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Has Anybody Done This Lab

Page history last edited by jbfriesen 9 years, 1 month ago

This page is dedicated to discussion of laboratory experiments that the OChemOnline community finds particularly instructive and interesting.

 

The OChemOnline community is especially interested in hearing about experiments that have been recently published in Journal of Chemical Education.

 

We do not intend to reproduce published work.

If a lab handout is extensively copied from a published source, please reference the source instead of posting the laboratory handout. Another option may be to delete those sections which are copied from published sources from the lab handout before posting.

Fall Semester Labs:

At Dominican University we do a four-week first semester introductory sequence.

All four labs together lead to the separation and identification of a mixture of two unknowns.

Lab #1 Thin Layer Chromatography

Lab #2 Liquid/Liquid Extraction 

Lab #3 Recrystallization

Lab #4 Melting Point Determination

2010 Labs from Dominican University

Caffeine from Tea

Caffeine from Beverages

Exploring Stereochemistry with Molecular Models

Diels Alder

Dehydration of Methylcyclohexanols

Kinetic Investigation of Substitution

Steam Distillation of Essential Oils

2008 Labs from Dominican University

Chromatography Theory Worksheet

2007 Labs from Dominican University

Williamson Ether Synthesis

The Didehydrobromination of 1,2-dibromo-1,2-diphenylethane

Post an experiment and/or discussion! invite key = ochemrules

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Spring Semester 2011:

ONS Solubility Challenge

This is our second year to participate in this interesting collaboration.

Exploring Biphasic Solvent Systems

This lab uses Reichardt's Dye, which has some amazing properties. This experiment is related to Dr. Friesen's research.

Oxidation of Secondary Alcohols to Ketones with Household Bleach (NaOCl).

We studied the influence of reaction time and rate of bleach addition.

Combinatorial Synthesis of Azo Dyes

We introduced a new nucleophilic aromatic compound, 1-nitroso-2-naphthol, to the combinatorial scheme.

Synthesis of a Tertiary Alcohol Using a Pre-Made Grignard Reagent

We compared three different ether solvents: ethyl ether, methyl t-butylether, and tetrahydrofuran.

Synthesis of Aromatic Esters

A combinatorial synthetic scheme with carboxylic acids 4-methylbenzoic acid, 4-methoxybenzoic acid, 2-methoxybenzoic acid and alcohols 1-propanol and 2-propanol.

Synthesis of Chemiluminescent Esters

A combinatorial synthesis of "glow stick" esters.

Three Step Synthesis (Final) Project

 

Spring Semester 2009:

Our first experiment of the semester was our attempt to contribute to the Open Notebook Science "Solubility Challenge." Determining the solubility of an organic compound in an organic solvent is not an awfully advanced experiment, but the education value of the endeaver was enhanced by having student design their own procedure based on the ONS solubility challenge guidelines. Some student results were contributed to the ONS Solubility Challenge wiki.

Diels Alder Reaction between Anthracene and Maleic Anhydride. This is a classic Organic Chemistry reaction. Many references to this procedure can be found on the internet, We were adapting the basic procedure from "Experiments in Organic Chemistry" 2nd edition (2000) by R.K. Hill & J. Barbaro.

 Steam Distillation of Essential Oil  We distilled cloves, anise, oregano, fennel, and cumin to collect and analyse the extracted essential oils.

This is a very basic experiment that is found in several Sophomore Organic Chemistry Laboratory Manuals.

"Combinatorial Synthesis of Azo Dyes" lab that we had done last Spring.

This year we tried a new electrophilic naphthalene derivative (1,5-dihydroxynaphthalene) to react with the azo compounds.

"Oxidation of Secondary Alcohols to Ketones with Household Bleach (NaOCl)."

We had done a variation of this experiment with isoborneol in previous years.

This year we studied the oxidation of 2, 3, and 4-methyl-1-cyclohexanols.

An additional week was added to the oxidation experiment where we tried to improve the previous week's experiment or evaluate and alternative way to oxidize alcohols such as the "Solvent-free Oxidation of Secondary Alcohols to Ketones with Potassium Permanganate/Copper Sulfate"

Synthesis of a Tertiary Alcohol Using a Pre-Made Grignard Reagent, but this year we used 2, 3, and 4-methyl-1-cyclohexanone instead of benzophenone.

It was very interesting to compare the relative ratios of the two diastereomeric products formed (cis and trans-methyl-1-phenyl-1-cyclohexanol).

Ethanol from Various Starch Sources.The main sources were frozen sweet corn, frozen potatoes, and minute rice.

Synthesis of Aromatic Esters. We synthesized two esters from last year: propyl 2-methylbenzoate, and propyl 4-methylbenzoate. We also made four newe esters: isopropyl 2-methylbenzoate, isopropyl 4-methylbenzoate, propyl gallate, and isopropyl gallate.

