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1 Chemical Bonding Outline 1. Lewis Dot Structures 2. Bonds 3. Formal Charges 4. VSEPR (Molecular Geometry and Hybridzation) 5. Common Resonance Structures and Dimerization Review 1. Lewis Dot Structures Count total # of e- Lone atom in center, fill the outside atoms with octets Add left over e- to the center atom If there is less than an octet on the center atom move outer e- to multiple bonds 2. Bonds Stronger Bonds < = < Longer Bonds < = < Single Bond: σ (1 sigma) (bond order = 1) Double Bond: σ and π (1 sigma and pi) (bond order = 2) Triple Bond: σ and 2π (1 sigma and 2 pi) (bond order = 3) 3. Formal Charges Valence e Subtract e- Assigned to atom Formal Charge This CO 2 chosen b/c of 0 FC
2 4. VSEPR (Molecular Geometry and Hybridization) Bonding Sites Hybridization Shape Bond Angle Example 1 or 2 sp Linear 180 HF, CO 2 3 sp 2 Trigonal Planar 120 BCl 3 Bent < 120 SO 2 4 sp 3 Tetrahedral CH 4 Trigonal Pyramidal 107 NH 3 Bent 105 H 2 O 5 sp 3 d Trigonal Bipyramidal 90 /120 PCl 5 Seesaw 90 /<120 SF 4 T-Shaped 90 ClF 3 Linear 180 XeF 2 6 sp 3 d 2 Octahedral 90 SF 6 Square Pyramidal 90 BrF 5 Square Planar 90 XeF 4 Note: Trigonal Bipyramidal loses atoms off the equatorial Octahedral loses atoms off the axial More than an octet and noble gases able to bond due to adding e- to empty d orbitals
3 5. Common Resonance Structures and Dimerization NO 2 Dimerization into N 2 O 4 SO 2 O 3 (ozone) NO 3 - (nitrate) C 6 H 6 (Benzene) Note: Bond lengths of resonance structures are all the same, but are averages. Example: NO 2 has a bond order of 1.5 (single bond = 1, double bond = 2).
4 Chemical Bonding Problem Set Lewis Dot Structures Bonds 1. Write Lewis structures for the following (show resonance if present): a. SiH 4 b. CO c. SF 2 d. SO 4 2- e. ClO 2 - f. NH 2 NH 2 2. Write Lewis structures for the following (show resonance if present): a. H 2 O 2 b. SO 2 c. SO 3 d. CO 2 e. IO 3 - f. XeF 2 3. Which of the following molecules will have a Lewis dot structure with exactly one unshared electron pair on the central atom? (A) H 2 O (B) PH 3 (C) PCl 5 (D) CH 2 Cl 2 (E) BeCl 2 4. Based on Lewis dot structures, predict the ordering of N-O bonds lengths in NO +, NO 2 -, and NO 3 -. What can be stated about the bond strengths? Assign oxidation numbers for all nitrogen atoms in each molecule. 5. Draw three possible resonance structures of ClO 2. Use formal charges to select the resonance structure(s) that is (are) most important. 6. Draw acetic acid, CH 3 COOH (structural formula) so that the octet rule is satisfied. Total all sigma and pi bonds in this molecule. VSEPR (Molecular Geometry and Hybridization) Questions 7-9 (A) BF 3 (B) CO 2 (C) H 2 O (D) CF 4 (E) PH 3 7. The central atom in this molecule forms sp 2 hybrid orbitals. 8. This molecule has a trigonal pyramidal structure.
5 9. This molecule has a linear structure.
6 10. Which of the following species does NOT have a tetrahedral structure? (A) CH 4 (B) NH 4 + (C) SF 4 (D) AlCl 4 - (E) CBr A molecule whose central atom has d 2 sp 3 hybridization can have which of the following shapes? I. Tetrahedral II. Square pyramidal III. Square planar (A) I only (B) III only (C) I and II only (D) II and III only (E) I, II, and III 12. Draw each Lewis structure and predict the molecular geometries and hybridization of each molecule: a. PF 3 b. BrF 3 c. XeF 2 d. HCN e. CH Draw each Lewis structure and predict the molecular geometries and hybridization of each molecule: a. SF 4 b. NO 2 c. XeF 4 d. H 2 S e. BrF Determine the bond angles of the molecules, NH 4 +, NH 3, and NH 2 -, and explain the variation. 15. The molecules BrF 4 - and CF 4 both have central atoms bonded to four fluorine atoms. Determine if the geometries of these molecules are two or three dimensional. Justify your answer. Name another molecule that could be bonded to four fluorine atoms that would be a different hybridization than those listed. 16. The molecules XeF 2, H 2 O, and CO 2 all have central atoms bonded to two atoms. Show both similarities and differences in terms of two or three dimensionality and hybridizations. 17. The three structures above show three possible shapes of an AF 3 molecule. Predict which of the following elements could represent A as the central atom in these shapes: B, C, P, S, Br, or Kr.
7 Common Resonance Structures and Dimerization 18. The six carbon atoms in a benzene molecule are shown in different resonance forms as three single bonds and three double bonds. If the length of a single carbon-carbon bond is 154 pm and the length of a double carboncarbon bond is 133 pm, what length would be expected for the carbon-carbon bonds in benzene? (A) 126 pm (B) 133 pm (C) 140 pm (D) 154 pm (E) 169 pm 19. The compound above is acetylsalicylic acid, or aspirin. Using the molecule above determine: a. The hybridization around the carbon atoms that have an arrow with assigned numbers. b. The bond angles of the carbon atoms that have an arrow with assigned numbers. c. The bond angles of the C-O-H and C-O-C bonds, respectively. d. The total number of sigma and pi bonds in the entire molecule. e. Show one example of resonance of the molecule above. 2 NO 2 (g) N 2 O 4 (g) 20. Nitrogen dioxide can form dinitrogen tetroxide in the equilibrium reaction given above. a. What is this process called? b. What can be said about the molar masses of these molecules? c. Show the Lewis structures and how this reaction occurs. d. Why is nitrogen dioxide paramagnetic whereas dinitrogen tetroxide diamagnetic? e. Which substance is a colorless gas and which is a brown gas? Free Response 21. The carbonate ion CO 3 2- is formed when carbon dioxide, CO 2, reacts with slightly basic cold water. (a) Draw the Lewis electron dot structure for the carbonate ion. Include resonance forms if they apply. (b) Draw the Lewis electron dot structure for carbon dioxide. (c) Describe the hybridization of the carbon in the carbonate ion. (d) Describe the relative lengths of the three C-O bonds in the carbonate ion. (e) Compare the average length of the C-O bonds in the carbonate ion to the average length of the C-O bonds in carbon dioxide. (f) How many sigma and pi bonds are there in the carbonate ion, CO 3 2-? 22. Given the three molecules, CF 4, PF 5, and SF 4, complete the following questions relating to chemical bonding. (a) Draw the complete Lewis structure (electron-dot structure) for the molecules CF 4, PF 5, and SF 4. (b) What is the F-C-F bond angle in CF 4? (c) What is the hybridization of the valence orbitals of P in PF 5? (d) What is the geometric shape formed by the atoms in SF 4?
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