CHEMICAL BONDING Cocaine Water 2 Chapter 9 Outline • • • • Ionic -vs- Covalent Bonding in molecules Valance electrons Lewis Structures – Oxidation Numbers – Formal Charges • VESPR Chemical Bonding Problems and questions — How is a molecule or polyatomic ion held together? Why are atoms distributed at strange angles? Why are molecules not flat? Can we predict the structure? How is structure related to chemical and physical properties. Forms of Chemical Bonds • There are 2 extreme forms of connecting or bonding atoms: • Ionic—complete transfer of electrons from one atom to another • Covalent—electrons shared between atoms • Most bonds are somewhere in between. Complete electron Ionic transfer from an element of low IE (metal) to an element of high EA (nonmetal) Bonds 2 Na(s) + Cl2(g) ---> 2 Na+ + 2 Clresults in a metal/nonmetal or ionic compound. Covalent Bonding Covalent bond forms by the sharing of VALENCE ELECTRONS, between two nonmetals. Valence Electrons Electrons are divided between core and valence electrons. Na 1s2 2s2 2p6 3s1 Core = [Ne] and valence = 3s1 Br [Ar] 3d10 4s2 4p5 Core = [Ar] 3d10 and valence = 4s2 4p5 . 35 : Br: [Ar] 3d10 4s24p5 8 Valence Electrons Covalent Bonding The bond arises from the mutual attraction of 2 nuclei for the same electrons. A Bond is a balance of attractive and repulsive forces. Chemical Bonding Objectives Objectives are to understand: 1. e - distribution in molecules and ions. 2. molecular structures. 3. bond properties and their effect on molecular properties. Electron Distribution in Molecules • Electron distribution is depicted with Lewis electron dot structures • Electrons are distributed as shared or BOND PAIRS and unshared or LONE PAIRS. G. N. Lewis 1875 - 1946 Bond and Lone Pairs Electrons are distributed as shared or BOND PAIRS and unshared or LONE PAIRS. •• H Cl • • •• shared or bond pair lone pair (LP) This is called a LEWIS ELECTRON DOT structure. 13 Lewis Dot Electron Configs Bond Formation A bond can result from a “head-to-head” overlap of atomic orbitals on neighboring atoms. •• H + Cl •• •• • • H Cl • • •• Overlap of H (1s) and Cl (3p) This type of overlap places bonding electrons in a MOLECULAR ORBITAL along the line between the two atoms and forms a SIGMA BOND (). Rules of the Game Observation that atoms want to obtain a filled noble gas electron configuration is called the OCTET RULE • There are exceptions to these rules!!! Building a Dot Structure Ammonia, NH3 1. Decide on the central atom; never H. Central atom is atom of lowest affinity for electrons. Therefore, N is the central atom. 2. Count valence electrons H = 1 and N = 5 Total = (3 x 1) + 5 = 8 electrons / 4 pairs Building a Dot Structure 3. Form a sigma bond between the central atom and surrounding atoms. H N H H 4. Remaining electrons go to the central atom to form LONE •• PAIRS to complete octet as H N needed. 3 BOND PAIRS and 1 LONE H PAIR. Note that N has a share in 4 pairs (8 electrons), while H shares 1 pair. H Sulfite ion, SO32Step 1. Central atom = S Step 2. Count valence electrons S= 6 3 x O = 3 x 6 = 18 Negative charge = 2 TOTAL = 26 e- or 13 pairs Step 3. Form sigma bonds Sulfite ion, SO32Step 1. Central atom = S Step 2. Count valence electrons S= 6 3 x O = 3 x 6 = 18 Negative charge = 2 TOTAL = 26 e- or 13 pairs Step 3. Form sigma bonds O 10 pairs of electrons are now left. O S O Sulfite ion, SO32Remaining pairs become lone pairs, first on outside atoms and then remaining pairs on central atom. • • • • O •• O •• -2 •• • • •• S •• O •• •• Each atom is surrounded by an octet of electrons. Carbon Dioxide, CO2 C 1. Central atom = _______ 2. Valence electrons = __ 16 or __ 8 pairs 3. Form sigma bonds. O C O This leaves 6 pairs. 