8.2 The Nature Of Covalent Bonding
8.2 The Nature of Covalent Bonding Chapter 8Covalent Bonding8.1 Molecular Compounds8.2 The Nature of CovalentBonding8.3 Bonding Theories8.4 Polar Bonds and Molecules1Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding CHEMISTRY& YOUWhat is the difference between the oxygenyou breathe and the oxygen in ozone in theatmosphere?Our atmosphere containstwo different moleculesthat are both made ofoxygen atoms.2Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingThe Octet Rule in Covalent BondingWhat is the result of electron sharing incovalent bonds?3Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingIn covalent bonds, electron sharingusually occurs so that atoms attain theelectron configurations of noble gases.4Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingIn covalent bonds, electron sharingusually occurs so that atoms attain theelectron configurations of noble gases. For example, a single hydrogen atom hasone electron. But a pair of hydrogen atomsshares electrons to form a covalent bond ina diatomic hydrogen molecule. Each hydrogen atom thus attains theelectron configuration of helium, a noblegas with two electrons.5Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent Bonding Combinations of atoms of the nonmetalsand metalloids in Groups 4A, 5A, 6A, and7A of the periodic table are likely to formcovalent bonds. The combined atoms usually acquire atotal of eight electrons, or an octet, bysharing electrons, so that the octet ruleapplies.6Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds The hydrogen atoms in a hydrogenmolecule are held together mainly by theattraction of the shared electrons to thepositive nuclei. Two atoms held together by sharing onepair of electrons are joined by a singlecovalent bond.7Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent BondsHydrogen gas consists ofdiatomic molecules whoseatoms share only one pairof electrons, forming asingle covalent bond.8Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds An electron dot structure such as H:H represents theshared pair of electrons of the covalent bond by twodots. The pair of shared electrons forming the covalentbond is also often represented as a dash, as in H—Hfor hydrogen. A structural formula represents the covalent bondsas dashes and shows the arrangement of covalentlybonded atoms.9Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds The halogens also form single covalent bonds intheir diatomic molecules. Fluorine is one example. By sharing electrons and forming a single covalentbond, two fluorine atoms each achieve theelectron configuration of neon.10Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds In the F2 molecule, each fluorine atomcontributes one electron to complete the octet. Notice that the two fluorine atoms share onlyone pair of valence electrons.11Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds A pair of valence electrons that is not sharedbetween atoms is called an unshared pair,also known as a lone pair or a nonbindingpair. In F2, each fluorine atom has threeunshared pairs of electrons.12Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent BondsAs you can see in the electron dotstructures below, the oxygen atom in waterhas two unshared pairs of valenceelectrons.13Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds Methane contains four single covalent bonds. 14The carbon atom has four valence electronsand needs four more valence electrons toattain a noble-gas configuration.Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent BondsEach of the four hydrogen atomscontributes one electron to share with thecarbon atom, forming four identical carbon–hydrogen bonds.15Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent Bonds 16When carbon forms bonds with otheratoms, it usually forms four bonds, as inmethane.You would not predict this pattern basedon carbon’s electron configuration, shownbelow.Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingSingle Covalent BondsThe formation of four bonds by carbon can beexplained by the fact that one of carbon’s 2selectrons is promoted to the vacant 2p orbital to formthe following electron configuration. 17This electron promotion requires only a smallamount of energy, and the stability of the resultingmethane more than compensates for the smallenergy cost.Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.1Drawing an Electron Dot StructureHydrochloric acid (HCl (aq)) isprepared by dissolving gaseoushydrogen chloride (HCl (g)) in water.Hydrogen chloride is a diatomicmolecule with a single covalent bond.Draw the electron dot structure forHCl.18Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.11 Analyze Identify the relevant concepts.In a single covalent bond, a hydrogen and achlorine atom must share a pair of electrons.Each must contribute one electron to the bond.Then show the electron sharing in thecompound they produce.19Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.12 Solve Apply concepts to the problem.Draw the electron dot structures for thehydrogen and chlorine atoms.20Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.12 Solve Apply concepts to the problem.Draw the electron dot structure for the hydrogenchloride molecule.Through electronsharing, thehydrogen andchlorine atomsattain the electronconfigurations ofthe noble gaseshelium and argon,respectively.21Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingDouble and Triple Covalent BondsAtoms form double or triple covalentbonds if they can attain a noble gasstructure by sharing two or three pairsof electrons.22Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingDouble and Triple Covalent Bonds A double covalent bond is a bond thatinvolves two shared pairs of electrons. Similarly, a bond formed by sharing threepairs of electrons is a triple covalent bond.23Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingDouble and Triple Covalent BondsThe carbon dioxide (CO2) molecule containstwo oxygens, each of which shares twoelectrons with carbon to form a total of twocarbon–oxygen double bonds.24Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingDouble and Triple Covalent Bonds Nitrogen (N2), a major component of Earth’satmosphere, contains triple bonds. A single nitrogen atom has five valenceelectrons; each nitrogen atom in the moleculemust share three electrons to have the electronconfiguration of neon.25Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingDouble and Triple Covalent Bonds You might think that an oxygen atom, with sixvalence electrons, would form a double bondby sharing two of its electrons with anotheroxygen atom. In such an arrangement, all the electronswithin the molecule would be paired.26Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingDouble and Triple Covalent Bonds Experimental evidence, however, indicatesthat two of the electrons in O2 are stillunpaired. Thus, the bonding in the oxygen molecule(O2) does not obey the octet rule.27Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The Octet Rule inCovalent BondingNitrogen and oxygen are both diatomic molecules; thetable below lists some other diatomic molecules.Diatomic ElementsNameElectron dotstructureProperties and usesF2Greenish-yellow reactive toxic gas.Compounds of fluorine, a halogen, areadded to drinking water and toothpasteto promote healthy teeth.BromineBr2Dense red-brown liquid with pungentodor. Compounds of bromine, ahalogen, are used in the preparation ofphotographic emulsions.HydrogenH2Colorless, odorless, tasteless gas.Hydrogen is the lightest known element.Fluorine28ChemicalformulaCopyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The “octet” in the octet rule refers toeight of what?29Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding The “octet” in the octet rule refers toeight of what?Each of the atoms joined by a covalentbond usually acquires eight electronsin its valence shell. Most noble gaseshave eight valence electrons.30Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent BondsCoordinate Covalent BondsHow are coordinate covalent bondsdifferent from other covalent bonds?31Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent Bonds Carbon monoxide (CO) is an example of atype of covalent bonding different from thatseen in water, ammonia, methane, andcarbon dioxide. It is possible for both carbon (which needs togain four electrons) and oxygen (which needsto gain two electrons) to achieve noble-gaselectron configurations by a type of bondingcalled coordinate covalent bonding.32Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent BondsLook at the double covalent bond betweencarbon and oxygen.With the double bond in place, the oxygenhad a stable electron configuration, but thecarbon does not.33Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent Bonds As shown below, the dilemma is solved if theoxygen also donates one of its unsharedpairs of electrons for bonding. A covalent bond in which one atomcontributes both bonding electrons is acoordinate covalent bond.34Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent BondsIn a coordinate covalent bond, theshared electron pair comes from oneof the bonding atoms.35Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent Bonds The ammonium ion (NH4 ) consists of atomsjoined by covalent bonds, including acoordinate covalent bond. A polyatomic ion, such as NH4 , is a tightlybound group of atoms that has a positive ornegative charge and behaves as a unit.36Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent BondsThe ammonium ion forms when a positivelycharged hydrogen ion (H ) attaches to theunshared electron pair of an ammoniamolecule (NH3).37Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Coordinate Covalent Bonds Most polyatomic cations and anions containcovalent and coordinate covalent bonds. Therefore, compounds containing polyatomicions include both ionic and covalent bonding.38Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.2Drawing the Electron Dot Structure of aPolyatomic IonThe H3O ion forms when a hydrogen ion isattracted to an unshared electron pair in a watermolecule. Draw the electron dot structure of thehydronium ion.39Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.21Analyze Identify the relevant concepts.Each atom must share electrons to satisfy theoctet rule.40Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.22 Solve Apply the concepts to the problem.Draw the electron dot structure of the water moleculeand the hydrogen ion. Then draw the electron dotstructure of the hydronium ion.41Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.22 Solve Apply the concepts to the problem.The oxygen must share a pair of electrons with theadded hydrogen ion to form a coordinate covalentbond.42Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Sample Problem 8.22 Solve Apply the concepts to the problem.Check that all the atoms have the electrons they needand that the charge is correct.The oxygen in the hydronium ion has eight valenceelectrons, and each hydrogen shares two valenceelectrons, satisfying the octet rule. The water molecule isneutral, and the hydrogen ion has a positive charge,giving the hydronium ion a charge of 1 .43Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Do all atoms joined in covalent bonds donateelectrons to the bond?44Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Do all atoms joined in covalent bonds donateelectrons to the bond?No. In coordinate covalent bonds, the sharedelectron pair comes from one of the bondingatoms.45Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Exceptions to the Octet RuleExceptions to the Octet RuleWhat are some exceptions to the octetrule?46Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Exceptions to the Octet RuleThe octet rule cannot be satisfied inmolecules whose total number ofvalence electrons is an odd number.There are also molecules in which anatom has less, or more, than acomplete octet of valence electrons.47Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Exceptions to the Octet Rule Two plausible electron dot structures canbe drawn for the NO2 molecule, whichhas a total of seventeen valenceelectrons. It is impossible to draw an electron dotstructure for NO2 that satisfies the octetrule for all atoms, yet NO2 does exist as astable molecule.48Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Exceptions to the Octet Rule Some molecules with an even number ofvalence electrons, such as some compounds ofboron, also fail to follow the octet rule. A few atoms, especially phosphorus and sulfur,expand the octet to ten or twelve electrons. Sulfur hexafluoride (SF6) is an example.49Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Are molecules that do not obey the octetrule necessarily unstable?50Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Are molecules that do not obey the octetrule