Problem_Set_1

Problem_Set_1 - magnitude, such that it will generally be...

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Organic Chemistry c3046y Problem Set 1 - Carboxylic Acids and Derivatives, and Interconversions Thereof Due in class on Monday, February 4 Relevant Book Problems (Chap. 16): 48, 53, 58, 59, 62, 63, 71, 76, 77, 79. Relevant Reading: Chapter 16. N N O O CH 2 CH 3 N O CH 2 CF 3 A B C 2. Rank the three compounds shown below from lowest frequency to highest frequency for the C=O stretch in the IR spectra. R O H O Cl Cl O O R Cl O In class, we discussed how acid chlorides may be prepared by treating a carboxylic acid with SOCl 2 . Here is another that employs oxalyl chloride. + + CO 2 + HCl Although this is a nice way to make acid chlorides, the reaction can be rather slow requiring 12 hours or more. It has been found that the addition of a catalytic amount of DMF catalyzes this reaction by several orders of
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Unformatted text preview: magnitude, such that it will generally be done in less than 15 min. + CO 1. ~12 h. R O H O Cl Cl O O H N Me Me O R Cl O + ( N,N-Dimethylform-amide or DMF) Catalytic Amount of: + CO 2 + HCl + CO < 15 min. H N Me Me O Cl Cl O O H N Cl Me Me Cl-+ The DMF first reacts with the oxalyl chloride as follows: b. Write a plausible mechanism for this transformation. + CO 2 + CO R O H O R Cl O H N Cl Me Me Cl-H N Me Me O In the second part of the reaction, the following reaction occurs, and the DMF is regenerated: + + c. Write a plausible mechanism for this transformation. ( Oxalyl Chloride) a. Write a plausible mechanism for this transformation. + HCl...
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This note was uploaded on 04/16/2008 for the course CHEM C3046 taught by Professor Leighton during the Spring '08 term at Columbia.

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