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Chem 210-1 F08 Qz01a - like but should at some point in the...

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Chemistry 210-1 Fall 2008 1st Quiz 1. Provide the molecular formula (CnHm etc ) for compound 'A' on the right (Compound 'A') 3. From the list below, pick out ALL of the functional group classifications that apply to compound 'A' - that is, specify which functional group designations could be used in describing the structure of 'A'. alcohol aldehyde alkene alkyne amide amine aromatic carboxylic acid ether ester ketone nitrile 4. Redraw compound 'A' in a structure which includes ALL of the hydrogen atoms (you don't have to change anything else) and CIRCLE the most acidic hydrogen(s) on the structure. 5. Estimate the pKa of the hydrogen atom you've circled 6. Draw the structure of a constitutional isomer of 'A' which should be at least ten thousand times more acidic than 'A'. Your structure should also maintain the two ring systems found in 'A' (although you can move them around if you
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Unformatted text preview: like), but should at some point in the structure include at least one functional group different than those found in 'A'. Thus to get full credit your structure must a) be a constitutional isomer of 'A' b) be more acidic than 'A' by at least a factor of 10 4 c) contain the two six-membered ring systems found in 'A' and d) possess a functional group arrangement NOT found in 'A' 2. No lone pairs have been drawn in for atoms which possess them in the structure shown for compound 'A'. How many lone pairs would have to be drawn in on the structure shown to complete that structure? (You may assume no atoms are charged, and all the other assumptions for "line structures" apply). O NH 2 C 16 H 17 NO three O H 2 N CH 3 CH 3 H H H H H H H H H ~36 C C NH 2 H 3 C CH 3 O (other possible correct isomers also) The structure shown is only one of many possible correct answers - the best structures would be those isomers which possess the N-H bond of an amide ....
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