necessarily unstable?No. There are molecules like NO2 that donot obey the octet rule, but that are stable,naturally occurring molecules.51Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Bond Dissociation EnergiesBond Dissociation EnergiesHow is the strength of a covalent bondrelated to its bond dissociationenergy?52Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Bond Dissociation Energies A large quantity of heat is released whenhydrogen atoms combine to formhydrogen molecules. This release of heat suggests that theproduct is more stable than the reactants.53Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Bond Dissociation Energies The covalent bond in the hydrogen molecule(H2) is so strong that it would take 435 kJ ofenergy to break apart all of the bonds in 1 mole(about 2 grams) of H2. The energy required to break the bondbetween two covalently bonded atoms isknown as the bond dissociation energy. The units for this energy are often given inkJ/mol, which is the energy needed tobreak one mole of bonds.54Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Bond Dissociation EnergiesA large bond dissociation energycorresponds to a strong covalentbond. A typical carbon–carbon single bond hasa bond dissociation energy of 347 kJ/mol. Strong carbon–carbon bonds help explainthe stability of carbon compounds. They are unreactive partly because thedissociation energy is high.55Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding True or False: A strong covalent bond has alow bond dissociation energy.56Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding True or False: A strong covalent bond has alow bond dissociation energy.False. A large bond dissociation energycorresponds to a strong covalent bond.57Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding ResonanceResonanceHow are resonance structures used?58Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Resonance The ozone molecule has two possible electrondot structures. Notice that the structure on the left can beconverted to the one on the right by shiftingelectron pairs without changing the positions ofthe oxygen atoms.59Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding ResonanceBecause earlier chemists imagined thatthe electron pairs rapidly flip back andforth, or resonate, between the differentelectron dot structures, they used doubleheaded arrows to indicate that two ormore structures are in resonance.60Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Resonance Double covalent bonds are usuallyshorter than single bonds, so it wasbelieved that the bond lengths in ozonewere unequal. Experimental measurements show,however, that the two bonds in ozone arethe same length. The actual bonding is a hybrid, ormixture, of the extremes represented bythe resonance forms.61Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Resonance The two electron dot structures for ozoneare examples of what are still referred toas resonance structures. Resonance structures are structuresthat occur when it is possible to draw twoor more valid electron dot structures thathave the same number of electron pairsfor a molecule or ion.62Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding ResonanceChemists use resonance structures toenvision the bonding in molecules thatcannot be adequately described by asingle structural formula. Although no back-and-forth changesoccur, double-headed arrows are usedto connect resonance structures.63Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Do resonance structures accuratelyrepresent actual bonding?64Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Do resonance structures accuratelyrepresent actual bonding?No. Resonance structures are a way toenvision the bonding in certain molecules.The actual bonding is a hybrid, or mixture,of the extremes represented by theresonance forms.65Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Key ConceptsIn covalent bonds, electron sharing occurs sothat atoms attain the configurations of noblegases.In a coordinate covalent bond, the sharedelectron pair comes from a single atom.The octet rule is not satisfied in molecules withan odd number of electrons and in moleculesin which an atom has less, or more, than acomplete octet of valence electrons.66Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Key ConceptsA large bond dissociation energycorresponds to a strong covalent bond.In ozone, the bonding of oxygen atoms isa hybrid of the extremes represented bythe resonance forms.67Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Glossary Terms single covalent bond: a bond formed whentwo atoms share a pair of electrons structural formula: a chemical formula thatshows the arrangement of atoms in a moleculeor a polyatomic ion; each dash between a pairof atoms indicates a pair of shared electrons unshared pair: a pair of valence electrons thatis not shared between atoms68Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Glossary Terms double covalent bond: a bond in which twoatoms share two pairs of electrons triple covalent bond: a covalent bond inwhich three pairs of electrons are shared bytwo atoms coordinate covalent bond: a covalent bondin which one atom contributes both bondingelectrons69Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding Glossary Terms polyatomic ion: a tightly bound group ofatoms that behaves as a unit and has apositive or negative charge bond dissociation energy: the energyrequired to break the bond between twocovalently bonded atoms; this value is usuallyexpressed in kJ per mol of substance resonance structure: one of the two or moreequally valid electron dot structures of amolecule or polyatomic ion70Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
8.2 The Nature of Covalent Bonding END OF 8.271Copyright Pearson Education, Inc., or its affiliates. All Rights Reserved.
Chapter 8 Covalent Bonding 8.1 Molecular Compounds 8.2 The Nature of Covalent Bonding 8.3 Bonding Theories 8.4 Polar Bonds and Molecules . . type of covalent bonding different from that seen in water, ammonia, methane, and carbon
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Le genou de Lucy. Odile Jacob. 1999. Coppens Y. Pré-textes. L’homme préhistorique en morceaux. Eds Odile Jacob. 2011. Costentin J., Delaveau P. Café, thé, chocolat, les bons effets sur le cerveau et pour le corps. Editions Odile Jacob. 2010. 3 Crawford M., Marsh D. The driving force : food in human evolution and the future.
