SCH 2108: CHEMISTRY IL LECTURE NOTES Dr. Moses A Ollengo. Chemistry Department, Dedan Kimathi University of Technology ORGANIC CHEMISTRY Organic chemistry covers a large class of molecules, all of which contain carbon and hydrogen. Other elements can also be found in molecules that are considered to be organic, such as nitrogen, oxygen, sulfur, and phosphorous. Unique properties of Carbon 1. Carbon is tetravalent i.e it has four valence electrons and therefore can form four strong 8, Brete.). Eg CHs covalent bonds with other carbon atoms or other elements (H2, Pa lige { or { ‘oe sN, ) Vy ‘The arrangement of atoms, which is a tetrahedron with angles of 109,5° between, hydrogens. The arrangement in space about the central carbon can be explained in very simple terms. Each covalent bond contains two electrons and constitutes a region of negative charge. Since four such regions in space must repel one another, they will be as far apart as possible and this puts the hydrogens at the corners of a tetrahedron 2. Catenation is the ability of carbon to form very long chains of interconnecting C-C bonds. Carbon-carbon bonds are strong. and stable and this property allows carbon to form an almost infinite number of compounds; in fact, there are more known carbon-containing compounds than all the compounds of the other chemical elements combined except those of hydrogen (because almost all organic compounds contain hydrogen as well)(CHy-CHh- CH:-CHz-CH:-CH)-CH) 3. Carbon can form multiple bonds including double (alkenes C=C-), or triple bonds with other carbon atoms (alkynes ~C=C-) or other elements e.g Nitrogen. H. aH 1C=C HY” YH H—C=c—H Ethylene Ethyne 4. Carbon ean also form an enormous variety branched compounds and rings of various sizes Zo H; wee. (are cul H. [CH] cHcH,¢ Hydrocarbons Hydrocarbons are compounds composed only of carbon and hydrogen atoms, Hydrocarbons provide the backbone of all organic compounds. Each carbon atom in a hydrocarbon forms a total of four bonds. ‘These bonds are combinations of single bonds with hydrogen atoms and single or multiple bonds with other carbon atoms, Hydrocarbons are classified into alkanes (carbon atoms in the structure are joined by single bonds), alkenes (at least two carbon atoms in the structure are joined by a double bond), and alkynes (at least two carbon atoms in the structure are joined by a triple bond). ‘Organte Compounds occur as: * Straight chains: aliphatic * Branched compounds © Rings Formulas for representation of hydrocarbons 2i. A two-dimensional structural formula of a hydrocarbon shows all of the atoms with all of their bonds in the plane of the page. i. qe tt rl CH amt AL o H ES Hoy\y H un ii. A condensed structural formula includes all of the atoms but uses line bonds to. emphasize the main structural characteristics of the molecule. Eg., for Heptane CHy-CH- CH.-CH.-CH.-CH.-CH, ‘Taking out the lines representing the carbon-carbon bonds condenses this formula to: CHC! 'H>CH.CH>CH2CH;, Since heptane has five repeating —CH— groups, called methylene groups. The formula can be further condensed to: CH,(CH,)sCHy iil. Bond-line formulas represent the carbon atoms as the intersection of lines and as line ends, You assume all the hydrogen atoms needed to complete earbon’s valences. A\/NINWIN nonane NOMENCLATURE OF HYDROCARBONS, Organic compounds are arranged into classes according to the particular functional groups that they contain. ‘Members of each class of compounds share common chemical and physical characteristics. ‘The names of organic compounds are assigned according to the class of the compound as determined by the firnctional groups. TUPAC Guidelines on nomenclature of organic compoundsAlthough called trivial names are known for many organic compounds, they are used colloquially and where itis simplest However, a systematle nomenclature system that chemists use has been adopted by the International Union of Pure and Applied Chemistry (IUPAC) and is internationally accepted as the standard, Under this system one name fits one structure, and each name identifies a structure ‘unambiguously. 