Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Textbook Question
Chapter 5, Problem 1E
Occasionally, we will see an ionic compound that has a
a. What elements (other than H) on the periodic table are most likely to form a
b. Draw a Lewis structure for the ionic compound
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Draw Lewis structure(s) for the carbonate lon (CO₂). If there are equivalent resonance structures, draw all of them.
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Do not include overall lon charges or formal charges in your drawing.
Do not draw double bonds to oxygen unless they are needed in order for the central atom to obey the octet rule.
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4. Draw the Lewis structure of the ozonide ion, O32−. (Assign lone pairs, radical electrons, and atomic charges where appropriate.)
2. Avogadro does not "waste" his time drawing a Lewis structure before
determining the shape of PF3. He thinks that the shape of PF3 must be trigonal
planar because there are three fluorine atoms bonded to the central
phosphorus atom.
a. Draw the Lewis structure for PF3.
b. Was Avogadro's answer for the shape of a PF3 molecule correct? Explain
c. Why is it important to draw the Lewis structure for a molecule before
identifying the shape of the molecule?
Chapter 5 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 5 - Which elements on the periodic table (other than...Ch. 5 - You will not find “hydroxide” in the stockroom,...Ch. 5 - Prob. 3CTQCh. 5 - Prob. 4CTQCh. 5 - Prob. 5CTQCh. 5 - Prob. 6CTQCh. 5 - On which do you expect to have a more intense and...Ch. 5 - Prob. 8CTQCh. 5 - Prob. 9CTQCh. 5 - Prob. 10CTQ
Ch. 5 - Prob. 11CTQCh. 5 - Prob. 12CTQCh. 5 - Prob. 13CTQCh. 5 - Prob. 14CTQCh. 5 - Prob. 15CTQCh. 5 - Prob. 16CTQCh. 5 - For each proposed set of resonance structures: a....Ch. 5 - Consider the polarization of the C=O bond in the...Ch. 5 - The C=O double bond is called a “carbonyl bond.”...Ch. 5 - Prob. 20CTQCh. 5 - Prob. 21CTQCh. 5 - Prob. 22CTQCh. 5 - Prob. 23CTQCh. 5 - Prob. 24CTQCh. 5 - Prob. 25CTQCh. 5 - Prob. 26CTQCh. 5 - Prob. 27CTQCh. 5 - Prob. 28CTQCh. 5 - Prob. 29CTQCh. 5 - Prob. 30CTQCh. 5 - Prob. 31CTQCh. 5 - Confirm that there is no legitimate Lewis...Ch. 5 - Draw all resonance structures of the molecule...Ch. 5 - Prob. 34CTQCh. 5 - Prob. 35CTQCh. 5 - Prob. 36CTQCh. 5 - Occasionally, we will see an ionic compound that...Ch. 5 - Prob. 2ECh. 5 - Prob. 3ECh. 5 - Prob. 4ECh. 5 - Is it possible to draw a resonance structure of...Ch. 5 - Prob. 6ECh. 5 - Prob. 7ECh. 5 - Prob. 8ECh. 5 - Phenol (shown below) has a pKa10 . a. Based on pKa...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Prob. 12ECh. 5 - Complete each Lewis structure, draw all important...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Construct an explanation for why sulfuric acid is...Ch. 5 - Prob. 16ECh. 5 - Prob. 17ECh. 5 - Prob. 18E
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- Bond Enthalpy When atoms of the hypothetical element X are placed together, they rapidly undergo reaction to form the X2 molecule: X(g)+X(g)X2(g) a Would you predict that this reaction is exothermic or endothermic? Explain. b Is the bond enthalpy of X2 a positive or a negative quantity? Why? c Suppose H for the reaction is 500 kJ/mol. Estimate the bond enthalpy of the X2 molecule. d Another hypothetical molecular compound, Y2(g), has a bond enthalpy of 750 kJ/mol, and the molecular compound XY(g) has a bond enthalpy of 1500 kJ/mol. Using bond enthalpy information, calculate H for the following reaction. X2(g)+Y2(g)2XY(g) e Given the following information, as well as the information previously presented, predict whether or not the hypothetical ionic compound AX is likely to form. In this compound, A forms the A+ cation, and X forms the X anion. Be sure to justify your answer. Reaction: A(g)+12X2(g)AX(s)The first ionization energy of A(g) is 400 kJ/mol. The electron affinity of X(g) is 525 kJ/mol. The lattice energy of AX(s) is 100 kJ/mol. f If you predicted that no ionic compound would form from the reaction in Part e, what minimum amount of AX(s) lattice energy might lead to compound formation?arrow_forwardThe chemistry of the nitrite ion and HNO2: (a) Two resonance structures are possible for NO2. Draw these structures, and then find the formal charge on each atom in each resonance structure. (b) In forming the acid HNO2 an H+ ion attaches to the O atom and not the N atom of NO2. Explain why you would predict this result. (c) Two resonance structures are possible for HNO2. Draw these structures, and then find the formal charge on each atom in each resonance structure. Is either of these structures strongly preferred over the other?arrow_forwardThis Lewis structure for SF5+ is drawn incorrectly. What error was made when determining the number of valence electrons?arrow_forward
