Ww Ley Lec (5. - Resonance > Notice two important features of these structures of carbonate ion. > First, each atom has the noble gas configuration, > Second, and this is especially important, we can convert one structure into any other by changing only the positions of the electrons, > The real carbonate ion is not represented by any of the structures 1,2 or 3 > X-Ray study of the carbonate ion shows, however, that all of their earbons- oxygen bonds are of equal length and the charge is spread equally over all three oxygen atoms. > This behavior can be explained by resonance theory. > This theory states that whenever « molecule o ion can be represented by to or more Lewis structures that differ only in the positions of the electrons, two things will be true 1, None of these structures, which \ve call resonance structures or resonance contributors, will be a correct representation for the molecule or ion. None will be in complete accord with the physical or chemical properties of the substance. 2, The actual molecule or ion will be better represented by a furbrid (average) of Mhese structures. ‘ows > One resonance contributor is converted to another by the use of curved whieh show the movement of electrons. > Thus all of the carbon—oxygen bonds of the carbonate ion are partial double bonds, and all are equivalent, > Allof them should be of the same length, and this is exactly what experiments toll us. The bonds are all /.28 long, a distance which is intermediate between that of @ carbon—oxygen single bond (1.43° A) and that of carbon—oxygen double bond (1.20° A) > Asatule, we use a solid line whenever a bond appears in all structures and a dashed line when a bond exists in one or more but not all, We also place a 8 =beside ench oxygen to indicate that something ess than a full negative charge resides on each oxygen atom Rules for Resonance: I-Individual resonance structures exist only on paper. (The position of nuclei must remain the same only electrons in multiple bonds and nonbonding electrons can be moved. (Never break a single bond when drawing resonance structures.) 2-Alll structures must be proper Lewis structures. ( The octet rule should be satisfied to the second row elements. Elements in the second row (C, N, 0, F) have only four orbitals in their valence shell.) ‘3-The energy of the actual molecule is lower than the energy of any single contributing form (The lowering of energy is called resonance stabilizatio Resonance stability rules 1-Equivalent resonance forms make equal contributions to the structure of the real molecule, 2-Unequal resonance structures contribute based on their relative stabilities. 3 When two or more structures satisfy the octet rule, the most stable one is the one with the smallest separation of oppositely charged atoms. 4- The most stable resonance form is the one in which negative charge resides on the most electronegative atom (or positive charge on the most electropositive one) A ve 5- Bach contributing Lewis structure must have the same number of electrons and the same net charge, although the formal charges of individual atoms may vary among the various Lewis structures. ‘There are five patterns that you should lear 1. A lone pair next to a pi bond, to recognize feet 2. A lone pair next to C* 3. A pi bond next to C* a ~~ [ ov <““e 4, A pi bond between two atoms, where one of those atoms is electronegative.— 5. Pi bonds going all the way around a ring, a aa yy a) Test yourself (8) (@) Write two resonance structures for the format ion HCO>’. (Note: The hydrogen and oxygen atoms are bonded to the carbon.) Explain what these structures predict (b) for the carbon—oaygen bond lengths of the formate ion and (c) for the electrical charge on the oxygen atoms. Test yourself (9) |Add curved arrows to show how the first resonance structure can be converted into the second Oe toh ~ Ay ‘ollow the curved ra ( aa > bOH-COHCH oo ff a at fy & Hy Vad a second resonance structure for each ionw 0 A :OH t ; 1 a. CHy-C~G b. CH=NH, O a H-C-H ‘Test yourself (10) CS ». O II- Prediet the hybridization of the nitrogen atom in ammonia, Draw a picture of the three dimensional structure of ammonia, and predict the bond angles. IN- Predict all bond angles in each compo VA a HA NOH c=. HECOHOH os HTABLE LO (onstatinihgeifatian | | crows | i ' | Bondedto | Orbital + Pedced | Wpesof Bonds |} Carbon | Hybridization Bond Angles. ta Carbon ‘Example Nama | wi gh aes tursimatonds ET nae | tao i | | i } omn | | et rr signtnts oe SE (20°F and ono pond ame ae “oe 7 bd 7 and two pi bonds i saeuplene we take the sum of the attached atoms to a central atom and the number of lone pairs Teahe suis them you ae gp bias, ‘Wee sum is 3 ben yuu have 8 sp eis a oe oxi aso ream Ire sm is 2. the you have 2p bits ond ts pit