4. Place lone pairs on outer atoms. •• •• • • O •• C O •• • • Carbon Dioxide, CO2 4. Place lone pairs on outer atoms. •• •• • • O C •• O • • •• 5. So that C has an octet, we form DOUBLE BONDS between C and O. •• •• • • O •• C O •• • • • • O •• C The second bonding pair forms a pi bond. O •• (p) • • Double and even triple bonds are commonly observed for C, N, P, O, and S C2F4 H2CO SO3 Sulfur Dioxide, SO2 1. Central atom = S 2. Valence electrons = 18 or 9 pairs •• • • O •• •• •• S O • • •• 3. Form pi (p) bond so that S has an octet — but note that there are two ways of doing this. OR bring in right pair bring in left pair •• • • O •• •• S •• O •• • • Sulfur Dioxide, SO2 OR bring in right pair bring in left pair •• • • •• •• O S •• O • • •• This leads to the following structures. • • O •• •• S •• O •• • • • • •• •• O S •• O •• •• These equivalent structures are called RESONANCE STRUCTURES. The true electronic structure is a HYBRID of the two. Urea, (NH2)2CO 1. Arrangement, is C or O the central atom? 2. Number of valence electrons = 24 e- 3. Draw sigma bonds. O C O H N H C N H H Urea, (NH2)2CO 4. Place remaining electron pairs in the molecule. •• •• O •• H N H • • •• C N H H 5. Carbon needs an Octet, take from the Oxygen Urea, (NH2)2CO Exceptions to the Octet Rule Occurs with B (the only 2nd period exception) and elements of 3rd - 7th periods. BF3 SF4 Boron Trifluoride • • • • Central atom = Valence electrons = or electron pairs = Assemble dot structure •• • • F • • •• • • F B •• • • F •• • • The B atom has a share in only 6 electrons (or 3 pairs). The B atom in many molecules is electron deficient. Sulfur Tetrafluoride, SF4 • Central atom = • Valence electrons = ___ or ___ pairs. • Form sigma bonds and distribute electron pairs. •• • • •• F •• •• • • F •• S •• F •• •• F •• • • • • 5 pairs around the S atom. A common occurrence outside the 2nd period. Draw Lewis Structures for: N2 CH4 I2CO HCOOH NO2- XeF4 Oxidation Number • Oxidation Number is assigned based on a set of rules. • These rules are based on the Lewis Structures of the compounds or ions. • Oxidation Number = Group no. - (no. assigned electrons) - (no. of LP electrons) Sample Problem Formal Atom Charges • Atoms in molecules often bear a charge (+ or -). • The predominant resonance structure of a molecule is the one with charges as close to 0 as possible. • Formal charge = Group no. - 1/2 (no. bond electrons) - (no. of LP electrons) Carbon Dioxide, CO2 Formal charge calculations 6 - (1/ 2)(4) - 4 •• • • O •• C 4 - (1/ 2)(8) - 0 O = • • 0 = 0 Carbon Dioxide, CO2 6 - (1/ 2)(2) - 6 •• • • O C 6 - (1/ 2)(6) - 2 O • • •• = -1 C atom charge is 0. = +1 Which is the predominant resonance structure? Carbon Dioxide, CO2 -0.73 -0.73 +1.46 Actual partial charges. Boron Trifluoride, BF3 •• • • • • F •• • • F •• B • • • • F •• What if we form a B—F double bond to satisfy the B atom octet? Boron Trifluoride, BF3 •• • • F fc = 7 - 2 - 4 = +1 •• • • F •• B fc = 3 - 4 - 0 = -1 • • • • F •• • To have +1 charge on F, with its very high affinity for electrons, is not good. • Negative charges are best placed on atoms with high affinity for electrons. Thiocyanate ion, SCNWhich of three possible resonance structures is the most important? Calculate the formal charge for each element. Thiocyanate ion, -0.16 -0.52 SCN -0.32 Calculated partial charges PRACTICE PROBLEM Ox # = group # - lone pair electrons assigned electrons F.C. = group # - lone pair electrons - 1/2 bonding electrons Practice Problem Determine oxidation numbers and formal charges for the atoms in SO3-2. MOLECULAR GEOMETRY MOLECULAR GEOMETRY VSEPR • Valence Shell Electron Pair