1887
Volume 2013, Issue 1
  • EISSN: 2223-506X

Abstract

A characteristic property of esters is that, they undergo both oxidation and hydrolysis under similar conditions. Furthermore, the product of each process is an aldehyde (the product of hydrolysis is alcohol, which in turn undergoes oxidation to give an aldehyde). It is, therefore, difficult to find out which process is operative. The kinetics of the reaction offers an opportunity to resolve this uncertainty. This method is illustrated in this article with two examples: oxidation of esters by Tl3+ and oxidation of esters by Co3+. The method described in this paper familiarizes students with the basic techniques involved in following the reaction, such as quenching the reaction, ensuring that the aliquots of reaction mixture are equal, taking the reaction mixture at all time intervals in an identical manner, taking infinite readings and the use of a thermostat. It also provides familiarity with the use of integrated rate equation, plotting graphs, the evaluation of slopes on graphs and the calculation of rate constants.

Loading

Article metrics loading...

/content/journals/10.5339/connect.2013.36
2013-11-01
2024-03-28
Loading full text...

Full text loading...

/deliver/fulltext/connect/2013/1/connect.2013.36.html?itemId=/content/journals/10.5339/connect.2013.36&mimeType=html&fmt=ahah

References

  1. Veda Vrath R, Sethuram B, Navneeth Rao T. Kinetics and mechanism of oxidation of aliphatic esters by Tl3+ . Indian J Chem. 1979; 17A::417.
    [Google Scholar]
  2. Deno NC, Potter NH. Mechanism of oxidation of alcohols by aqueous bromine. J Am Chem Soc. 1967; 89::35553556.
    [Google Scholar]
  3. Radhakrishnamurthy PS, Behra TC. Kinetics and mechanism of oxidation of aliphatic esters by chromic acid. J Indian Chem Soc. 1969; 46::92.
    [Google Scholar]
  4. Radhakrishnamurthy PS, Pati SC. Kinetics and mechanism of oxidation of aliphatic esters by N-bromoacetamide. J Indian Chem Soc. 1969; 46::847.
    [Google Scholar]
  5. Anand Rao M, Sethuram B, Navneeth Rao T. Kinetics and mechanism oxidation some aliphatic esters by Ce4+ . Indian J Chem. 1979; 17A::260.
    [Google Scholar]
  6. Srinivasan VS, Venkatasubramanian N. Tl3+ oxidation of esters: a kinetic study. Indian J Chem. 1979; 18::259.
    [Google Scholar]
  7. Usha AV, Sethuram B, Navneeth Rao T. Kinetics and mechanism of oxidation of aliphatic esters by Co3+ . Indian J Chem. 1979; 17A::55.
    [Google Scholar]
  8. Hammett P. Some relations between reaction rates and equilibrium constants. Chem Rev. 1953; 17::125.
    [Google Scholar]
  9. Anslyn EV, Dougherty DA. Modern physical organic chemistry. Mill Valley, CA: University Science Books 2006:p.455.
    [Google Scholar]
  10. Pavelich WA, Taft WA. The evaluation of inductive and steric effects on reactivity. The methoxide ioncatalyzed rates of methanolysis of l-menthyl esters in methanol. J Am Chem Soc. 1957; 79::4935.
    [Google Scholar]
  11. Musala Reddy P, Jagannadham V, Sethuram B, Navaneeth Rao T. Taft four parameter equation as a mechanistic tool in chromic acid oxidation of aliphatic esters. Bull Soc Chim Belg. 1982; 91:8:707712.
    [Google Scholar]
  12. Musala Reddy P, Jagannadham V, Sethuram B, Navneeth Rao T. Applicability of the Taft four parameter equation: kinetic study of chromic acid oxidation of eight o-substituted toluenes in acetic acid water mixtures. Z Phys Chem Wiesbaden. 1981;127251.
    [Google Scholar]
  13. Jagannadham V, Sethuram B, Navneeth Rao T. The evaluation of polar and steric effects on the rates of methoxide ion catalyzed condensation of some o-substituted benzaldehydes with 3,5-dimethyl-4-nitroisoxazole in methanol medium. Curr Sci. 1977; 46::704.
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journals/10.5339/connect.2013.36
Loading
/content/journals/10.5339/connect.2013.36
Loading

Data & Media loading...

  • Article Type: Research Article
Keyword(s): direct oxidation and hydrolysis and ester oxidation
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error