Camosun College Chemistry 230 Assignment # 1 Review and Preview

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1 amosun ollege hemistry 230 Assignment # 1 Review and Preview 1. or each of the following compounds, tell whether its bonds are ionic, covalent, or of both kind: Mg 2, a 3, 3 a, Br, 2 2. or each of the following compounds, draw the Lewis structures, and predict which ones will be polar: = = 3 All 3 ( 3 ) 4 ( 3 ) 2 2 =Br 3. Draw Lewis structures for the following species including all resonance structures. Assign formal charges where relevant: l l Explain what orbitals are involved in the formation of covalent bonds in: a b. 3 c. 2 = 3 d. ( 3 ) What is the hybridization of the indicated atom in each of the following compounds? Write a condensed structural formula for each compound given below: l 7. Write resonance structures for the azide ion, 3. Explain how these resonance structures account for the fact that both bonds of the azide ion have the same length (1.15 Å). 8. Based on your understanding of bonding theories, explain the following facts: a. 3 has a smaller dipole moment than does 3 b. arbon monoxide has a much smaller dipole moment than expected. c. The carboncarbon single bond in propyne is shorter than the carboncarbon single bond in propane Å 1.53 Å Using hybridized orbitals, show how σ and πbonds are formed in the following structures: a. b. 10. Explain what is meant by the terms: bonding molecular orbital and antibonding molecular orbital. how how two p orbitals combine to form two π molecular orbitals.

2 hemistry 230Answers to Assignment #1 1. Mg 2 ionic a 3 both. There are covalent bonds in the anion 3 3 a both. There are covalent bonds in the anion 3 Br covalent (Br ) 2 covalent there are 24 valence electrons. f these, 20 are used in 10 bonding pairs and 4 are used in two nonbonding pairs. Molecule is polar 2 = 2 3 molecule is nonpolar molecule is polar 3 = 3 All 3 molecule is nonploar two possible structures (cis and tran stereoisomers. The transisomer is nonploar, whereas the cisisomer is relatively nonploar) 3 l ( 3 ) 4 molecule is nonploar ( 3 ) 2 molecule is polar 2 =Br molecule is polar l l Al 3 3 l Br l 2+

3 2 2 l 3 l l l 2+ l (What is the difference between the last resonance structure and the first three structures of l 3?) a sp 3 s bond sp 3 sp 3 bond b. 3 (the two πbonds are the result of pp orbitals overlap) sp 3 s bond sps bond sp 3 sp bond spsp bond c. 2 = 3 (the πbond is the result of pp orbitals overlap) sp 2 s bond sp 2 sp 3 bond sp 2 sp 2 bond sp 3 s bond d. ( 3 ) 3 + sp 2 sp 3 bond 3 sp 3 s bond 3

4 5. The simplest way to predict the hybridization of a particular atom is to think of the electron pair geometry about that atom. 3 2 sp 3 hybridization as the electron pair geometry around the oxygen is tetrahedral sp hybridization as the electron pair geometry around the nitrogen is linear 3 3 sp 2 hybridization as the electron pair geometry around the oxygen is trigonal planar 3 3 sp 3 hybridization as the electron pair geometry around the sulfur is tetrahedral 6. ( 3 ) 2 2 ( 3 ) 2 ( 3 ) 2 ( 3 ) l 3 l The azide ion has the chemical formula 3 (a total of 16 electrons are available for the Lewis dot structure of the ion): 2 2 one of the resonance structures drawn above can represent the azide ion structure. The actual structure is a hybrid of all of them. The two bonds between the nitrogens are indistinguishable and are of the same length. They are neither single, double, nor triple, but somewhere in between (1.15 Å). Keep in mind that the nitrogennitrogen triple bond is normally 1.10 Å and the nitrogennitrogen double bond is normally about 1.20 Å. 8. a. The electronegativities of the atoms are: = 3.0, = 2.2, and = 4.0. Thus, the difference in the electronegativities of the atoms in an bond is approximately the same as the difference in the electronegativities of the atoms in an bond. owever, the dipole moment of a molecule is dependent on the vector sum of all bonds in the molecule. 3 has a smaller dipole moment than 3 because in 3 all the bond dipoles point in different directions out from the nitrogen, whereas in 3 all the bond dipoles point toward one end of the molecule.

5 b. There are 3 possible structures for, only the first one is an acceptable one since in the other two structures the octet rule is not obeyed. ince oxygen is more electronegative than carbon, we would expect polarization of the molecule towards the atom. owever, when formal charges are assigned, it becomes obvious that there is a counter effect to that polarization. The atom is assigned a formal negative charge and the atom is assigned a formal positive charge. Therefore, the polarization towards the atom is going to be reduced (that is, the end where the atom is may not be as electronegative as one would normally expect) and the molecule will have a much smaller dipole than expected. c. In order to explain the bond length, it is a good idea to figure out the hybridization schemes of the carbon atoms involved sp 3 sp 3 bond sp 3 sp bond You can immediately recognize that origins of the two bonds are different. ne is an spsp 3 bond while the other is an sp 3 sp 3 bond. There is a higher scharacter in the carboncarbon single covalent bond in propyne. ince the 2s orbital is closer to the nucleus than the 2p orbital, we would expect a bond with a higher scharacter to be a shorter bond (electrons are held more tightly by the nucleus). Therefore, the carboncarbon single covalent bond in propyne is shorter than the carboncarbon single covalent bond in propane. 9. a. 2 = 2 molecule: The carbon atoms are sp 2 hybridized. The σbond between the two carbons is an sp 2 sp 2 bond whereas the σbonds between the carbons and the hydrogens are sp 2 s bonds. bond skeleton of ethene The πbond is formed by an overlap between the remaining p orbitals (one on each carbon) b. 2 molecule:... bond Both the carbon atom and the oxygen atom are sp 2 hybridized. The σbond between the oxygen and the carbon atoms is sp 2 sp 2 bond. The bonds between the carbon and the hydrogens are sp 2 s bonds. bond skeleton of methanal

6 The πbond is formed by an overlap between the remaining p orbital on the oxygen atom and the remaining p orbital on the carbon atom.... bond 10. Bonding Molecular rbital (BM): is an orbital that results when two atomic orbitals with the same sign interact (the two atomic orbitals are said to be in phase). Electrons in a bonding orbital increase bond strength. AntiBonding Molecular rbital (ABM): a molecular orbital that results when two atomic orbitals with the opposite sign interact (the two are said to be out of phase). Electrons in an antibonding orbital decrease bond strength. interf erence * antibonding molecular orbital (higher in energy) reinf orcement bonding molecular orbital (lower in energy)

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