Repulsion theory. • Most important factor in determining geometry is relative repulsion between electron pairs. Molecule adopts the shape that minimizes the electron pair repulsions. Figure 9.11 Figure 9.12 No. of e- Pairs Around Central Atom 2 Example F—Be—F Geometry linear 180 F 3 F planar trigonal B F 120 H 4 C H 109 tetrahedral H H Notice where the central atom is 4 electron pair groups Electron pair geometry 48 Molecular Shape name Electron pair geometry Figure 9.14 Molecular name Brief Summary of VESPR 50 Electron Pair Geometry Molecular Geometry 2 electron pairs Linear Linear 3 electron pairs Trigonal Planar Trigonal Planar Trigonal Planar “V” Bent 4 electron pairs Tetrahedral Tetrahedral Tetrahedral Trigonal Bipyramidal Tetrahedral Trigonal Pyramidal “V” Bent “look all 4 of them up” Octahedral “look all 4 of them up” 5 electron pairs 6 electron pairs 14 possible combinations….learn them all! Structure Determination by VSEPR Ammonia, NH3 1. Draw electron dot structure •• H N H H 2. Count BP’s and LP’s around central N atom = 4 (Called the number of structural pairs.) Structure Determination by VSEPR Ammonia, NH3 H 1. Draw electron dot structure 2. Count BP’s and LP’s = 4 3. The 4 electron pairs are at the corners of a tetrahedron. H H N H H lone pair of electrons in tetrahedral position N H •• Structure Determination by VSEPR Ammonia, NH3 There are 4 electron pairs at the corners of a tetrahedron. lone pair of electrons in tetrahedral position •• H N H H N H H H The ELECTRON PAIR GEOMETRY is tetrahedral. Structure Determination by VSEPR Ammonia, NH3 The electron pair geometry is tetrahedral. lone pair of electrons in tetrahedral position N H H H The MOLECULAR GEOMETRY or SHAPE — the positions of the atoms — is Trigonal PYRAMIDAL. 55 VESPR Step-by-step Determination 1 2 Structure Determination by VSEPR Water, H2O 1. Draw electron dot structure •• H O•• H 2. Count BP’s and LP’s = 4 Structure Determination by VSEPR Water, H2O 1. Draw electron dot structure 2. Count BP’s and LP’s = 4 3. The 4 electron pairs are at the corners of a tetrahedron. O H H The electron pair geometry is TETRAHEDRAL. •• H O•• H Structure Determination by VSEPR Water, H2O •• H O•• H O H H The molecular geometry is bent 109.5 The electron pair geometry is TETRAHEDRAL. Structure Determination by VSEPR Formaldehyde, CH2O 1. Draw electron dot structure • • H O •• C H Structure Determination by VSEPR Formaldehyde, CH2O • • 1. Draw electron dot structure 2. Count BP’s and LP’s = 3 H (the double bond is treated as a “lump” of electrons or one pair) O •• C H Structure Determination by VSEPR Formaldehyde, CH2O • • O •• 1. Draw electron dot structure H C 2. Count BP’s and LP’s = 3 3. There are 3 electron pairs are at the corners of a planar triangle. • • O •• C H H H The electron pair geometry is TRIGONAL PLANAR with 120o bond angles. Structure Determination by VSEPR Formaldehyde, CH2O • • O •• The electron pair geometry is TRIGONAL PLANAR C H H The molecular geometry is also TRIGONAL PLANAR. Structure Determination by VSEPR Methanol, CH3OH 1. Draw electron dot structure H •• H—C—O—H •• 1 H 2 2. Define bond angles 1 and 2 Structure Determination by VSEPR Methanol, CH3OH 1 H H C O H 2 Define bond angles 1 and 2 In both cases the atom is surrounded by 4 electron pairs. H Structure Determination by VSEPR Acetonitrile, CH3CN Define bond angles 1 and 2 Angle 1 = 109o Angle 2 = 180o One C is surrounded by 4 electron “lumps” and the other by 2 “lumps” Determine the bond angles. : Phenylalanine, an amino acid 120o 109o 109o 109o 120o Compounds with 5 or 6 Pairs Around the Central Atom Compounds with 5 or 6 Pairs Around the Central Atom 90 F F P Trigonal bipyramid