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Ch.9 - Chemical Bonding I: The Lewis Model
Chapter 9, Problem 96

Phosgene (Cl2CO) is a poisonous gas used as a chemical weapon during World War I. It is a potential agent for chemical terrorism today. Draw the Lewis structure of phosgene, including all three resonance forms by alternating the double bond among the three terminal atoms. Which resonance structure is the best?

Verified step by step guidance
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<insert step 1> Start by counting the total number of valence electrons in phosgene (Cl2CO). Chlorine has 7 valence electrons, carbon has 4, and oxygen has 6. Therefore, the total number of valence electrons is 2(7) + 4 + 6 = 24 valence electrons.>
<insert step 2> Draw a skeletal structure with carbon as the central atom, since it is less electronegative than oxygen and chlorine. Connect the carbon atom to the two chlorine atoms and the oxygen atom with single bonds.>
<insert step 3> Distribute the remaining valence electrons to satisfy the octet rule for each atom. Start by placing lone pairs on the terminal atoms (Cl and O) to complete their octets.>
<insert step 4> Consider the possibility of resonance structures by moving a lone pair from the oxygen atom to form a double bond with the carbon atom. This will create a resonance structure. Repeat this process by forming a double bond between carbon and each chlorine atom, one at a time, to generate all possible resonance structures.>
<insert step 5> Evaluate the resonance structures based on formal charges. The best resonance structure is the one where the formal charges are minimized and the negative charge, if any, is on the most electronegative atom. Calculate the formal charges for each atom in all resonance structures to determine the most stable one.>
Related Practice
Textbook Question

The reaction of Fe2O3(s) with Al(s) to form Al2O3(s) and Fe(s) is called the thermite reaction and is highly exothermic. What role does lattice energy play in the exothermicity of the reaction?

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Textbook Question

NaCl has a lattice energy of -787 kJ/mol. Consider a hypothetical salt XY. X3+ has the same radius of Na+ and Y3- has the same radius as Cl-. Estimate the lattice energy of XY.

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Open Question
Draw the Lewis structure for nitric acid, ensuring the hydrogen atom is attached to one of the oxygen atoms. Include all three resonance structures by alternating the double bond among the three oxygen atoms. Use formal charge to determine which of the resonance structures is most important to the structure of nitric acid.
Textbook Question

The cyanate ion (OCN-) and the fulminate ion (CNO-) share the same three atoms but have vastly different properties. The cyanate ion is stable, while the fulminate ion is unstable and forms explosive compounds. The resonance structures of the cyanate ion are explored in Example 9.8. Draw Lewis structures for the fulminate ion—including possible resonance forms— and use formal charge to explain why the fulminate ion is less stable (and therefore more reactive) than the cyanate ion.

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Textbook Question

Draw the Lewis structure for each organic compound from its condensed structural formula. b. CH3OCH3

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Textbook Question

Draw the Lewis structure for each organic compound from its condensed structural formula. c. CH3COCH3

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