1. A systematic name consists of three parts: ‘© A pret: appears before the stem name, and indicates a substituent on the chain (a substituent may be regarded asa group replacing hydrogen in the parent alkane). ‘+ Aste: identifies the longest carbon chain (parent alkane): It is the main part of the name, or it gives an indication of the particular alkane on which the name is based and indicates the number of carbon atoms in the longest carbon chain present in the compound. Forrings the word “cyclo” is added before the stem name © A suffix: identifies the type of compound and appears at the end eg A suffix - ‘ane on the name of an organic compound indicates an alkane. A suffix -ane on the name of an organic compound indicates an alkane, -ene alkenes and -yne for alkynes NB: Before the stem name, a prefix indicates 2 substituent (a substituent may be regarded as a group replocing hydrogen in the parent alkane). Both the nature and position of a substituent must be indicated and are included in the name. No of carbons | Parentstem name ‘Alkane Ring Ic Meth Methane 2c Eth Ethane 3c Prop Propane lopropane aC But Butane cyclobutaneSteps followed when naming organic Compounds 1 3C Pent Pentane eyclopentane oC Hex Hexane ‘cyclohexane 7C Fiept Heptane ‘eycloheptane BC Oct Octane eyelooctane | oC Now Nonane eyclononane ToC Dec Decane ‘eyclodecane he "Undee Undecane uundecane Re Dodee Dodecane eyelododecane Common prefixes for substituents derived from alkanes No of carbons | Prefix/substituent name name | Formula 1c MethyT “CH 2C Ethyl 3C Propyl aC Baty 3C Peniyl oC Hexyl RH R For any alkane, the corresponding group is termed an alkyl substituent. Give the parent name for the structre by counting the number carbons in the longest chain or ring. Eg: longest chain 3c = propane, ring 6C propane -yelohexane2. Number the carbon atoms along the chain to give the lowest number for th the substitutuent. 3. Next name the substituent and indicate its position (by a prefix) The name of the prefix is methy! comes from methane: it is an alkyl substituent. Position of the prefix = 2 unambiguous name is 2-methythexane The compound we have named is different CH,CH,CHCH,CH,CH; E2aRB4 35 6 3-methylhexane 4. For multiple substituents give each substituent a number to indicate its position, and indicate the number substituents by the appropriate prefix: di: two, tr: three, tetra: four ete, CH; CH; | + CH,CHCH;CH,CHCH,CH, hee: SSF Substituents: Methyl No of substituents: 2 Preffix: di 6|. When two or more subts TUPAC name: 2. NB: The name is not 3,6-dimethylheptane because adding the position no on the of substiteuents in2,5-dimethylheptane (2+5= 7) gives a lower number than in 3,6- dimethytheptane (3+6-9) ‘The numbers are separated by a “comma” while a "hyphen" separates numbers from words (i¢., the substituent and the parent alkane), words are linked and not broken with spaces When more than one substituent is present, the alphabetical order is followed; E.g.. Longest chain: 9 carbons; nonane Substituents and positions methyl: 3 and ethyl: 6 Name 6-ethyl-3-methylnonane (e comes before m alphabetically) NB: The lowest numbers are used for any possible choices ‘The multiplier "di" is not considered in the alphabetizing. Hence, the name of the following alkane is S-ethyl-2,3-dimethylheptane: CH, CH,CHCHCH,CHCH,CH, (cm) | (CHC juents are attached on the same carbon, the number indicating the position is repeated in the name. E.g..CH; CCH,CH,CHCH,CF ‘The correct name is 5-ethyl-2,2-dimethylheptane (both the methyl substitutents are attached to carbon number 2) Some trivial nomenclature is retained for simple branched substituents. Eg., cHY is aed the fopropy group H,CH, 4-isopropylheptane CH, CH,CH,CHCHCH,CH,CH; CH(CH3)> 4.1sopropyl-3-methytheptane This compound can be represented as: other common trivially named substituents include:(CH):CHCH- is isobutyl cucHcHCH, secondary-butyl_ (or sec-butyl); sec is an abbreviation for secondary) oe CH — CHy written as (CH3)sC~ is tertiary-butyl or tert-butyl; tert is an abbreviation for tertiary Therefore trivial naming of substituents is as follows: ‘primary (1°): 1 earbon bonded to carbon attached to chain. H I cH oe S& secondary (2°): 2 carbons bonded to carbon attached to chain tertiary (3°): 3 carbons bonded to carbon attached to chain 9. When substituents are halogen atoms, the prefixes fluoro, chloro, iodo, and bromo are used to denote the substituents. Eg.,(CH\CH.CH.CH,Br ; Bromobutane 10, In ring structures the prefix cyclo- indicates presence of a ring of carbon atoms. Such compounds are termed cycloalkanes, CH)—CH, 4 carbon ring: Cyclobutane carbon ring: cyclohexane a e th \ cHj—cH, cyclopropane 2 AN 1 CH; 3 CH 3 cs CH,- CH, +13 methyleyclopentane In these examples, all carbons are identical and they are not numbered. However, sometimes numbering is necessary to define the name unambiguously and to assign the position bearing the substituent as 1. Where more than one substituent is on the ring, the