F 120 5 electron pairs F F 90 6 electron pairs F F S F F Octahedral F F 90 69 STRUCTURES WITH CENTRAL ATOMS THAT DO NOT OBEY THE OCTET RULE 70 Deviations from the Octet Rule Usually occurs with Group 3A elements and with those of 3rd period and higher. Consider boron trifluoride, BF3 •• F • • • • •• • • F •• B • • • • F •• 71 Deviations from the Octet Rule Consider boron trifluoride, BF3 •• The B atom is surrounded by only 3 electron pairs. Bond angles are 120o Geometry described as planar trigonal • • • • F •• • • F •• B • • • • F •• Sulfur Tetrafluoride, SF4 • Number of valence electrons = • Central atom = • Dot structure Sulfur Tetrafluoride, SF4 • Number of valence electrons = 34 • Central atom = S • Dot structure •• •• •• F •• •• •• ••F S F•• •• •• •• F•• •• Sulfur Tetrafluoride, SF4 Number of valence electrons = 34 •• Central atom = S •• •• F •• •• Dot structure •• • • F ••• S F• •• •• F•• •• Electron pair geometry = ? Sulfur Tetrafluoride, SF4 • Number of valence electrons = 34 • Central atom = S • Dot structure •• •• •• F •• ••• •• ••F S F• •• •• •• F•• •• Electron pair geometry = trigonal bipyramid (because there are 5 pairs around the S) What is the Molecular Geometry? Sulfur Tetrafluoride, SF4 Not all repulsions are equivalent. L.P. - L.P. > L.P. - B.P. > B.P. - B.P. Minimize lone pair bond pair repulsions at the 90o angle. 90 •• F S F F F 120 Structural Determination Determine the geometries for PF3, NO2-, NO2+, ICl2-, ClF3, ClF5, and IBr4-, giving VSEPR class, shape name, 3-D diagram, and bond angles. Solutions Bond Properties • What is the effect of bonding and structure on molecular properties? Buckyball in HIV-protease Bond Order • The number of bonds between a pair of atoms. H single BO = 1 1 H H C C triple, BO = 3 1 and 2 p C N double, BO = 2 1 and 1 p Bond Order Fractional bond orders occur in molecules with resonance structures. Consider NO2•• •• •• O •• N •• • O• •• •••• O •• N •• O •• The N—O bond order = 1.5 Total # of e - pairs used for a type of bond Bond order = Total # of bonds of that type 3 e - pairs in N — O bonds Bond order = 2 N — O bonds Bond Order Bond order is proportional to two important bond properties: (a) bond strength (b) bond length 110 pm 745 kJ 414 kJ 123 pm Bond Length Bond length is the distance between the nuclei of two bonded atoms. Bond Length Bond length depends on size of bonded atoms. H—F H—Cl Bond distances measured in Angstroms or pm where 1 A = 100 pm. H—I Bond Length Bond length depends on bond order. Different C-O Bond Lengths C-C bond lengths C-N bond lengths Bond Strength • Bond strength is measured by the energy required to break a bond. See Table 9.9 C-C bond strengths Bond Strength BOND H—H C—C C=C CC NN STRENGTH (kJ/mol) 436 346 602 835 945 The GREATER the number of bonds (bond order) the HIGHER the bond strength and the SHORTER the bond. Bond Strengths for O-O Bond HO—OH •• O •• •• O O=O Order Length 1 147 pm 210 kJ/mol 128 394 ? 121 498 •• • 1.5 O• •• 2 Strength Using Bond Energies DHorxn = S H (bonds broken) S H (bonds formed) or DHorxn = energy input (+) + energy output (-). Net energy = DHrxn, bond = energy required to break bond energy evolved when bonds are formed. Using Bond Energies Estimate the energy of the reaction H—H + Cl—Cl ----> 2 H—Cl H—H = 436 kJ/mol Cl—Cl = 242 kJ/mol H—Cl = 432 kJ/mol Sum of H-H + Cl-Cl bond energies = 436 kJ + 242 kJ = +678 kJ 2 mol H-Cl bond energies = 864 kJ Net = DH = +678 kJ - 864 kJ = -186 kJ Using Bond Energies Estimate the energy of the reaction 2 H—O—O—H ----> O=O + 2 H—O—H Is the reaction exo- or endothermic? Which is larger: energy req’d to break bonds or energy evolved on making bonds? Using Bond