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5° Methanol (methyl alcohol) Phosphorus and sulfur are the third-row analogs of nitrogen and oxygen, and the bonding in both can be described using hybrid orbitals. Because of their positions in the third row, however, both phosphorus and sulfur can expand their outer-shell octets and form more than the typical number of co­valent bonds. Phosphorus, for instance, often forms five covalent bonds, and sulfur often forms four. Phosphorus is most commonly encountered in biological molecules in organophosphates, compounds that contain a phosphorus atom bonded to four oxygens, with one of the oxygens also bonded to carbon.

Ethane, C2H6, is the simplest molecule containing a carbon–carbon bond. H H H C C H H H H H H C C H H H CH3CH3 Some representations of ethane We can picture the ethane molecule by imagining that the two carbon atoms bond to each other by s overlap of an sp3 hybrid orbital from each (Figure 1-12) . The remaining three sp 3 hybrid orbitals on each carbon overlap with the 1s orbitals of three hydrogens to form the six C ] H bonds. The C ] H bonds in ethane are similar to those in methane, although a bit weaker—421 kJ/mol (101 kcal/mol) for ethane versus 439 kJ/mol for methane.

All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. xxviii Preface • The new Practice Your Scientific Analysis and Reasoning feature provides two-page essays and corresponding professional exam-style questions on special topics related to medical, pharmaceutical, and biological applications of organic chemistry.

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