Practice Test 2

Practice Test 2 - 1 Squaric acid(below is a very acidic...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

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 ...
View Full Document

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.

Ask a homework question - tutors are online