Energies 2 H—O—O—H ----> O=O + 2 H—O—H Energy required to break bonds: break 4 mol of O—H bonds = 4 (463 kJ) break 2 mol O—O bonds = 2 (146 kJ) TOTAL ENERGY to break bonds = 2144 kJ Using Bond Energies 2 H—O—O—H ----> O=O + 2 H—O—H Energy evolved on making bonds: make 1 mol of O=O bonds = 498 kJ make 4 mol O—H bonds = 4 (463 kJ) TOTAL ENERGY evolved on making bonds = 2350 kJ Using Bond Energies 2 H—O—O—H ----> O=O + 2 H—O—H Net energy = +2144 kJ - 2350 kJ = - 206 kJ The reaction is exothermic! More energy is evolved on making bonds than is expended in breaking bonds. Calculate DHorxn for the reaction below using bond energies. CH4 (g) + 2 O2 (g) ______> 2 H2O (g) + CO2 (g) DH = [4(C-H) + 2(O=O)] - [4(H-O) + 2(C=O)] DH = [4(413kJ) + 2(498kJ)] - [4(463kJ) + 2(732kJ)] DH = -1166 kJ More Sample Problems! Molecular Polarity Why are water molecules attracted to a balloon that has a static electric charge? Bond Polarity + H - •• Cl •• •• HCl is POLAR because it has a positive end and a negative end. Polarity arises because Cl has a greater share in bonding electrons than does H. Bond Polarity This model, calc’d using CAChe software, shows that H is + (red) and Cl is - (yellow). Calc’d charge is + or - 0.20. This model shows that the electron density is greater around Cl than around H. + H - •• Cl •• •• Bond Polarity Due to the bond polarity, the H—Cl bond energy is GREATER than expected for a “pure” covalent bond. BOND “pure” bond real bond ENERGY 339 kJ/mol calc’d 432 kJ/mol measured Difference = 92 kJ. This difference is proportional to the difference in ELECTRONEGATIVITY, Don’t confuse with mole fraction from Ch 12 . + H - •• Cl •• •• Bond Polarity Partial charge on atom A = Group Number of A - # lone pair electrons - A/(A+ B)( # bonding e- shared by A ) Electronegativity, is a measure of the ability of an atom in a molecule to attract electrons to itself. Concept proposed by Linus Pauling 1901-1994 Linus Pauling, 1901-1994 The only person to receive two unshared Nobel prizes (for Peace and Chemistry). Chemistry areas: bonding, electronegativity, protein structure Electronegativity, See Figure 9.10 • F has maximum . • Atom with lowest is the center atom in most molecules. • Relative values of determine BOND POLARITY (and point of attack on a molecule). Electronegativity, Figure 9.9 Basic Trend = Bond Polarity Which bond is more polar (or DIPOLAR)? O—H O—F 3.5 - 2.1 3.5 - 4.0 D 1.4 0.5 OH is more polar than OF O—H - + O—F + - and polarity is “reversed.” Bond Polarity Relative polarity in a bond is determined by D , where the approximate % ionic character is give by: D = 1.0, 20%; D = 1.5, 40%; D = 2.0, 60%; D = 2.5, 80%. Molecular Polarity Molecules—such as HCl and H2O— can be POLAR (or dipolar). They have a DIPOLE MOMENT. The polar HCl molecule will turn to align with an electric field. Molecular Polarity The magnitude of the dipole is given in Debye units. Named for Peter Debye (1884 - 1966). Received the 1936 Nobel prize for work on x-ray diffraction and dipole moments. Molecular Polarity Molecules will be polar if 1. bonds are polar AND 2. the molecule is NOT “symmetric” Symmetric molecules Molecular Polarity Unsymmetrical Carbon Dioxide • CO2 is NOT polar even though the CO bonds are polar. • CO2 is symmetrical. Positive C atom is reason CO2 + H2O gives H2CO3 Microwave oven Consequences of H2O Polarity Molecular Polarity More Examples F B atom is positive and F atoms are negative. B F F B—F bonds in BF3 are polar. But molecule is symmetrical and NOT polar Molecular Polarity H B atom is positive but H & F atoms are negative. B F F B—F and B—H bonds in HBF2 are polar. But molecule is NOT symmetrical and is polar Polarity