Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that enhances student understanding of nmr spectroscopy

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

This laboratory experiment was developed to provide two safe and effective ways to instruct undergraduate organic chemistry students about the catalytic palladium hydrogenation reaction. Students hydrogenate curcumin either by refluxing it as a suspension in methanol with 10% Pd/C and a transfer hydrogenation chemical, such as cyclohexene, or by using a hydrogenation flow reactor, an H-Cube, a type of instrument that is rapidly becoming an industry standard. Students develop chromatography and spectroscopy skills by performing thin-layer chromatographic analysis, and if necessary, running a silica gel column on the crude material, followed by acquiring a proton NMR spectrum of the product. Approximately 101 undergraduate students performed this experiment, and the experiment's effectiveness was assessed by two methods: a qualitative postlab student self-assessment and identical quantitative pre-and postlab tests. The tests indicated that the students showed significant improvement in their understanding of NMR spectroscopy after performing the experiment.

Original languageEnglish (US)
Pages (from-to)930-933
Number of pages4
JournalJournal of Chemical Education
Volume90
Issue number7
DOIs
StatePublished - Jul 9 2013

Fingerprint

Curcumin
Biological Products
Hydrogenation
Spectroscopy
Students
experiment
student
Experiments
Thin layer chromatography
Silica Gel
Palladium
laboratory experiment
self-assessment
Chromatography
Nuclear magnetic resonance spectroscopy
Methanol
tetrahydrocurcumin
Protons
Suspensions
chemistry

Keywords

  • Alkenes
  • Hands-On Learning/Manipulatives
  • Laboratory Instruction
  • Natural Products
  • NMR
  • Organic Chemistry
  • Oxidation/Reduction
  • Second-Year Undergraduate/General
  • Thin Layer Chromatography
  • UV-Vis Spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)
  • Education

Cite this

@article{3b8fc68392594a008e6a1705a80d686c,
title = "Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that enhances student understanding of nmr spectroscopy",
abstract = "This laboratory experiment was developed to provide two safe and effective ways to instruct undergraduate organic chemistry students about the catalytic palladium hydrogenation reaction. Students hydrogenate curcumin either by refluxing it as a suspension in methanol with 10{\%} Pd/C and a transfer hydrogenation chemical, such as cyclohexene, or by using a hydrogenation flow reactor, an H-Cube, a type of instrument that is rapidly becoming an industry standard. Students develop chromatography and spectroscopy skills by performing thin-layer chromatographic analysis, and if necessary, running a silica gel column on the crude material, followed by acquiring a proton NMR spectrum of the product. Approximately 101 undergraduate students performed this experiment, and the experiment's effectiveness was assessed by two methods: a qualitative postlab student self-assessment and identical quantitative pre-and postlab tests. The tests indicated that the students showed significant improvement in their understanding of NMR spectroscopy after performing the experiment.",
keywords = "Alkenes, Hands-On Learning/Manipulatives, Laboratory Instruction, Natural Products, NMR, Organic Chemistry, Oxidation/Reduction, Second-Year Undergraduate/General, Thin Layer Chromatography, UV-Vis Spectroscopy",
author = "Carl Wagner and Pamela Marshall and Thomas Cahill and Zeynab Mohamed",
year = "2013",
month = "7",
day = "9",
doi = "10.1021/ed3002489",
language = "English (US)",
volume = "90",
pages = "930--933",
journal = "Journal of Chemical Education",
issn = "0021-9584",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that enhances student understanding of nmr spectroscopy

AU - Wagner, Carl

AU - Marshall, Pamela

AU - Cahill, Thomas

AU - Mohamed, Zeynab

PY - 2013/7/9

Y1 - 2013/7/9

N2 - This laboratory experiment was developed to provide two safe and effective ways to instruct undergraduate organic chemistry students about the catalytic palladium hydrogenation reaction. Students hydrogenate curcumin either by refluxing it as a suspension in methanol with 10% Pd/C and a transfer hydrogenation chemical, such as cyclohexene, or by using a hydrogenation flow reactor, an H-Cube, a type of instrument that is rapidly becoming an industry standard. Students develop chromatography and spectroscopy skills by performing thin-layer chromatographic analysis, and if necessary, running a silica gel column on the crude material, followed by acquiring a proton NMR spectrum of the product. Approximately 101 undergraduate students performed this experiment, and the experiment's effectiveness was assessed by two methods: a qualitative postlab student self-assessment and identical quantitative pre-and postlab tests. The tests indicated that the students showed significant improvement in their understanding of NMR spectroscopy after performing the experiment.

AB - This laboratory experiment was developed to provide two safe and effective ways to instruct undergraduate organic chemistry students about the catalytic palladium hydrogenation reaction. Students hydrogenate curcumin either by refluxing it as a suspension in methanol with 10% Pd/C and a transfer hydrogenation chemical, such as cyclohexene, or by using a hydrogenation flow reactor, an H-Cube, a type of instrument that is rapidly becoming an industry standard. Students develop chromatography and spectroscopy skills by performing thin-layer chromatographic analysis, and if necessary, running a silica gel column on the crude material, followed by acquiring a proton NMR spectrum of the product. Approximately 101 undergraduate students performed this experiment, and the experiment's effectiveness was assessed by two methods: a qualitative postlab student self-assessment and identical quantitative pre-and postlab tests. The tests indicated that the students showed significant improvement in their understanding of NMR spectroscopy after performing the experiment.

KW - Alkenes

KW - Hands-On Learning/Manipulatives

KW - Laboratory Instruction

KW - Natural Products

KW - NMR

KW - Organic Chemistry

KW - Oxidation/Reduction

KW - Second-Year Undergraduate/General

KW - Thin Layer Chromatography

KW - UV-Vis Spectroscopy

UR - http://www.scopus.com/inward/record.url?scp=84880008681&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880008681&partnerID=8YFLogxK

U2 - 10.1021/ed3002489

DO - 10.1021/ed3002489

M3 - Article

AN - SCOPUS:84880008681

VL - 90

SP - 930

EP - 933

JO - Journal of Chemical Education

JF - Journal of Chemical Education

SN - 0021-9584

IS - 7

ER -