Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 20, Problem 20.42AP
Interpretation Introduction

Interpretation:

The method of ester synthesis by which methyl benzoate contains as much 18O label oxygen atoms is to be stated.

Concept introduction:

Diazomethane is an explosive compound having molecular formula :CH2N2+. The reaction of carboxylic acids with diazomethane gives methyl esters as the final product. This reaction is commonly termed as Wolff rearrangement.

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A student was given from the list of the compounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test?   A = haloform B = Brady     A = haloform D = Brady     B = haloform A = Brady     B = haloform D = Brady     D = haloform A = Brady     D = haloform B = Brady
Can you solve all the parts to this question Answer the following questions about the procedure: A. What would be the optical reading of (+/-)-phenylsuccinic acid (racemic phenylsuccinic acid)? B. What would you expect to be the optical reading of pure (+)-phenylsuccinic acid? [Hint: you can find this as a physical property on Sigma.] C. Explain what a reflux is. D. Why can’t you separate (+) and (-) phenylsuccinic acid using a simple recrystallization? E. After the two enantiomers are separated, how can you check the purity of the final solid (how can you determine if it is pure (+)-phenylsuccinic acid)?
(a) Illustrate the following name reactions by giving example :(i) Cannizzaro’s reaction(ii) Clemmensen reduction(b) An organic compound A contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass of the compound is 86. It does not reduce Tollen’s reagent but forms an addition compound with sodium hydrogen sulphite and gives positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acids. Derive the possible structure of compound A.
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