- Draw resonance structures for the SO2 molecule, and determine the formal charges on the S and O atoms. Are the SO bonds polar, and is the molecule as a whole polar? If so, what is the direction of the net dipole in SO2? Is your prediction confirmed by the electrostatic potential surface? Explain briefly.arrow_forwardLewis structures can be used to understand why some molecules react in certain ways. Write the Lewis structures for the reactants and products in the reactions described below. a. Nitrogen dioxide dimerizes to produce dinitrogen tetroxide. b. Boron trihydride accepts a pair of electrons from ammonia, forming BH3NH3. Give a possible explanation for why these two reactions occur.arrow_forwardDefine the term lattice energy. Why, energetically, do ionic compounds form? Fig. 3-8 illustrates the energy changes involved in the formation of MgO(s) and NaF(s). Why is the lattice energy of MgO(s) so different from that of NaF(s)? The magnesium oxide is composed of Mg2+ and O2 ions. Energetically, why does Mg2+O2 form and not Mg+O? Why doesnt Mg3+O3 form?arrow_forward
- The equation for the combustion of gaseous methanol is 2 CH3OH(g) + 3 O2(g) 2 CO2(g) + 4 H2O(g) (a) Using the bond dissociation enthalpies in Table 8.8, estimate the enthalpy change for this reaction. What is the enthalpy of combustion of one mole of gaseous methanol? (b) Compare your answer in part (a) with the value of tHcalculated using enthalpies of formation data.arrow_forwardBest Lewis Formula and Molecular Geometry A student writes the Lewis electron-dot formula for the carbonate anion, CO32, as a Does this Lewis formula obey the octet rule? Explain. What are the formal charges on the atoms? Try describing the bonding for this formula in valence bond terms. Do you have any difficulty doing this? b Does this Lewis formula give a reasonable description of the electron structure, or is there a better one? If there is a better Lewis formula, write it down and explain why it is better. c The same student writes the following resonance description for CO2: Is there something wrong with this description? (What would you predict as the geometries of these formulas?) d Is one or the other formula a better description? Could a value for the dipole moment help you decide? e Can you write a Lewis formula that gives an even better description of CO2? Explain your answer.arrow_forwardFor each of the following, use formal charges to choose the Lewis formula that gives the best description of the electron distribution: a ClO2F b SO2 c ClO3arrow_forward
- a. How many sticks did you need to make the skeleton structure?____________ b. How many sticks are left over? ____________ If your model is to obey the octet rule, each ball must have four sticks in it except for hydrogen atom balls, which need and can only have one. Each atom in an octet rule species is surrounded by four pairs of electrons. c. How many holes remain to be filled? ____________ Fill them with the remaining sticks, which represent nonbonding electron pairs. Draw the complete Lewis structure for NH2Cl using lines for bonds and pairs of dots for nonbonding electrons.arrow_forwardLight of appropriate wavelength can break chemical bonds. Light having λ < 240 nm can dissociate gaseous O2. It requires light with λ < 819 nm to dissociate gaseous H2O2 to 2 OH. Assume that all of the photon energy is used solely for these dissociations. (a) Calculate the energy required to dissociate (i) O2 and (ii) H2O2. (b) Consider the results of part (a). How well do they correlate with the Lewis structures of O2 and H2O2? Explain your answer.arrow_forwardCompare the electron dot structures of the carbonate (CO32) and borate (BO33) ions. (a) Are these ions isoelectronic? (b) How many resonance structures does each ion have? (c) What are the formal charges of each atom in these ions? (d) If an H+ ion attaches to CO32 to form the bicarbonate ion, HCO3, does it attach to an O atom or to the C atom?arrow_forward
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