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Experimental procedure

1. Place 0.25 g. of ferrocene in a 10 mL round-bottom flask containing a magnetic stir bar. Prepare a hot water bath by heating the water to nearly the boiling point while preparing the following reaction mixture.

2. In a fume hood, add 1.0 mL of acetic anhydride and 0.15 mL of 85% phosphoric acid to the flask. The reaction mixture should heat up and darken in color. Swirl the flask, heating occasionally in a hot water bath if necessary, until all the ferrocene dissolves.

3. Attach a reflux condenser then heat the reaction mixture with stirring in the hot water bath prepared in step 1. Heat the mixture for 10 minutes during which time a purple color may develop.

Workup and purification:

4. Pour the reaction mixture onto 2 or 3 cubes of ice in a 400 mL beaker, then rinse the flask with two 5 mL portions of ice water. (A black residue may remain in the flask.) Stir the orange-brown mixture with a glass rod for a few minutes. Any insoluble black material present will be removed in the following steps.

5. Add 6.0 mL of 3 M aqueous NaOH solution, then carefully add solid sodium bicarbonate in small portions until the remaining acid has been neutralized (about 2-3 grams). Use great care to avoid excessive foaming during bicarbonate addition. This step can be done with magnetic stirring, but make sure to use a stirring plate that is not hot. Stir well and crush any lumps to afford a dark-brown suspension.

6. Allow the mixture to stand for 20 minutes, and then collect the crude product by vacuum filtration. Continue to pull air through the product for a few minutes to dry it. Finish the drying process by pressing the solid product between two sheets of filter paper or paper towels. Save some of this crude product for TLC analysis.

7. Transfer the solid and a stir bar to a 50 mL beaker and add 10 mL of hexanes. Boil for 5 minutes with stirring, and then decant the dark-orange solution into another Erlenmeyer flask leaving behind a black gummy substance. If you boil off all the liquid, try again with another 10 mL of hexane and lower heat.

8. To the hot solution, add a spatula-full of decolorizing carbon (If you use too much, you will reduce your yield of carbon). Heat with swirling, and then perform a hot filtration to remove the decolorizing carbon.

9. Set the flask aside to cool slowly. Red-brown needles of acetylferrocene should begin to form. Once the flask has reached room temperature, cool it in ice. Collect the crystalline product by vacuum filtration and washing with a small quantity of cold hexane, then dry by continuing to pull air through the product for a few minutes. If you add to much cold hexane here, you will lose your product.

Characterization:

10. Record the yield and melting point range for your recrystallized acetylferrocene.

11. Analyze your crude and recrystallized products by TLC. Separately dissolve very small amounts of pure ferrocene, the crude product, and the recrystallized acetylferrocene in a few drops of toluene. Spot the solutions on silica gel plates and develop with 30:1 toluene/absolute ethanol. Visualization is simple as each compound is brightly colored.

Safety

Wear safety goggles and gloves all the time.

Waste disposal

Organic compounds must be disposed in the proper container.

Approximate lab time 2 – 2 ½ hours

Report 4: friedel- crafts

(Total 30 points)

(Click here for the Report Form

Note: In preparing this report you are free to use references and consult with others. However, you may not copy from other students’ work or misrepresent your own data (see honor code).

Name(Print then sign): ___________________________________________________

Lab Day: ___________________Section: ________TA__________________________

1. Draw the mechanism for the reaction of ferrocene, acetic anhydride, and phosphoric acid. (6 points)

2. Show your theoretical and percent yield calculations for the reaction. (3 points)

 

 

3. The melting point of your re-crystallized acetylferrocene is: ---- (2 points)

4. Draw the TLC plates and show your R f size 12{R rSub { size 8{f} } } {} calculations (4 points)

5. Classify each of the following species as anti-aromatic, aromatic, or nonaromatic.

Support your answer. (4 points)

6. Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high (40

kcal/mol), but the compound below was observed to have a rotational barrier of only about 20 kcal/mol. Explain this result. (3 points)

7. Propose a mechanism for the following reaction. (8 points)

Questions & Answers

where we get a research paper on Nano chemistry....?
Maira Reply
what are the products of Nano chemistry?
Maira Reply
There are lots of products of nano chemistry... Like nano coatings.....carbon fiber.. And lots of others..
learn
Even nanotechnology is pretty much all about chemistry... Its the chemistry on quantum or atomic level
learn
Google
da
no nanotechnology is also a part of physics and maths it requires angle formulas and some pressure regarding concepts
Bhagvanji
Preparation and Applications of Nanomaterial for Drug Delivery
Hafiz Reply
revolt
da
Application of nanotechnology in medicine
what is variations in raman spectra for nanomaterials
Jyoti Reply
I only see partial conversation and what's the question here!
Crow Reply
what about nanotechnology for water purification
RAW Reply
please someone correct me if I'm wrong but I think one can use nanoparticles, specially silver nanoparticles for water treatment.
Damian
yes that's correct
Professor
I think
Professor
Nasa has use it in the 60's, copper as water purification in the moon travel.
Alexandre
nanocopper obvius
Alexandre
what is the stm
Brian Reply
is there industrial application of fullrenes. What is the method to prepare fullrene on large scale.?
Rafiq
industrial application...? mmm I think on the medical side as drug carrier, but you should go deeper on your research, I may be wrong
Damian
How we are making nano material?
LITNING Reply
what is a peer
LITNING Reply
What is meant by 'nano scale'?
LITNING Reply
What is STMs full form?
LITNING
scanning tunneling microscope
Sahil
how nano science is used for hydrophobicity
Santosh
Do u think that Graphene and Fullrene fiber can be used to make Air Plane body structure the lightest and strongest. Rafiq
Rafiq
what is differents between GO and RGO?
Mahi
what is simplest way to understand the applications of nano robots used to detect the cancer affected cell of human body.? How this robot is carried to required site of body cell.? what will be the carrier material and how can be detected that correct delivery of drug is done Rafiq
Rafiq
if virus is killing to make ARTIFICIAL DNA OF GRAPHENE FOR KILLED THE VIRUS .THIS IS OUR ASSUMPTION
Anam
analytical skills graphene is prepared to kill any type viruses .
Anam
Any one who tell me about Preparation and application of Nanomaterial for drug Delivery
Hafiz
what is Nano technology ?
Bob Reply
write examples of Nano molecule?
Bob
The nanotechnology is as new science, to scale nanometric
brayan
nanotechnology is the study, desing, synthesis, manipulation and application of materials and functional systems through control of matter at nanoscale
Damian
Is there any normative that regulates the use of silver nanoparticles?
Damian Reply
what king of growth are you checking .?
Renato
What fields keep nano created devices from performing or assimulating ? Magnetic fields ? Are do they assimilate ?
Stoney Reply
why we need to study biomolecules, molecular biology in nanotechnology?
Adin Reply
?
Kyle
yes I'm doing my masters in nanotechnology, we are being studying all these domains as well..
Adin
why?
Adin
what school?
Kyle
biomolecules are e building blocks of every organics and inorganic materials.
Joe
how did you get the value of 2000N.What calculations are needed to arrive at it
Smarajit Reply
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Source:  OpenStax, Chem217labsfall07. OpenStax CNX. Oct 16, 2007 Download for free at http://cnx.org/content/col10463/1.4
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