PS8_2011Ans - Name Ch 1b, Problem Set Eight SOLUTIONS...

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Unformatted text preview: Name Ch 1b, Problem Set Eight SOLUTIONS Section Side 1 of 10 Due Friday, Mar. 4, 2011 Rec TA at 4 PM PST in the Drop Box 1. Acid-Base Chemistry (15 points) Consider the polyfunctional compounds shown below. What would you expect to be the site of ( i ) protonation and ( ii ) deprotonation if each compound was treated with a suitable acid or base. In each case, suggest a suitable acid or base for both purposes. Solutions 2 pts. for each protonation/deprotonation product 0.5 pts. for each acid/base used o For the protonation step, any strong acid (e.g., H 2 SO 4 , HCl, etc.) is acceptable. o For deprotonation step, alkyl amines, alkyl lithiums, etc. are acceptable. (c) is rather acidic (thiophenol pK a ~ 7), so judge bases accordingly. Give credit for hydroxide; however, the pK a of these alcohols are ~15, while H 2 O pK a is ~15 as well. Name Ch 1b, Problem Set Eight SOLUTIONS Section Side 2 of 10 Due Friday, Mar. 4, 2011 Rec TA at 4 PM PST in the Drop Box 2. Carbonyl Addition Reactions (17 points) Provide the products of the following reactions. For parts (b), (c), and (d) provide the curved arrow mechanism for each step of the reaction. Solutions Name Ch 1b, Problem Set Eight SOLUTIONS Section Side 2 of 10 Due Friday, Mar. 4, 2011 Rec TA at 4 PM PST in the Drop Box 2. Carbonyl Addition Reactions (17 points) Provide the products of the following reactions. For parts (b), (c), and (d) provide the curved arrow mechanism for each step of the reaction. Solutions Name Ch 1b, Problem Set Eight SOLUTIONS Section Side 3 of 10 Due Friday, Mar. 4, 2011 Rec TA at 4 PM PST in the Drop Box H 3 C CH 3 H 3 C O N H H H 3 C CH 3 H 3 C OH N H OH 2 H H 3 H 3 C H 3 C CH 3 N H H 2 O H 3 C CH 3 CH 3 N Primary amines give imine products (as mixture of imine geometries) 3 H 2 O Part (a): 2 points for product Part (b): 5 points total; 2 points for product, 3 points for curved arrow mechanism Part (c): 5 points total; 2 points for product, 3 points for curved arrow mechanism Part (d): 5 points total; 2 points for product, 3 points for curved arrow mechanism NOTE TO GRADERS: the curved arrow mechanisms shown above are suggestions. Some students may start their mechanisms with a resonance structure moving electrons from the carbonyl double bond to the carbonyl oxygen, for example, and that is perfectly fine. In the mechanisms above, this particular movement of electrons is indicated as reacting simultaneously with attack at the carbonyl carbon. Both versions are correct. Also, protonation can often occur from an outside water (solvent) or from an acid molecule. Either of these mechanisms of protonation is acceptable. As long as the student shows understanding of the underlying mechanism (nucleophilic attack at the carbonyl carbon and subsequent hydrolysis, etc.), full credit should be received. Labels such as tetrahedral intermediate are explanatory and are not necessary for full credit. Name...
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This note was uploaded on 03/21/2011 for the course CHEMISTRY 1b taught by Professor Reisman;heath during the Winter '11 term at Caltech.

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PS8_2011Ans - Name Ch 1b, Problem Set Eight SOLUTIONS...

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