Unformatted text preview: 1. Squaric acid (below) is a very acidic organic compound. Chem 322a 9/8/10 a. Using resonance structures, explain why squaric acid is more acidic than cyclobutanol. O HO O OH b as e s qu ar ic ac id b as e OH cy c lob utano l b. Draw all four resonance structures for the dianion of squaric acid. Would you expect this second proton to also be acidic? O HO 2. (6 pt) Write the functional group of each of these compounds underneath their structures, including 1°, 2° or 3° as appropriate. H N Br OH O O b as e 1 3. Write an equation for the Lewis acid/Lewis base reaction between boron trifluoride and dimethyl sulfide (CH3)2S. Show formal charges if present and use curved arrows to track the flow of electrons. 4. Provide a plausible synthesis for this molecule using any necessary reagents. OH 5. Order the following from strongest to weakest acid. OT D H O N OH H N H N a. b. c. d. e. (most acidic) a. > d. > c. > e. > b. (least acidic) 2 6. For each of these 5 reactions, fill in the boxes with the correct arrow indicating the direction of the equilibrium and circle the stronger acid. a) CH3CH2 S ++
H3 C S SH CH3CH2SH S +
H3 C S - b) P H3 ++ +
++ AsH2 - + PH2 - + AsH3 c) H2Te -SH -TeH + H2S O
d) Cl3C S
e) O - ++ +
H3 C O OH Cl3C O OH +
H3 C O O - S ++ + S S S S + - 7. Indicate which acidity trend (for example, “bond strength”) you applied to answer a) through e) in question 6. a) _________________________ b) _________________________________ c) ______________________________ d) ______________________________________ e) ______________________________________ 3 ...
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This note was uploaded on 10/18/2010 for the course CHEM 322 A taught by Professor Bertolini during the Spring '10 term at USC.
- Spring '10
- Organic chemistry