: ORGANIC COMPOUNDS ALKANES Urea was first discovered in human urine by H.M. Rouelle in 1773 It was synthesized in 1828 by Friedrich Wöhler and was the first organic compound to be synthesized from inorganic starting materials This discovery prompted Wöhler to write triumphantly to Berzelius:"I must tell you that I can make urea without the use of kidneys, either man or dog. Ammonium cyanate is urea." Friedrich Wöhler, who prepared it from silver isocyanate through a reaction with ammonium chloride AgNCO + NH4Cl → (NH2)2CO + AgCl NH4NCO → (NH2)2CO Although Wöhler was attempting to prepare ammonium cyanate, by forming urea, he inadvertently discredited VITALIZM, the theory that the chemicals of living organisms are fundamentally different from inanimate matter, thus starting the discipline of ORGANIC CHEMISTRY. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES An ORGANIC COMPOUND is any member of a large class of chemical compounds whose molecules contain carbon. The name "ORGANIC" is historical, dating back to the 19th century, when it was believed that organic compounds could only be synthesized in living organisms through VIS VITALIS - the "life-force". ORGANIC CHEMISTRY the study of carbon containing compounds. INORGANIC CHEMISTRY the study of the elements and noncarbon compounds. Inorganic exceptions: CO, CO2, carbonates, bicarbonates, cyanides, cyanates, isocyanates Na2CO3 Chemistry 21A NaHCO3 NaCN NaCNO NaNCO Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Characteristics of organic substances ORGANIC COMPOUNDS are generally covalently bonded. This allows for unique structures such as long carbon chains and rings. Carbon atoms form very stable covalent bonds with one another (catenation). In contrast to inorganic materials, organic compounds typically melt, boil, sublimate, or decompose below 300°C. Neutral organic compounds tend to be less soluble in water compared to many inorganic salts, with the exception of certain compounds such as low molecular weight alcohols and carboxylic acids where hydrogen bonding occurs. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Characteristics of organic substances Organic compounds tend rather to dissolve in organic solvents which are either pure substances like ether or ethyl alcohol, or mixtures, such as the paraffinic solvents such as the various petroleum. Like inorganic salts, organic compounds may also form crystals. Unique property of carbon in organic compounds is that its valency does not always have to be taken up by atoms of other elements, and when it is not, a condition termed unstauration results. In such cases we talk about carbon carbon DOUBLE BONDS or TRIPLE BONDS. Double bonds alternating with single in a chain are called CONJUGATED DOUBLE BONDS. An aromatic structure is a special case in which the conjugated chain is a closed ring. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Carbon compounds Life as we know it is carbon based. This means that most of the compounds you are made of contain the element carbon. You use carbon compounds every day. Plastic, rubber, and gasoline, clothing, markers, tennis rackets, are carbon compounds. Everything in house that is not metal, ceramic or glass is organic/carbon material. In fact, there are over 12 million known pure carbon compounds (and imagine all possible mixtures)! Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES A carbon atom can form chemical bonds with other carbon atoms in long chains Carbon is unique among the elements. or rings. Some carbon compounds contain several thousand carbon atoms. glucose in cells CARBOHYDRATES The carbon compounds in living things are classified into four groups: 1. CARBOHYDRATES 2. LIPIDS fat layer underneath skin - LIPIDS hair - PROTEIN cell membrane - LIPIDS 3. PROTEINS 4. NUCLEIC ACIDS nucleus of cell – nucleic acids (DNA) Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES COMPOUNDS Property Organic Inorganic Bonding covalent ionic or covalent Forces between molecules generally weak quite strong Number of compounds 6 million+ around 250,000 Standard state low melting solid, liquid, or gas solid Water solubilty mostly insoluble mostly soluble Organic solubilty mostly soluble mostly insoluble Color majority colorless often colored Conductibility nonconductors conductors