We ended the semester with the Synthesis of Luminol, an experiment adapted from Experiment 48: Luminol, in Pavia, Lampman and Kriz, “Introduction to Organic Laboratory Techniques: A Contemporary Approach” (1976) Saunders.

 

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Spring Semester 2008:

 #1 Our first "regular" experiment of the Spring 2008 Semester was "Steam Distillation of Essential Oils

We distilled cloves, anise, caraway, cinnamon, and cumin to collect and analyse the extracted essential oils.

This is a very basic experiment that is found in several Sophomore Organic Chemistry Laboratory Manuals.

#2a "Oxidation of Cinnamyl Alcohol using Pyridinium Chlorochromate" was developed by a group of four students from: Experiment #14 in Mohrig, J. R. “Modern projects and experiments in organic chemistry: Miniscale and standard taper microscale.” (2003) New York; Basingstoke: W.H. Freeman; Palgrave Macmillan.

#2b "Synthesis of a Tertiary Alcohol Using a Pre-Made Grignard Reagent" was adapted by a group of four students from a recent JCE article: Michael A. G. Berg and Roy D. Pointer. J. Chem. Educ. 2007, 84, 483.

#3 "Identification of a Conjugated Diene from Eucalyptus Oil” was adapted by a group of 4 students from: Lehman, J. W., Lehman, J. W., Operational organic chemistry, & 3rd. (2004). Microscale operational organic chemistry : A problem-solving approach to the laboratory course. Upper Saddle River, N.J: Pearson Prentice Hall. This was an interesting find, I thought. I have done a couple of different Diels Alder experiments over the years: maleic anhydride and cyclopentadiene, as well as maleic anhydride and anthracene.

#4 “Synthesis and Recrystallization of Adipic Acid” was adapted by a group of 4 students from: Experiment 5, Doxsee, K. M., & Hutchison, J. E. (2004). Green organic chemistry : Strategies, tools, and laboratory experiments Southbank, Vic., Australia ; United States: Thomson-Brooks/Cole

#5 "Combinatorial Synthesis of Azo Dyes" was adapted from: A Combinatorial Experiment Suitable for Undergraduate Laboratories Benjamin W. Gung and Richard T. Taylor in the Journal of Chemical Education, Vol 81, No. 11, November 2004 and Daniel R. Palleros,Experimental Organic Chemistry, John Wiley & Sons, Inc., 2000, pp. 627-628.

Its a variation of the classic "Synthesis of Methyl Orange" that I performed as an undergraduate.

#6 Synthesis of Isopentyl Acetate (Banana Oil) was developed by a team of students from a website: “Preparation of Banana Oil” . Many websites and lab manuals have versions of this very same experiment. I performed this experiment in 1979 from Pavia D. L.; Lampman G. M.; Kriz G. S. “Introduction to Organic Laboratory Techniques: a contemporary approach” 1st edition 1976 W. B. Saunders Company.

#7 “Synthesis of Chemiluminescent Esters” was developed by a team of students from a recent JCE article: “Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students,” Duarte, Robert; Nielsen, Janne T.; Dragojlovic, Veljko. J. Chem. Educ. 2004, 81, 1010. A good resource for this experiment is a website: “Chemiluminescence of Oxalate Esters” 

#9 “Vanillin Synthesis from 4-Hydroxybenzaldehyde” This lab was developed by a team of students from a recent JCE article: Vanillin Synthesis from 4-Hydroxybenzaldehyde.” Douglass F. Taber, Shweta Patel, Travis M. Hambleton, and Emma E. Winkel, J. Chem. Educ. 2007, 84, 1158. An online version of the lab was available at the Douglass Taber website; University of Delaware.

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Introduction to Organic Chemistry Labs: Spring 2010

Physical Characteristics of Organic Compounds-

Phytochemical Antioxidants with Potential Benefits in Foods: Part I.

Phytochemical Antioxidants with Potential Benefits in Foods: Part II.

Scientific Exploration of the Mentos & Diet Coke “Geyser”.

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We are looking for schools to join us in a collaborative project studying the:

#10 Synthesis of Aromatic Esters"This lab was developed from a recent JCE article: Wade P.A.; Rutkowsky S.A.; King D.B. A simple combinatorial experiment based on Fischer esterification - An experiment suitable for the first-semester organic chemistry lab. J Chemical Education 2006, 83(6), 927-928. This, of course, is a version of the ever-popular “banana-oil” lab found in a multitude of laboratory manuals such as: Pavia D. L.; Lampman G. M.; Kriz G. S. “Introduction to Organic Laboratory Techniques: a contemporary approach” 1st edition 1976 W. B. Saunders Company.

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