Second Order Rate Constant of Water Assisted Neutral Hydrolysis of Methyl Acetate: Project Based Activity for Post Graduate Students

Mallelli Murali¹, Sanjeev Rachuru^2, , Jagannadham Vandanapu^3, , M. Sujatha², K B Shanti Sudha⁴, Devarkonda A. Padmavathi³ and Adam A Skelton⁵

¹Department of Chemistry, Geethanjali College of Engineering and Technology, Cheeryal-501301, Telangana, India

²Department of Chemistry, St. Ann's College for Women, Mehdipatnam, Hyderabad 500 028, Telangana, India

³Department of Chemistry, Osmania University, Hyderabad-500007, India

⁴Department of Chemistry, Govt. Degree College for Women, Begumpet, Hyderabad 500016, Telangana, India

⁵Department of Pharmacy, School of Health Science, University of KwaZulu-Natal, Durban 4000, South Africa

Cite this paper:
Mallelli Murali, Sanjeev Rachuru, Jagannadham Vandanapu, M. Sujatha, K B Shanti Sudha, Devarkonda A. Padmavathi and Adam A Skelton. Second Order Rate Constant of Water Assisted Neutral Hydrolysis of Methyl Acetate: Project Based Activity for Post Graduate Students. World Journal of Chemical Education. 2025; 13(4):98-102. doi: 10.12691/wjce-13-4-2

Abstract

There were numerous reports on the kinetic study of acid catalyzed hydrolysis of methyl acetate. In all these studies emphasis was on the calculation of pseudo-first order rate constant. There were very few reports on the calculation of second order rate constant of uncatalyzed hydrolysis of methyl acetate; a small note regarding the second order rate constant is mentioned in the 12^th class Central Board of Secondary Education (CBSE) Indian textbook. It is known that the hydrolysis of methyl acetate can proceed via two pathways: the un-catalyzed and the acid catalyzed. The un-catalyzed path of the reaction is too slow to be followed. It will take several days to follow the reaction. In the present article an attempt was made to calculate the second order rate constant of the un-catalyzed path. This rate constant was obtained by plotting k_obs (pseudo-first order acid catalyzed rate constants at different acid concentrations) versus [H⁺]. The extrapolation to zero concentration that is the y-intercept divided by the water concentration yields the second order un-catalyzed rate constant. This second order rate constant was also determined theoretically. To the best of our knowledge, no one has determined the second order rate constant of this uncatalyzed reaction. This can be given as project-based activity to Graduate students.

Keywords:
Methyl acetate Second order DFT

This work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References:

[1]	Wilhelmy Ludwig F. Ueber das Gesetz, nach welchem die Einwirkung der Säuren auf den Rohrzucker stattfindet. Annalen der Physik und Chemie 1850, 81, 413-433.
[2]	Ostwald W. Studien zur chemischen D ynamik; Die Einwirknng der Sauren auf Hethylacetat. J. prakt. Chem. 1883, 28, 449-495.
[3]	Griffith, R. O., McCullagh Lewis, W. C. Studies in catalysis. Part IV. Stoichiometric and catalytic effects due to the progressive displacement of one reactant by another in the “acid” hydrolysis of methyl acetate. J. Chem. Soc. 1916, 109, 67-83.
[4]	Harned, H. S.; Pfansteil, R. A study of the velocity of hydrolysis of ethyl acetate. J. Am. Chem. Soc 1922, 44, 2193-2205.
[5]	Harned, H. S.; Samaras Nicholas, N. T. The effect of change of medium upon the velocity of hydrolysis of ethyl orthoformate. J. Am. Chem. Soc 1932, 54, 1-8.
[6]	Tommila E.; Hinshelwood C. N. The activation energy of organic reactions. Part IV. Transmission of substituent influences in ester hydrolysis. J. Chem. Soc 1938, 1801-1810.
[7]	Poethke W.Ber Über die Ester-Hydrolyse in reinem Wasser. 1935, 68.6,1031-1037.
[8]	Friedman, H. B.; Elmore, G. V. The hydrolysis of Methyl acetate in a Non-Aqueous solvents. J. Am. Chem. Soc 1941, 63, 864-867.
[9]	Skrabal A, Zahorka A. Die Wasserverseifung des Äthylazetats. Monatsh. Chem., 1929, 53-54, 562-567.
[10]	Mata Segreda, J. F. Spontaneous hydrolysis of ethyl formate: Isobaric Activation Parameters. Int. J. Chem. Kinet., 2000, 32, 67-71.
[11]	Hammett Louis, P. Some Relations between Reactions Rates and Equilibrium Constants.Chem. Rev. 1935, 17, 1, 125-136.
[12]	Jagannadham V. Kinetics experiments in the undergraduate chemistry laboratory. Mistakes and measures: Kinetics of acid catalyzed hydrolysis of methyl acetate as an example Khimiya/Chemistry 2010, 19, 114.
[13]	Hsieh Yih Huang.; Noham Weinberg.; Wolfe Saul. The Neutral Hydrolysis of Methyl Acetate -Part 1. Kinetic Experiments. Canadian Journal of Chemistry 2009, 87, 539-543.
[14]	Ikhazuangbe.; Ohien, P. M.; Babalola,O. Reaction rate and rate constant of the hydrolysis of ethyl acetate with sodium hydroxide. American Journal of Scientific and Industrial Research 2015, 6, 1-4.
[15]	BeezerA. E.; Steenson,T. I; Tyrell, H.J.V. Kinetic studies in a flow microcalorimeter the acid-catalysed hydrolysis of methyl acetate at 25oC. Tyrrell H. J. V. Thermochimica Acta 1974, 9, 4, 447-449.
[16]	Ehteshami, M.; Rahimi, N.; Eftekhari, A. A.; NasrM. J. Kinetic study of catalytic hydrolysis reaction of methyl acetate to acetic acid and methanol. Journal of Science & Technology, Transaction B, Engineering 2006, 30, 595-606.
[17]	https:// www.brainkart.com/article/ Determination-of-rate-constant-of -acid-catalysed -hydrolysis-of-an-ester_2882/.
[18]	http:// www.satyensaha.com/ pdf%20files/ B.Sc.%201st% 20year-Ester-hydrolysis -Practical S Saha.pdf.
[19]	Nair P. Madhavan.; Anantakrishnan, S. V. Proc. Indian Acad. Sci. (Math. Sci.). 1950, 32.
[20]	Khandrewal, B. L. Chemistry Part I, An Indian text book meant for the curriculum of Central Board of Secondary Education, New Delhi, India, Class XII, Part I, 2018 Edition, pp 110-111; ISBN 81-7450-648-9.
[21]	M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P.Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O¨ . Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision E.01 2009 (Gaussian, Inc., Wallingford, C
[22]	Peter Atkins & Julio De Paula. Elements of Physical Chemistry. International Edition, Oxford University Press 2017, pp 262-263.