positions of the substituents must be specified in the name, e.g. 10L-ethyl-3-isopropyleyelohexane. NB: The numbering around the ring so as to give the substituents must give the lowest number, Skeletal structures are more commonly used for cyclic compounds ~ the above examples become eo Alternatively, hybrids of the two conventions are often used, ©. CH,CHs ‘CH(CH;)) Example: Name the following compound CH3 | CH3— oe CHsThere are various subdivisions in the classification of hydrocarbons. Alkanes 1s a family of hydrocarbons saturated hydrocarbons in which carbons atoms are linked by single bonds. This means that they are saturated with hydrogen, and that they do not react with hydrogen. They are saturated because the carbon atoms are bonded to maximum no of hydrogen atom. Also called paraffins from the Latin parum affinis, meaning "little affinity implying a lack of reactivity). They are alse referred to as altphaties (from the Greek word aleiphar meaning "fat or oil") Alkanes belong to a homologus series of organic compounds in which the members differ by a constant molecular mass of 14 that is CH2 Abhomologous series is a group of organic compounds having similar structure and similar chemical properties in which the successive compound differs by CH2 group ‘The general formula for alkanes is C,H2q.2. Where n= is an integer 1, 2, When the carbon atoms of a hydrocarbon are linked end to end, we refer to them as being straight chain compounds; a better description is unbranched chain to distinguish branched chain possibilities. ‘The simplest compound is methane. No of carbons | Alkane General Formula] Structural formula Ic Methane CHa CHa 2c Ethane QH6 CHBCHS 3c | Propane Gu —”:té«dMC ac | Butane C4HIO CH3CHICH2CH3 3C Pentane CSHI2 6c Hexane Cons 7C Heptane CTHIG RC Octane C8HIS 9c Nonane COH20 10C | Decane C1OH22 12ul Undecane ISOMERISM Constitutional or structural Isomerlsm: is the existence of compounds such that they have same molecular formula but differ from each other in the arrangement of attachment of the atoms in the structure. Consequently, these are molecules which are fundamentally different from each other, having different amounts of branching in their chains or different positions of functional groups or even possessing entirely different functional groups. Eg., For the formula C,H,» two formulas can be obtained: CHCA ca or 2-methylpropane (n- indicates a normal straight chain arrangement while the ‘iso-' indicates an arrangement containing a (CHs);CH- group). ‘These isomers have differing physical and chemical properties Now consider the next highest member of the alkane family, pentane ‘Thus CH3CH2CH2CH2CHS is pentane or pentane, ea ‘SHI2, Bsopentane These are constitutional isomers of pentane, having the same molecular formula CSH12. Stereolsomerism: the molecules have atoms attached together in the same order, but differ from each other in their spatial (three-dimensional) arrangement ‘You will find that your understanding of this topic will be greatly helped by looking at and building three-dimensional models of the different molecules There are two types of stereoisomerism: ring. © geometric (commonly known as cis- trans) optical isomers Geometric Isomers (cis-trans tsomers) When there is some constraint in a molecule that restricts the free rotation of bonded groups, they become fixed in space relative to each other. Where there are two different groups attached to each of the two carbon atoms that have restricted rotation, this gives rise to two different three-dimensional arrangements of the atoms known as geometric isomers, The restriction on rotation can be caused by a double bond or a cyclic structure as shown below Cis. refers to the is ymer that has the same groups on the same side of the double bond or ‘trans- is the isomer that has the same groups on opposite sides, of across the point of restricted rotation. 