties of Alkanes 1-4 carbons – gases at room temperature 5-16 carbons - liquids at room temperature > 16 carbons – solids at room temperature Reactions all undergo combustion with oxygen (burn) CH 4 (g) + 2O 2 (g)  CO 2 (g) + 2H 2 O(g) + heat combine with halogens to form alkyl halides CH 4 (g) + Br 2 (l)  CH 3 Br(g) + HBr(g) one –H on methane “substituted” by a -Br Created By C. Ippolito Dec 2006

Hydrocarbons organic compounds composed mainly of hydrogen and carbon SATURATED – each carbon atom bonded to FOUR other atoms Alkane – all C to C single bonds UNSATURATED – at least one pair of carbons bonded to less than FOUR atoms Alkene – at least one C to C double bond Alkyne – at least one C to C triple bond Created By C. Ippolito Dec 2006

Naming Branched Alkenes and Alkynes Name made of two parts CLBLNA: 1.end of the name is the name of the longest chain (see Table 19.3 on p. 584) with –ene ending using lowest number carbon to tell where = bond is located 2.first part of name consists of the name of the groups attached to the main chain group names come from prefixes with –yl ending 3.location of group given by number of carbon atom in main chain 4.two or more identical groups are identified using Latin prefixes 5.if more than one group attached name of groups are listed in alphabetical order. Created By C. Ippolito Dec 2006

Isomers Hydrocarbons with same molecular formula different structural formulas butane and isobutane (2-methyl propane) are both C 4 H 10 butane isobutane

Cis-Trans Isomers can only occur in alkenes involves bonds to left and right of double bond cis – when groups are on the same side cis-2-butene trans – when groups are on different sides trans-2-butene

Alkene Reactions Hydrogenation adding hydrogen atoms to unsaturated hydrocarbons to make them saturated trans 2-butene with H 2 added forms butane health issue unsaturated oils/fats vs saturated (hydrogenated) oils/fats

Alkene Reactions (con’t) Halogenation Halogen gases react to form halogenated alkanes trans 2-butene reacts with Cl 2 to form 2,3 dichlorobutane similar reactions can occur with F 2, Br 2, I 2 addition always occurs across the double bond

Aromatic Hydrocarbons Benzene ring of carbon with double bonds formula C 6 H 6 special “double” bonds with resonance all hydrogens are “equal” Created By C. Ippolito Dec 2006

Alcohols -OH a hydroxyl group replaces a hydrogen Methanol or methyl alcohol Ethanol or ethyl alcohol 1,2 ethanediol or ethylene glycol