in molten or aqueous state Combustibility often flammable very few burn Rate of reactions slow fast Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES In the ground state of the free carbon atom, there are two unpaired electrons in separate 2p orbitals. In order to form four bonds (tetravalence), need four unpaired electrons in four separate but equivalent orbitals. Chemistry 21A We assume that the single 2s, and the three 2p orbitals of carbon mix into four sp3 hybrid orbitals which are chemically and geometrically identical; the latter condition implies that the four hybrid orbitals extend toward the corners of a tetrahedron centered on the carbon atom. Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Methane is the simplest hydrocarbon; the molecule is approximately spherical, as is shown in the space-filling model: In the ammonia molecule, for example, the nitrogen atom normally has three unpaired p electrons, but by mixing the 2s and 3p orbitals, we can create four sp3-hybrid orbitals just as in carbon. Three of these can form shared-electron bonds with hydrogen, resulting in ammonia, NH3. The fourth of the sp3 hybrid orbitals contains the two remaining outer-shell electrons of nitrogen which form a non-bonding lone pair. In acidic solutions these can coordinate with a hydrogen ion, forming the ammonium ion NH4+. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES OXYGEN Chemistry 21A WATER Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES By replacing one or more of the hydrogen atoms in CH4 with another sp3 hybridized carbon fragments, hydrocarbon chains of any degree of complexity can be built up. The simplest of these is ethane: Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES HYDROCARBONS SATURATED PARAFFINS ALKANES UNSATURATED CYCLOALKANES H H ALKENES H C H C C H H H H RING WITH CONJUGATED DOUBLE BONDS ALKYNES H C C H H C H AROMATICS H H H CONJUGATED DOUBLE BONDS Chemistry 21A ISOLATED DOUBLE BONDS C C C C C C H H H Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES ISOMERS (Greek isos = "equal", méros = "part") are compounds with the same molecular formula but different structural formula A simple example of isomerism is given by propane: it has the formula C3H8O (or C3H7OH) and occurs as two isomers: propan-1-ol (n-propyl alcohol; I) and propan-2-ol (isopropyl alcohol; II) C3H8O propan-1-ol (n-propyl alcohol) propan-2-ol (isopropyl alcohol) ethyl methyl ether Structural isomerism, or constitutional isomerism, is a form of isomerism in which molecules with the same molecular formula have atoms bonded together in different orders Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES position isomerism Example of skeletal isomerism C5H12O C5 H 1 pentan-2-ol 2 n-pentane isopentane (2-methylbutane) functional group isomerism C6H12 pentan-3-ol This type of isomerism is due to the unequal distribution of carbon atoms on either side of functional group. METAMERISM belongs to same homologous series. H3C O C H2 H2 C C4H10O H2 CH3 H C 3 methyl propyl ether 1-hexene C O H2 C CH3 diethyl ether cyclohexane Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES FUNCTIONAL GROUPS are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction(s)regardless of the size of the moleculeit is a part of. However, its relative reactivity can be modified by nearby functional groups. methanol (methyl alcohol) Chemistry 21A Ether (ethyl ether) (diethyl ether) ethane ethene (ethylene) ethyne (acethylene) Cumene (isopropyl benzene) Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES FUNCTIONAL GROUPS are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction(s) regardless of the size of the molecule it is a part of. However, its relative reactivity can be modified by nearby functional groups. methylamine Chemistry 21A acetamide acetaldehyde (ethanal) methyl ethyl ketone (butanone) . C O . carbonyl group acetic acid (ethanoic acid) ethyl butyrate (ethyl butanoate) Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES HYDROCARBONS SATURATED PARAFFINS ALKANES UNSATURATED CYCLOALKANES H H ALKENES H C H C C H H H H RING WITH CONJUGATED DOUBLE BONDS ALKYNES H C C H H C H AROMATICS H H H CONJUGATED DOUBLE BONDS Chemistry 21A ISOLATED DOUBLE BONDS C C C C C C H H H Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Petroleum (L. petroleum, from Greek πετρέλαιον, lit. "rock oil") or crude oil is a naturally occurring, flammable liquid found in rock formations in the Earth consisting of a complex mixture of hydrocarbons of various molecular weights, plus other organic compounds. Four different types of hydrocarbon molecules appear in crude oil. The relative percentage of each varies from oil to oil, determining the properties of each oil Chemistry 21A Composition by weight Hydrocarbon Average Range Alkanes 30% 15 to 60% Cycloalkanes 49% 30 to 60% Aromatics 15% 3 to 30% Asphaltics 6% remainder Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES ALKANES ≡ PARAFFINS Latin parum (= barely) + affinis with the meaning here of "lacking affinity" Name Molecular Formula Structural Formula Isomers Name Molecular Formula Structural Formula Isomers methane CH4 CH4 1 hexane C6H14 CH3(CH2)4CH3 5 ethane C2 H6 CH3CH3 1 heptane C7H16 CH3(CH2)5CH3 9 propane C3 H8 CH3CH2CH3 1 octane C8H18 CH3(CH2)6CH3 18 butane C4H10 CH3CH2CH2CH3 2 nonane C9H20 CH3(CH2)7CH3 35 pentane C5H12 CH3(CH2)3CH3 3 decane C10H22 CH3(CH2)8CH3 75 CH3– C2H5– CH3CH2CH2– (CH3)2CH– Ethyl Propyl Isopropyl Alkyl Group Name Methyl Chemistry 21A CH3CH2CH2CH2– Butyl Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES THE ALPHABET OF ORGANIC CHEMISTRY methane CH4 CH4 1 hexane C6H14 CH3(CH2)4CH3 5 ethane C2 H6 CH3CH3 1 heptane C7H16 CH3(CH2)5CH3 9 propane C3 H8 CH3CH2CH3 1 octane C8H18 CH3(CH2)6CH3 18 butane C4H10 CH3CH2CH2CH3 2 nonane C9H20 CH3(CH2)7CH3 35 pentane C5H12 CH3(CH2)3CH3 3 decane C10H22 CH3(CH2)8CH3 75 Alkyl Group Name CH3– Methyl C2H5– CH3CH2CH2– (CH3)2CH– Ethyl Propyl Isopropyl Chemistry 21A CH3CH2CH2CH2– Butyl Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES General formula for alkanes: Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Nowadays, the main source of methane is "Natural Gas", which originates in the same way as crude oil, by the anaerobic decomposition of microscopic sea animals under the pressure of layers of silt and mud over a period of millions of years. This can also occur in swamps and marshes, when plant matter decays ("marsh gas"), and in landfill sites; in digesters breaking down sewage sludge; and by enteric fermentation in livestock (e.g. ruminants such as cattle and sheep), as well as being formed when termites digest the cellulose in the wood they have eaten. anaerobic in absence of air (oxygen) Cows and other ruminants have methanogenic bacteria in their rumen which can turn digested carbon compounds into methane, emitted as flatus, some 200-300 litres of gas a day. Most of the flatus is nitrogen, but cases have been reported of cows' flatus being ignited, though not explosively. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES The alkanes from pentane (C5H12) to octane (C8H18) are refined from petroleum into gasoline, the ones from nonane (C9H20) to hexadecane (C16H34) into diesel fuel and kerosene (primary component of many types of jet fuel), and the ones from hexadecane upwards into fuel oil and lubricating oil. At the heavier end of the range, paraffin wax is an alkane with approximately 25 carbon atoms, while asphalt has 35 and up. pentane (C5H12) to octane (C8H18) paraffin wax C9H20 to C16H34 approximately 25 carbon atoms Chemistry 21A asphalt has 35 C and up Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES H3C C H2 H2 C CH3 CH3 C H3C H CH3 Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES NORMAL ALKANE = STRAIGHT CHAIN ISOMER BRANCHED ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CONFORMATIONS CONFORMATIONAL ISOMERISM is a form of stereoisomerism in which molecules with the same structural formula (same connectivity) exist as different conformational isomers or conformers in 3-D due to rotations about one or more σ (single) bonds. The most stable conformer staggered ethane eclipsed ethane The most unstable conformer Natta projection method: Solid or dashed wedged bonds represent bonds pointing above-the-plane or below-the-plane of the paper, respectively. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CONFORMATIONS Newman projection formulas H H3C H2 C butane C H2 CH3 H3C H CH3 staggered butane H H The most stable conformer H3C C C H2 H2 CH3 The most unstable conformer eclipsed butane Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES IUPAC Rules for Alkane Nomenclature 1. Find and name the longest continuous carbon chain. 