4‘These prefixes are given in italics before the name of the compound. Examples H,C. H, H CH. “ Sn C= po H” Nu H.C H cis-but-2-ene . trans-but-2-ene 2. Optical tsomers: are molecules that differ three-dimensionally by the placement of substituents around one or more atoms in a molecule. Optical isomers were given their name because they were first able to be distinguished by how they rotated plane-polarized light. These molecules are not necessarily locked into their positions, but cannot be converted into one another, even by a rotation around a single bond. For example, consider the following two molecules,In the molecule on the left, the chlorine is oriented upward, and in the molecule on the right, the chlorine is oriented downward. (These molecules are presented in Wedge-Dash Notation c LOALKANES In ring structures the prefix cyclo- indicates presence of a ring of carbon atoms are formed when terminal carbon atoms in a straight or branched alkane are joined. ‘These have the general formula CnH2m. Examples are: cyclobutane formed from butane: H; ¢H; —2H CH,—CH; CH,—CH, Cyclohexane formed from hexane: CH, fo ® on ; cH | Hs ‘2H H, CH, CH; Physical properties of alkanes and cycloalkanes: Alkanes are colourless They are water-insoluble 16Their boiling point increases with increase in molecular weight, e.g. CHy n-CaHo n-C7H16 n-C }9H22 bp (O)- 162 o 98 174 1-4: Gaese 5-16C: liquids >I8C: solids Unbranched hydrocarbons have higher boiling points than their branched isomers. ee CH,(CH;)3CH; CH= f-¢ H; CH 36° 3 bp bp 10° 2.2-dimethylpropane For example: n-pentane ‘The unbranched chain alkanes can align themselves more closely, and hence develop stronger intermolecular forces and associations than are possible when branching of the chain is present. ‘The greater the association between the molecules, the higher the boiling point 7Compare the aeatly packed noaane with ite constitutional isomer 2.3,4- Uwimethylhexane: LINN LINN LIVIN LI NININ 4/NVNY—N. LIVI Nonane 2.3.4-Trimethybexane Chemical properties of alkanes and cycloalkanes: As their alternative name ‘paraffin’ implies, alkanes are inert to most common chemical reagents, including: + Strong acids + Strong alkalis + Oxidising agents (under normal laboratory conditions) + Halogens (in the dark) Candle wax and petroleum jelly (Vaseline) are common two high formula weight alkanic compounds Apart from their combustibility they are very stable and unreactive chemicals. 1. Combustion It is an oxidation reaction involving burning of substances in air ‘The combustion (burning) of alkanes produces water (steam) and CO? and heat 18Methane (Natural gas) CH;CH,CH; + 50. —-» 3C0, + 4H,O0 + 2209 kJmol! Propane Similar equations can be written for petrol, which is being oxidised in enormous quantities daly in internal combustion engines. Petrol consists mainly of a complex and variable (depending on its source) mixture of alkanes. While complete combustion of petrol would normally form just carbon dioxide and water, limited oxygen supplies leads to incomplete combustion and the formation of the toxic gas carbon monoxide and carbon (soot), ii, Heating alkanes at high temp in presence of a catalyst results in alkenes. E.g. heat H, y s H CH;—-CH; - 2H ———> C=c catalyst N if H ethene iii, Cracking of alkanes Cracking is the breaking up large hydrocarbon molecules into smaller molecules. This is achieved by using high pressures and temperatures without a catalyst, or lower temperatures and pressures in the presence of a catalyst. ‘The source of the large hydrocarbon molecules is often the naphtha fraction or the gas oil fraction from the fractional di ation of erude oil (petroleum), These fractions are obtained from the distillation process as liquids, but are re-vaporised before cracking, 19‘The hydrocarbon molecules are broken up randomly to produce mixtures of smaller hydrocarbons, some of which have carbon-carbon double bonds. (One possible reaction involving the hydrocarbon Cis: might be CisHy2, ——_p 20244 + Coe + Cotta erere propone cane iv. Reaction with halogens Alkanes react with halogens when heated or in the presence of visible light to form haloalkanes E.g., methane, reacts with chlorine when heated or in the presence of visible light. CH, + Cll —» + HCl chloromethane ‘This reaction (and the oxidation reactions) needs the input of energy either electrical, thermal, or radiant energy. After the first hydrogen atom has been replaced, the reaction can proceed further: hv/Cly hviCh hv, CHC] Se cel, “HCI dichloromethane “HCI “ACT tetrachloromethane (methylene chloride) (carbon tetrachloride) Molecular fluorine, bromine and iodine can undergo the same reaction with light but F2 is explosively reactive and I: barely reacts at all. Chlorine will also react by the same mechanism with other alkanes. For example with ethane 20CH3-CH3 > CH3CH2C1+ HCl chloroethane All the hydrogens in ethane are identical, therefore only one product is formed, but with further reaction the hydrogens are not identical, and the product formed will depend on which hydrogen is replaced, CH,CH,CI Two different sets of hydrogen Therefore two products are obtained, CH3CHCI (1,1 dichloroethane). lichloroethane) and