Updated April 2007Created by C. Ippolito April 2007 Organic Chemistry Objectives 1.State general properties and reactions of organic compounds 2.Compare general formulas and name hydrocarbons 3.Compare saturated and unsaturated compounds 4.State names, formulas, and uses for hydrocarbon derivatives Objectives 1.State general properties and reactions of organic compounds 2.Compare general formulas and name hydrocarbons 3.Compare saturated and unsaturated compounds 4.State names, formulas, and uses for hydrocarbon derivatives

Updated April 2007Created by C. Ippolito April 2007 Hydrocarbons simplest compounds –only carbon and hydrogen aliphatic hydrocarbons –open chains of carbon and hydrogen cyclic hydrocarbons –closed “ring” chains of carbon and hydrogen

Updated April 2007Created by C. Ippolito April 2007 Saturated Hydrocarbons contain only carbon to carbon single bonds contain “maximum” hydrogen

Updated April 2007Created by C. Ippolito April 2007 Unsaturated Hydrocarbons contain at least one carbon to carbon double or triple bonds contain less than “maximum” hydrogen

Updated April 2007Created by C. Ippolito April 2007 Hydrocarbon Series Alkanes –only single bonds, saturated, C n H 2n+2 Alkenes –double bond, unsaturated, C n H 2n Alkynes –triple bond, unsaturated C n H 2n-2 Alkadienes –two separate double bonded carbons

Updated April 2007Created by C. Ippolito April 2007 Homologous Series constant increment of change in molecular structure 1 = meth- 3 = prop- 5 = pent- 7 = hept- 9 = non- 2 = eth- 4 = but- 6 = hex- 8 = oct- 10 = dec-

Updated April 2007Created by C. Ippolito April 2007 Formulas Molecular Formula – C 4 H 10 Structural Formula – Condensed Structural Formulas CH 3 -CH 2 -CH 2 -CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 (CH 2 ) 2 CH 3 Carbon Skeleton – C-C-C-C Line Angle Formula -

Updated April 2007Created by C. Ippolito April 2007 Branched Chains Parent ChainParent Chain –longest continuous carbon chain SubstituentsSubstituents –atoms or atom groups replacing a hydrogen atom alkyl groups –hydrocarbon substituents »CH 3 ― methyl group »CH 3 CH 2 ― ethyl group »CH 3 CH 2 CH 2 ― propyl group

Updated April 2007Created by C. Ippolito April 2007 IUPAC Naming Rules 1.Find longest chain (parent) 2.Number carbons 3.Add numbers to substituent groups 4.Use prefixes for multiple appearances of same group 5.List substituents in alpha order 6.Use punctuation but no spaces

Updated April 2007Created by C. Ippolito April 2007 IUPAC Naming

Updated April 2007Created by C. Ippolito April 2007 Properties of Alkanes 1-4 C – gas 5-16 C - liquid >16 C – solid nonpolar molecules Created By C. Ippolito Dec 2006

Updated April 2007Created by C. Ippolito April 2007 Structural Isomers compounds with the same molecular formula but different structures –different physical and chemical properties

Updated April 2007Created by C. Ippolito April 2007 Stereoisomers atoms joined in same order but positions in space are different –Geometric Isomers orientation around rigid double bond –cis configuration »groups on same side of double bond –trans configuration »groups on different sides of double bond –Optical Isomers four different groups attached to an asymmetric carbon

Updated April 2007Created by C. Ippolito April 2007 Geometric Isomers

Updated April 2007Created by C. Ippolito April 2007 Optical Isomers

Updated April 2007Created by C. Ippolito April 2007 Cyclic Hydrocarbons hydrocarbon chain forms a ring –cyclopropane –cyclobutane –cyclopentane –cyclohexane

Updated April 2007Created by C. Ippolito April 2007 Aromatic Hydrocarbons contains a benzene ring –electrons shared evenly –“resonance” phenyl group –benzene sub

Updated April 2007Created by C. Ippolito April 2007 Substituted Benzene dimethyl benzene – 3 isomers –ortho- 1,2 dimethyl benzene –o-xylene –meta- 1,3 dimethyl benzene –m-xylene –para- 1,4 dimethyl benzene –p-xylene

Updated April 2007Created by C. Ippolito April 2007 Hydrocarbons in Crust Natural Gas –low molar mass 80% methane, 10% ethane, 4% propane, 2% butane Petroleum –fractional distillation separation by boiling points –cracking heat to form smaller chains from larger ones

Updated April 2007Created by C. Ippolito April 2007 Functional Groups specific atomic arrangements that give specific physical and chemical properties hydroxyl carbonyl carboxyl amino amido alcohol aldehyde ketone organic acid amine amide

Updated April 2007Created by C. Ippolito April 2007 Alcohols < 4 water soluble – polar Primary – 1C on C-OH Secondary – 2C on C-OH Tertiary – 3C on C-OH Dihydroxy & Trihydroxy (glycerol)

Updated April 2007Created by C. Ippolito April 2007 Common Alcohols and Uses methanol [1C] ethanol [2C] isopropanol [3C] 1,2 ethandiol glycerol solvent antiseptic antifreeze fat component

Updated April 2007Created by C. Ippolito April 2007 Carboxylic Acids Carboxyl group – carbonyl and hydroxyl group on same carbon –Latin & Greek names for sources methanoic acid [1C] (formic) – ant ethanoic [2C] (acetic) – vinegar propanoic [3C] – butanoic [4C] – –rest are not miscible in water “fatty acids” used to form “fats” with glycerol

Updated April 2007Created by C. Ippolito April 2007 Esters derivative of carboxylic acid and alcohol R 1 -COO-R 2 –pleasant fruity odors –used in fragrances

Updated April 2007Created by C. Ippolito April 2007 Ethers Compound in which oxygen is bonded to two carbon groups General Formula: R-O-R –ethylmethyl ether CH 3 CH 2 -O-CH 3 –diethyl ether CH 3 CH 2 -O-CH 2 CH 3

Updated April 2007Created by C. Ippolito April 2007 Aldehyde / Ketone -C=O –aldehyde – has at least 1 H on –C=O methanal (formaldehyde) – preservative ethanal (acetaldehyde) – “hangover” benzaldehyde – almond odor –ketone – all C on –C=O propanone (acetone) – nail polish remover

Updated April 2007Created by C. Ippolito April 2007 Organic Reactions Substitution –atom/group replaced with another usually H replaced by halogens CH 4 + Cl 2  HCl + CH 3 Cl (chloromethane) Addition –atoms added across double/triple bond hydrogenation – used to solidify liquid vegetable oils hydration – add water across double bond forming an alcohol

Updated April 2007Created by C. Ippolito April 2007 Organic Reactions (con’t) Esterification –dehydration or condensation reaction between an acid and alcohol

Updated April 2007Created by C. Ippolito April 2007 Organic Reactions (con’t) Saponification –hydrolysis of a fat with base (NaOH) to form glycerol and soap (salt of fat)

Updated April 2007Created by C. Ippolito April 2007 Polymerization Polymer –large molecule made of repeating units (monomers) Natural Polymers –proteins (amino acids) –polysaccharides (glucose) –nucleic acids (nucleotides) Synthetic Polymers –plastics (polystyrene, polyvinyl chloride – PVC) –nylons –polyester –teflon (polytetrafluoroethene – PTFE)