a What formal charge would the carbon atom have b What total charge would the

A what formal charge would the carbon atom have b

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(a) What formal charge would the carbon atom have? (b) What total charge would the species have? (c) What shape would you expect this species to have? (d) What would you expect the hybridization state of the carbon atom to be? 1.44) Consider a chemical species like the one in the previous problem in which a carbon atom forms three single bonds to three hydrogen atoms, but in which the carbon atom possesses an unshared electron pair. (a) What formal charge would the carbon atom have? (b) What total charge would the species have? (c) What shape would you expect this species to have? (d) What would you expect the hybridization state of the carbon atom to be? 1.45) Consider another chemical species like the ones in the previous problems in which a carbon atom forms three single bonds to three hydrogen atoms but in which the carbon atom possesses a single unpaired electron. (a) What formal charge would the carbon atom have? (b) What total charge would the species have? (c) Given that the shape of this species is trigonal planar, what would you expect the hybridization state of the carbon atom to be? 1.46) Draw a three-dimensional orbital representation for each of the following molecules, indicate whether each bond in it is a σ or π bond, and provide the hybridization for each non- hydrogen atom. Organic Chemistry Page 34
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(a) CH 2 O (b) H2C═CHCH═CH2 (c) H2C═C═C═CH3 1.47) Ozone (O 3 ) is found in the upper atmosphere where it absorbs highly energetic ultraviolet (UV) radiation and thereby provides the surface of Earth with a protective screen. One possible resonance structure for ozone is the following: (a) Assign any necessary formal charges to the atoms in this structure. (b) Write another equivalent resonance structure for ozone. (c) What do these resonance structures predict about the relative lengths of the two oxygen- oxygen bonds of ozone? (d) In the structure above, and the one you have written, assume an angular shape for the ozone molecule. Is this shape consistent with VSEPR theory? Explain your answer. 1.48) Write resonance structures for the azide ion, N3−. Explain how these resonance structures account for the fact that both bonds of the azide ion have the same length. 1.49) Write structural formulas of the type indicated: (a) bond-line formulas for seven constitutional isomers with the formula C 4 H 10 O (b) condensed structural formulas for two constitutional isomers with the formula C 2 H 7 N (c) condensed structural formulas for four constitutional isomers with the formula C 3 H 9 N (d) bond-line formulas for three constitutional isomers with the formula C 5 H 12 . 1.50) Define the relationship between the members of the following pairs. Are they constitutional isomers, the same, or something else (specify)? (a) (b) (c) (d) (e) (f) Organic Chemistry Page 35
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CHALLENGE PROBLEMS 1.51) In Chapter 15 we shall learn how the nitronium ion, NO2+, forms when concentrated nitric and sulfuric acids are mixed.
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