CICH2CH2C1 (1,2- ‘These dichloroethanes are constitutional isomers, For propane, the first halogenation step gives the possibility of two isomeric products: Br hy I CH,CH,CH, + Br, ——> CH;CHCH; + HCBr 1-bromopropane 8% 92% Bromine is said to be regloselecttve in this reaction, preferring to replace the secondary hydrogen much more than a primary hydrogen (a regioselective reaction is a reaction in which one region of the molecule is more reactive than another, thus leading to selective product, formation) In this reaction, two different types of C-H bonds are broken and the relative amounts of product are dependent upon three factors: i. The ease with which the different kinds of hydrogens react with the halogen; ii, The number of each kind of hydrogen in the molecule: the more hydrogens there are of any one type, the greater is the probability of the halogens reacting with them. aiii, The type of halogen. ‘Thus the chlorine atom has greater chance of colliding with a primary hydrogen than a secondary, so that more 1-chloropropane should be produced. Not only is collision between molecules of importance, but collision between certain parts of molecules can also have relevance in the course of a reaction. An organic reaction involves: ‘* breaking of bonds ‘+ Formation of bonds ‘These bonds are covalent; electron pairs are involved It is the sequence in which bond breaking and bond formation occurs as well as how the energy of the system changes during a process which defines the mechanism of a reaction. Uses of alkanes i. Heating ii.electricity generation iii. Cooking iv. production of polymers ¥, serve as intermediates in the synthesis of drugs and pesticides vi. components of gasoline (pentane and octane) vii, paraffin wax Uses of Alkanes According to Number of Carbon Atom 1. ‘The first four alkanes are gases and are used for heating, cooking and electricity generation. © The main components of natural gas are methane and ethane, Propane and Butane are used as LPG (liquefied petroleum gas), ‘© Propane is also used in the propane gas burner, butane in disposable cigarette lighters. ‘© They are also used as propellants in Aerosol sprays. 2. Alkane having carbon number $-8 are volatile liquids. © They are used as fuels 2They are also used as solvents for nonpolar substances. 3. Alkanes from having carbon 9-10 form the major part of Diesel and aviation fuel 4. Alkanes from 17 carbon upwards (solids) form the most important components of Fuel oil and lubricating oil also used as anti-corrosive agents, as their hydrophobic nature ‘means that water cannot reach the metal surface, Many solid alkanes find use as paraffin wax. Alkanes with 35 or more carbon atoms are used for road surfacing 6. Synthetic Polymers such as polyehtylene are alkanes with chains containing hundreds of thousands of carbon atoms. Sources of alkanes: the two msjor sources of alkanes are natural gas and petroleum, Natural gas consists of approximately 90 to 95% methane, 5 to 10% ethane, and a mixture of other relatively low-boiling alkanes (propane, butane and 2-methyipropane), Petroleum is a thi viscous, liquid mixture of thousands of compounds, most of them hydrocarbons, formed by the decomposition of marine plants and animals. The fundamental separation process in refining petroleum is fractional distillation All crude petroleum that enters a refinery goes to distillation units, where it is heated to temperatures as high as 370 to 425°C and separated into fractions, FUNCTIONAL GROUPS Functional group: an atom or group of atoms within a molecule that shows a characteristic set of predictable physical and chemical behaviors. They are they are centers of chemical reactivity Functional groups are important in organic chemistry because: a) They are sites predictable chemical behavior. A particular functional group, in whatever compound itis found, undergo the same types of chemical reactions, b) Determine in large measure the physical properties of a molecule. ¢)_ Serve as the units by which we classify organic compounds into families. 