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A Guided Inquiry Laboratory Activity to Explore Reactivity of Carbonyl Compounds

A Guided Inquiry Laboratory Activity to Explore Reactivity of Carbonyl Compounds
Contributors
mtracey
Associate Professor of Chemistry | University of Pittsburgh, Johnstown
Manisha Nigam
Professor | University of Pittsburgh, Johnstown
Two white solid starting materials combine to make a colored product in the absence of solvent.
Summary
A laboratory activity to demonstrate reactivity of carbonyl compounds using Meldrum's acid as a nucleophile is presented. The experiment requires no solvent and can be completed in a single 3-4 hour laboratory period. Substrate information and related spectroscopic information are provided.


Tracey, M. P., Nigam, M., Pirzada, E., & Osman, T. (2024). A solventless carbonyl addition reaction as a guided inquiry laboratory activity for second-year undergraduate organic students. Green Chemistry Letters and Reviews, 17(1). https://doi.org/10.1080/17518253.2024.2400121
Keywords
Green organic chemistry
Experiment
NMR
Condensation Chemistry
Guided-Inquiry Instruction

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Moderation state
Published
Object Type
Laboratory experiment
Audience
Introductory Undergraduate
Published on
Green Chemistry Principles
Atom Economy
Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Reduce Derivatives
U.N. Sustainable Development Goals (SDGs)
Quality Education
Learning Goals/Student Objectives
Study the reactivity of carbonyl compounds
Determine the mechanism for an unknown reaction (Knoevenagel condensation)
Characterize a product by NMR spectroscopy
Predict reactivity of various species based on structure
Common pedagogies covered
Hands-on learning
Problem-based learning
Student-centered learning
Time required (if applicable)
3 - 4 hours

Submitted by

mtracey
Safety Precautions, Hazards, and Risk Assessment
Meldrum's acid, p-anisaldehyde, p-tolualdehyde, veratraldehyde, p-nitrobenzaldehyde, N,N-dimethylaminobenzaldehyde, p-hydroxybenzaldehyde are irritants.

Ethanol is flammable.
Teacher Recommendations or Piloting Data (if available)
It is recommended to broadly inform students about addition reactions via carbonyl compounds, but not to fully explain the aldol/Knoevenagel condensations. If IR data is collected, the presence of residual water/ethanol may skew student interpretation for the reaction pathway (seeing an OH peak and concluding it's an addition product).
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A solventless carbonyl addition reaction as a guided inquiry laboratory activit…
Creative Commons License
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.