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Carbon has four valence electrons, no dots, and three sticks: Formal charge on C = 4 – 0 – 3 = +1. qxp 34 5/27/08 9:55 AM Page 34 Part I: The Fundamentals of Organic Chemistry Using the scanning method, look for atoms that have a number of bonds different from neutral form. For example, carbon has four bonds when neutral, so look for carbons that have anything other than four bonds. The left-most carbon has three bonds and a lone-pair, so this atom has a charge. Looking at the patterns shown in Figure 2-1, this configuration is for a negativelycharged carbon.

P H 1s sp p C p sp sp p C p sp H 1s This problem is daunting, but you can tackle it step by step. The first thing to do is determine the hybridizations for all the atoms. The two carbons are sp hybridized. The hydrogens, having only one electron, remain unhybridized (hydrogen is the only atom that doesn’t rehybridize in organic molecules): H 1s sp p C p sp sp p C sp H 1s Next, you need to figure out which orbitals overlap to give rise to the bonds in acetylene. The C-H bonds form from overlap of the hydrogen 1s orbitals with the sp orbitals on carbon.

Draw the other resonance structures for the following cationic molecule by arrowpushing. After you’ve drawn all the resonance structures, draw what the actual structure of the molecule looks like, including charges. H C H C H C H H A. H C H C H C H resonance structure H H H C H C C H H resonance structure 1. H H +½ +½ C C H C H H actual structure Draw the resonance structure for the following molecule by using arrow-pushing. After you’ve drawn the resonance structure, sketch what the actual structure looks like, including charges.

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