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Chapter 20: Q15P c. (page 1062)

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a)methyl salicylate

(b) methyl formate (32°C)

(c) ethyl phenylacetate

Short Answer

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(c)

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01

Synthesis of ethyl phenylacetate

(a)When phenylacetic acid is treated with an ethanol solvent and a strong acid catalyst, ethyl phenylacetate is formed along with water. This water is removed by distillation or molecular sieves.


Synthesis of ethyl phenylacetate

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Most popular questions from this chapter

Question: Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Glutathione (GSH) is a tripeptide that serves as a mild reducing agent to detoxify peroxides and maintain the cysteine residues of hemoglobin and other red blood cell proteins in the reduced state. Complete hydrolysis of glutathione gives Gly, Glu, and Cys. Treatment of glutathione with carboxypeptidase gives glycine as the first free amino acid released. Treatment of glutathione with 2,4-dinitrofluorobenzene (Sanger reagent, Problem 24-21, page 1282), followed by complete hydrolysis, gives the 2,4-dinitrophenyl derivative of glutamic acid. Treatment of glutathione with phenyl isothiocyanate does not give a recognizable phenylthiohydantoin, however.

(a) Propose a structure for glutathione consistent with this information. Why would glutathione fail to give a normal product from Edman degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis?

(b) Oxidation of glutathione forms glutathione disulfide(GSSG). Propose a structure for glutathione disulfide, and write a balanced equation for the reaction of glutathione with hydrogen peroxide.

Question: The IR spectrum of trans-oct-2-enoic acid is shown. Point out the spectral characteristics that allow you to tell that this is a carboxylic acid, and show which features lead you to conclude that the acid is unsaturated and conjugated.

Question: Draw the structures of the following compounds.

  1. propanoic acid
  2. phthalic acid
  3. calciumformate
  4. succinic acid
  5. dibromoacetic acid
  6. acetylsalicylate (aspirin)
  7. zincdecanoate (athlete's-foot powder)
  8. potassium benzoate (a food preservative)
  9. potassium fluoroacetate

Use the information in Table 4-2 to rank the following radicals in decreasing order of stability.
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