2. Identify and name groups attached to this chain. 3. Number the chain consecutively, starting at the end nearest a substituent group. 4. Designate the location of each substituent group by an appropriate number and name. 5. Assemble the name, listing groups in alphabetical order. The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing. ALKYL GROUP is a group differing by one hydrogen from alkane Group Name CH3– Methyl C2H5– CH3CH2CH2– (CH3)2CH– Ethyl Propyl Isopropyl Chemistry 21A CH3CH2CH2CH2– Butyl Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES non-alkyl groups: Group F Cl Br I NO2 NH2 Name fluoro chloro bromo iodo nitro amino Systematic name Common/Trivial name(s) Chem. formula Chloromethane Methyl chloride CH3Cl Dichloromethane Methylene chloride CH2Cl2 Trichloromethane Chloroform CHCl3 Tetrachloromethane Carbon tetrachloride, Freon 10 CCl4 polytetrafluoroethene PTFE, Teflon -[CF2-CF2]x it is the only known surface to which a gecko cannot stick H3C NO2 nitromethane methylamine Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES General (IUPAC) nomenclature principle CH3CH2CH2CH(CH3)2 CH3CH2C(CH3)2CH2CH2CH3 PREFIX ROOT ENDING number and identity of attached groups longest carbon chain functional class (CH3CH2)2CHCH2CH(CH3)2 Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CH3CH2CH2CH(CH3)2 Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C5 therefore root = pent The branch is a C1 alkyl group i.e. a methyl group The first point of difference rule requires numbering from the right as drawn, the substituent locant is 2- 2-methylpentane CH3CH2C(CH3)2CH2CH2CH3 (CH3CH2)2CHCH2CH(CH3)2 Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CH3CH2CH2CH(CH3)2 CH3CH2C(CH3)2CH2CH2CH3 3,3-dimethylhexane Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C5 therefore root = pent The branch is a C1 alkyl group i.e. a methyl group The first point of difference rule requires numbering from the right as drawn, the substituent locant is 2- 2-methylpentane Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C6 therefore root = hex There are two substitutents, both C1 alkyl group i.e. methyl groups The first point of difference rule requires numbering from the left as drawn, the substituent locants are 3- and 3- (CH3CH2)2CHCH2CH(CH3)2 Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CH3CH2CH2CH(CH3)2 CH3CH2C(CH3)2CH2CH2CH3 3,3-dimethylhexane (CH3CH2)2CHCH2CH(CH3)2 4-ethyl-2-methylhexane Chemistry 21A Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C5 therefore root = pent The branch is a C1 alkyl group i.e. a methyl group The first point of difference rule requires numbering from the right as drawn, the substituent locant is 2- 2-methylpentane Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C6 therefore root = hex There are two substitutents, both C1 alkyl group i.e. methyl groups The first point of difference rule requires numbering from the left as drawn, the substituent locants are 3- and 3- Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C6 therefore root = hex One C1 alkyl group substituent i.e. a methyl group One C2 alkyl group substituent i.e. an ethyl group The first point of difference rule requires numbering from the right as drawn, the substituent locants are 2- and 4- Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES The longest chain: PENTANE Substrituents: three methyl groups Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES The longest chain: PENTANE Substrituents: three methyl groups Name: 2,2,4-trimethylpentane Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Examples of Simple Cycloalkanes Name Molecular Formula Cyclopropane C3H6 Cyclobutane Cyclopentane C4H8 C5H10 Structural Formula Cyclohexane C6H12 Cycloheptane C7H14 Cycloalkane CnH2n (CH2)n Line Formula Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CYCLOHEXANE Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Alicyclic compounds can display cis-trans isomerism (geometric isomerism or configuration isomerism) When the substituent groups are oriented in the same direction, the diastereomer is When the substituents are oriented in opposing directions, the diastereomer is referred to as cis referred to as trans. cis-1,2-dichlorocyclohexane