of Methane, CH4 H C H H H Methane is symmetrical and is NOT polar. Polarity of CH3F F C H H H C—F bond is very polar. Molecule is not symmetrical and so is polar. Substituted Ethylene • C—F bonds are MUCH more polar than C—H bonds. • Because both C—F bonds are on same side of molecule, molecule is POLAR. Substituted Ethylene • C—F bonds are MUCH more polar than C—H bonds. • Because both C—F bonds are on opposing ends of molecule, molecule is NOT POLAR. Practice Problems 1. Give the VSEPR class, bond angle, shape, and polarity of KrF2, CO, and NO2-. 2. Calculate the heat of reaction for C2H4 (g) + 3 O2 (g) --> 2 CO2 (g) + 2 H2O (g) 3. Calculate the carbon-carbon triple bond energy in C2H2(g). Heat of formation of C2H2 = 226 kJ/mole) 4. Determine the number of p and bonds in acetic acid. 5. Arrange in order of increasing polarity: Sr-Br, P-F, S-F, Al-O Practice Problems Answers 1. AX2E3, 1800, linear, nonpolar AXE, 1800, linear, polar AX2E, 1200, bent, polar 2. -1032 kJ 3. 818 kJ 4. 7 and 1 p 5. S-F, P-F, Al-O, Sr-Br, Ionic Bonding Ionic bonds form by the transferring of VALENCE ELECTRONS, the electrons at the outer edge of the atom. Ionic Bonding Na and F Na 1s22s22p63s1 F 1s22s22p5 Na1+ 1s22s22p6 F1- 1s22s22p6 NaF Ionic Bonding Mg and O Mg 1s22s22p63s2 O 1s22s22p4 Mg2+ 1s22s22p6 O2- 1s22s22p6 MgO Ionic Bonding Mg and F Mg 1s22s22p63s2 F 1s22s22p5 F 1s22s22p5 Mg2+ 1s22s22p6 MgF2 F1- 1s22s22p6 F1- 1s22s22p6 Ionic Bonding Na and O Na 1s22s22p63s1 O 1s22s22p4 Na 1s22s22p63s1 Na1+ 1s22s22p63s1 Na1+ 1s22s22p63s1 O2- 1s22s22p6 Na2O Covalent Bonding Cl and F Cl .F . . Cl . F Covalent Bonding S and F .F .S. F .. S .. F Covalent Bonding O and O O O . . O .. O Sample Problems Draw dot structures for the following: H2O CO NO21-1 H -O- H O N -O -1 C O O- N O Draw Lewis Structures for: N2 CH4 I2CO HCOOH NO2- XeF4 N N Draw Lewis Structures for: H N2 CH4 I2CO HCOOH NO2- XeF4 H C H H Draw Lewis Structures for: N2 CH4 O I2CO HCOOH NO2- XeF4 I C I Draw Lewis Structures for: N2 CH4 I2CO HCOOH NO2- XeF4 O H C O H Draw Lewis Structures for: N2 - CH4 I2CO O N O HCOOH NO2- XeF4 - O O N O Draw Lewis Structures for: N2 CH4 I2CO HCOOH - NO2 XeF4 .. Xe .. Sample Problems Determine the oxidation number for each atom in the following: CO2 SO32O = -2 O = -2 C=4 S=4 Sample Problems Determine the formal charge for each atom in the following: CO NO21O=1 single bond O = -1 C = -1 double bond O = 0 N=0 Structural Determination PF3 PF3 AX3E trigonal pyramidal .. Structural Determination NO2+ NO2+ linear AX2 Structural Determination - ICl2 ICl2- AX2E3 linear 180o 120o .. Structural Determination ClF3 ClF3 AX3E2 T - shaped 120o Structural Determination ClF5 ClF5 AX5E square pyramidal .. Structural Determination - IBr4 IBr4- AX4E2 square planar .. .. Calculate DHorxn for the reaction below using bond energies. C (g) + 2 Cl2 (g) ______> CCl4 (g) DH = [2(Cl-Cl)] - [4(C-Cl)] DH = [2(242 kJ)] - [4(339 kJ)] DH = - 872 kJ Calculate DHorxn for the reaction below using bond energies. C (s) + 2 Cl2 (g) ______> CCl4 (g) DH = [ DHsubC + 2(Cl-Cl)] - [4(C-Cl)] DH = [ 717 kJ + 2(242 kJ)] - [4(339 kJ)] DH = -155 kJ Calculate DHof for CH4 using bond energies. C (s) + 2 H2 (g) --> CH4 (g) DHf = [DHsub C + 2(H-H)] - [4(C-H)] DHf = [ 717 kJ + 2(436 kJ)] - [4(413kJ)] DHf = - 63 kJ Given DHof for C2H4 (g) is 52 kJ/mole. Using bond energies, calculate the carbon carbon bond energy in C2H4 (g). 2 C (s) + 2 H2 (g) -- > C2H4 (g) DHf = [ 2(DHsubC) + 2(H-H) ] - [ 4(C-H) + 1(C=C) ] 52kJ = [ 2(717kJ) + 2(436kJ)] - [4(413kJ) + 1(C=C)] (C=C) = 602 kJ Bond Polarity Ionic Polar Nonpolar Covalent Covalent <--------------------------------------------------------------> :F Li C : F F : F