TCE
    
|
The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 18
(2013) pp 096-098
DOI 10.1007/s00897132480a
Solvent-Free Pyridine-Free Peracetylation of Glucose: An Organic Chemistry Experiment
Li Cai*,†, Christopher Rufty‡
†Division of Mathematics and Science, University of South Carolina Salkehatchie, 807 Hampton Street, Walterboro, SC 29488, caili@mailbox.sc.edu; ‡Department of Chemical Engineering, University of South Carolina, 301 Main Street, Columbia, SC 29208
Received February 19, 2013. Accepted March 16, 2013.
Published: 3 May 2013
Abstract. An easy, safe, low-cost, high-yield, and environmentally friendly acetylation reaction promoted by molecular sieves was introduced as an organic chemistry experiment. This experiment emphasizes topics of ester bond formation, addition-elimination mechanism, carbohydrates, and protection groups present in the undergraduate organic chemistry curriculum. The exercise may be completed in a single laboratory period and covers the most commonly used laboratory techniques in organic chemistry, such as reaction work-up, TLC and staining, product purification and isolation. The resulting product can be used for further experiments; for instance, the synthesis of glycosyl halide and glycosyl azide.
Key Words: Laboratories and Demonstrations; organic chemistry; carbohydrates; acetylation; thin layer chromatography
(*) Corresponding author. (E-mail: caili@mailbox.sc.edu)
Article in PDF format (99 KB) HTML format
© The Chemical Educator 1996-2015