January21PODkey - Please explain your reasoning clearly and...

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January 21, 2011 Problem-of-the-Day Chem 118A, Winter 2011 Shown below is "carbaglu", a drug used for the treatment of hyperammonaemia. (a) Please draw in any missing lone pairs on the structure above. (b) Please draw one valid resonance structure for this molecule. Explain why you think that the resonance structure you have drawn is likely to contribute more, less or the same amount as the structure in (a) to the overall resonance hybrid for carbaglu. (c) On the structure in part (a), please use correct curved arrows to show how to convert its electron distribution to that in the structure you've drawn in part (b). (d) To which functional group does the circled O in carbaglu belong? (e) Please identify the hybridization and geometry of the two atoms marked with 's above. (f) Which proton in carbaglu is most likely to be removed by a base?
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Unformatted text preview: Please explain your reasoning clearly and concisely. * * * N O O O N O O H H H H H H N O O O N O O H H H H H H This one is likely to contribute less, since charge is more separated (including a formal positive charge on a very electronegative oxygen). carboxylic acid tetrahedral, sp 3 trigonal planar, sp 2 The proton that is part of the lefthand carboxylic acid is most likely to be removed. This proton is attached to an oxygen atom, the most electronegative type of atom in carbaglu. The electron density left behind upon deprotonation is delocalized (stabilized) via resonance with the attached carbonyl and inductively by the electronegative carbonyl oxygen and the nearby NHR group. Note that this NHR group is closer to the lefthand COOH group than it is to the righthand one....
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