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Unformatted text preview: Notation Bruno I. Rubio 1 CH 203 O R G A N I C C H E M I S T R Y I Notation Ways of representing organic molecules The most important, interesting and useful organic molecules tend to have lots of atoms and lots of bonds. Consider the structure of the controversial drug Vioxx: C C C C C C H H S H H O O C H H H C C C O C C C C C C C H H H H H O H H Vioxx is a COX-2 inhibitor, that is, it reduces inflammation and relieves pain by inhibiting the action of the inflammation- and pain-producing enzyme cyclooxygenase-2 (COX-2). When it was revealed that long-term use of Vioxx increases the risk of heart attack, Merck, the manufacturer of Vioxx, volun- tarily withdrew Vioxx from the market despite the drugs potential of earning $2.5 billion per year in sales. Controversy centers around whether Merck knew about the adverse side effects of Vioxx before releasing the drug. Decisions by appellate courts have tended to reduce Mercks liability by overturning monetary damage awards to patients and by wholesale dismissals of class- action lawsuits leveled against the company. As big and complex as Vioxx looks, it is dwarfed by many organic molecules, some of which have tens of thousands of atoms (Vioxx has only 36). We need quick and compact ways of writing organic structures. We will now discuss the various notations used to represent organic molecules. Lewis structures In a Lewis structure every atom and every bond is explicitly shown; at the discretion of whomever is writing that Lewis structure, unshared electron pairs may be omitted. The representation of Vioxx given above is a Lewis pairs may be omitted....
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