4) Serve as a basis for naming organic compounds. Examples Alkene: defined by the C-C double bond 2a| i Benzene Ring: a special ring of carbons with altemating single and double bonds, has a special degree 0 f stability Alcohol: characterized by the hydroxy, -OH group. It is a very important group in monosaccharides (carbohydrates) Alkyne: defined by the C-C triple bond =c — Alkyl Hallde: haloalkane, replace X in the drawing with a halogen from the periodic table; when drawing a haloalkane be sure to not forget the lone pairs on X. 24N\ c Ether: defined by an oxygen bounded to two carbons. The functional group of ethers can conform to many different functions, making it an important character in synthetic transformations Amine: a carbon molecule bound to a nitrogen. The nitrogen typically has a lone pair of electrons. Ketone: defined by a carbon double bound to an oxygen (different than an aldehyde because it can only be found in the inside of a molecular chain- the carbon does not have to be attached to a hydrogen). Ketones, aldehydes, and carboxylic acids contain the carbonyl functional group: C double bound to O, io: + — Aldehyde: defined by a carbon double bound to an oxygen and single bound to hydrogen; because it is characterized by a bond to hydrogen, it can only be found at the ends of molecular chains 28yylle Actd: characterized by the carboxyl group; RCO2H (R being any subset of a molecule); any molecular chain bound to a carbon, this carbon has a double bond to oxygen and also attached to an alcohol group jo: | Amide: contains the double bond between a carbon and an oxygen, the carbon is also bonded to a nitrogen 26Acid Chlorine: aL. | UNSATURATED HYDROCARBONS Unsaturated Hydrocarbons — contain carbon- carbon double or triple bonds (more . wh (women OF Ame i Aromatics hydrogens can be added). :auaeg). LH H ALKENES. Alkene: an unsaturated hydrocarbon that contains one or more carbon-carbon double bonds. The molecular formula of this group is CnH2n (n is the number of carbon atoms). Alkenes belong to a homologus series of organic compounds in which the members differ by a constant molecular mass of 14 that is CH2 ‘The Suffix = -ene is added to the prefix indicating the longest carbon chain. Alkenes have less hydrogen atoms than alkanes. (C3Hy, CHp=CHs, CHs=CH-CHy In the carbon-carbon double bond, two pairs of electrons are being shared, leaving the carbon free to bond to two other atoms. CHy 'H; ethylene, CoH, CHCHCH) propylene, CoH |UPAC Nomenclature of Atkenes 1. Step 1. Identify and name the longest continuous chain of C atoms which contains the double bonds) (No of C +-ene). 27Step 2. Number the longest chain so that the C’s joined by the double bond have the lowest numbers possible 3. Ifthe double bond has the same position starting from either end, use the positions of the substituents to determine beginning of the chain, 4. Step 3. Locate the double bond by the lower- numbered carbon atom joined by the double bond (e.g., I-butene), Step 4. Locate and name attached groups 6. Step S. Combine the names for the attached groups and the longest chain into the name. im way. H 2_a/ NES ue eK CHCH, Example 1: Provide the IUPAC names for the following compounds CHy—CHy—CH=CH, — CHy—CH==CH—CH; CH3 CHy—CH—CH=CH, = CH>==CH—CH,—CH,—Br CHy—CH, CHsCH,CH,CH2CHCH==CHCHs, I, CHyCHCH,CH3 CHy—CH)—CHy 8. If there is more than one double bond: ~ a counting prefix (di-, tri-, tetra-, ete.) is placed immediately in front of the suffix -ene to indicate the number of double bonds (diene, triene, tetraene, te.) 9. Usually, an “a” is placed before the counting prefix to make pronunciation easier (e.2., butadiene). ~ The starting position of each double bond is indicated by the lower number, separated by commas (e.g., 1,3-butadiene).. 10. For eycloalkenes, the ring is named as cyclo- + no of C + -ene; one of the carbons of the double bond must be numbered “I.” 28Example 2: Provide the IUPAC names for the following compounds CH CHy=CH—CH=CH, caer leooey Hy Cs ‘CH2CHs ou Ib Example 3: Draw structural formulas forthe following molecules: © 2-methyl-2-butene © 4-methyl-t-pentene ‘¢ 2-methyl-3-pentene (what's wrong with this name?) © 4-cthyl-3. Fhexene (what's wrong with this name © 2.3.d-trimethyl-1,3-pentadiene * 1,6-dimethyleyclohexene ‘© S-ethyl-1,3-cyclopentadiene Bonding in Ethylene When two sp"-hybridized carbons are next to each other, two kinds of orbital overlap take place: © end-on-end overlap of the sp’ orbitals to make a o-bond (sigma bond). side-to-side overlap of the unhybridized p orbitals to make a x-bond (pi bond).5. Hedion overtop ‘The Shape of the Ethylene Molecules Since each carbon in the double bond is trigonal planar in shape, the entire ethylene molecule is a flat molecule, with the atoms separated by bond angles of 120° H H Ne < i m, Exercise: 1. Are the following molecules geometric isomers of each other, or are they the same molecule? 4 H CH3 H XY \ c=¢ c=e N / \ CH 4 H H 2. Draw the two geometric isomers of the following molecule: CHCICHCHs 30