CHEM 2081 Esterification Lab Report PDF

Preview

Summary

Esterification Lab Report...

Description

Experiment 6: Esterification Hieu Pham TA: Safaa Sader November 23rd, 2020

Introduction: Esterification is the process that makes the ester as product and the chemical reaction between a carboxylic acid and an alcohol with the present of an acid catalyst, which is Dowex 50x2-100 ion exchange resin in this experiment. It normally proceeds the reactions in five steps. In step 1, the protonation of the carbonyl oxygen by the carboxylic acid makes the carbonyl carbon a better electrophile. Then it undergoes the 1,2 addition by the alcohol in step 2 and the proton from alcohol is transferred to one of the OH groups in step 3. In step 4, the subsequence of 1,2elimination of water causes the ester to protonate and in the last step (step 5), the ester is deprotonated.

Conclusion: In this experiment, the unknown alcohol (13A) was reacted with glacial acetic acid and Dowex 50x2-100 ion exchange resin. The experiment proceeded as expected with some very small error or mistakes. The layers were separated well and the amount of sample was collected as much as expected. After being dried out, the highest boiling point of the sample was also recorded at 80°C and it smelled like blueberry so I can conclude that the product ester was t-butyl acetate which has the boiling point of 98°C and therefore the percentage error was calculated to be 18.4% and starting compounds of acetic acid and t-butanol. There was a small gap between the two temperatures can be explained because of the sample was not completely dry or the mistake made when collecting product or there was a little bit too much of the reactants.

Calculation: % error = [(80 – 98)/98] *100% = 18.4%

Reaction Mechanisms:

References: 1. Morvant, Mark C, et al. CHEM 2081 Organic Chemistry II Laboratory Manual. HaydenMcNeil, LLC, 2020, pp 31-33. 2. Master Organic Chemistry, “Conversion of carboxylic acids to esters using acid and alcohols (Fischer Esterification)”, https://www.masterorganicchemistry.com/reaction-guide/conversionof-carboxylic-acids-to-esters-using-acid-and-alcohols-fischeresterification/?fbclid=IwAR2Nr_OKCf2gFr7kpjH5skJErqL5T6s0zhslHJttAb4EYHeK9UPflwLjPQ, Accessed on 11/23/2020...