Chemistry 21A trans-1,2-dichlorocyclohexane Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES 1,1-dimethylcyclohexane 1-t-butyl-1-methylcyclohexane cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES cis-1,2-dimethylcyclopentane trans-1,2-dimethylcyclopentane cis-1,2-dibromocyclopentane trans-1,2-dibromocyclopentane Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Melting (blue) and boiling (pink) points of the first 14 n-alkanes in °C. CH4 to C4H10 alkanes are gaseous; from C5H12 to C17H36 they are liquids; and after C18H38 they are solids R.T. As a rule of thumb, the boiling point rises 20 - 30 °C for each carbon added to the chain A straight-chain alkane will have a boiling point higher than a branched-chain alkane due to the greater surface area in contact, thus the greater van der Waals (dispersion) forces, between adjacent molecules. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES a HOMOLOGOUS SERIES is a series of organic compounds with a similar general formula, possessing similar chemical properties due to the presence of the same functional group, and shows a gradation in physical properties as a result of increase in molecular size and mass HYDROPHOBIC (water in Greek hydro- and fear phobos) refers to the physical property of a molecule (known as a hydrophobe) that is repelled (insoluble in) from a mass of water. HYDROPHILIC, from the Greek (hydros) "water" and φιλια (philia) "friendship," refers to a physical property of a molecule that can transiently bond with water (H2O) through hydrogen bonding Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CH4 + 2O2 → CO2 + 2H2O + 213 kcal/mol Provided the combustion is complete, all the hydrocarbons will burn with a blue flame. However, combustion tends to be less complete as the number of carbon atoms in the molecules rises. That means that the bigger the hydrocarbon, the more likely you are to get a yellow, smoky flame. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Incomplete combustion (where there isn't enough oxygen present) can lead to the formation of carbon or carbon monoxide. As a simple way of thinking about it, the hydrogen in the hydrocarbon gets the first chance at the oxygen, and the carbon gets whatever is left over! 2CH4 + 3O2 → 2CO + 4H2O CH4 + O2 → C + 2H2O The presence of glowing carbon particles in a flame turns it yellow, and black carbon is often visible in the smoke. Carbon monoxide is produced as a colourless poisonous gas. Oxygen is carried around the blood by haemoglobin (US: hemoglobin). Unfortunately carbon monoxide binds to exactly the same site on the haemoglobin that oxygen does. The difference is that carbon monoxide binds irreversibly - making that particular molecule of haemoglobin useless for carrying oxygen. If you breath in enough carbon monoxide you will die from a sort of internal suffocation. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CRACKING is the process whereby complex organic molecules such as kerogens or heavy hydrocarbons are broken down into simpler molecules (e.g. light hydrocarbons) by the breaking of carbon-carbon bonds in the precursors. CRACKING, also referred to as PYROLYSIS, is the breakdown of a large alkane into smaller, more useful alkanes and an alkene. Simply put, hydrocarbons cracking is the process of breaking long chain hydrocarbons into short ones. Factory of Shukhov cracking process, Baku, USSR, 1934. Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES CH4 + Cl2 + energy CH4 + Cl2 + energy ——> ——> CH3Cl + HCl CH3Cl + CH2Cl2 + CHCl3 + CCl4 + HCl The relative amounts of the various products depend on the proportion of the two reactants used. In the case of methane, a large excess of the hydrocarbon favors formation of methyl chloride as the chief product; whereas, an excess of chlorine favors formation of chloroform and carbon tetrachloride. Alkanes react easily with halogens forming haloalkanes. Chemistry 21A Systematic name Common/Trivial name(s) Chem. formula Chloromethane Methyl chloride CH3Cl Dichloromethane Methylene chloride CH2Cl2 Trichloromethane Chloroform CHCl3 Tetrachloromethane Carbon tetrachloride, Freon 10 CCl4 polytetrafluoroethene PTFE, Teflon -[CF2-CF2]x Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic : ORGANIC COMPOUNDS ALKANES Chemistry 21A Dr. Dragan Marinkovic