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  • Reaction of an aromatic compound with an acyl halide and a Lewis Acid
  • The electrophile is an acylium ion.
  • The para product generally predominates in the acylation of substituted rings.

- Unlike the Friedel-Crafts alkylation, the acylation reaction does not suffer from

rearrangement of the electrophile nor is the product susceptible to further reaction.

- The Freidel Crafts acylation reaction can be used to synthesize alkyl benzenes

indirectly.

Aromaticity of organic compounds:

Although many aromatic compounds are based on the prototypical benzene ring system, many other aromatic compounds are known. In general, aromaticity results from a cyclic, planar, fully-conjugated array of atoms with a total of 4n+2 (n = integer) π electrons. Thus neutral compounds such as pyrrole and furan, as well as charged species such as tropylium, cyclopentadienyl and cyclopropenium ions, all represent aromatic compounds.

In this experiment, rather than using a simple benzene derivative as a reactant, you will explore the Friedel-Crafts acylation of a cyclopentadienyl ring contained in an organometallic compound (i.e. a compound containing one or more bonds between carbon and a transition metal). The substrate, ferrocene, contains two cyclopentadienyl rings which form a "sandwich" with the central iron atom. Although the presence of the metal atom confers some unusual properties on ferrocene, the cyclopentadienyl rings undergo many reactions typical of aromatic compounds. In particular, ferrocene efficiently undergoes Friedel-Crafts acylation and this is the reaction you will investigate.

Friedel-Crafts acylation of ferrocene

Pre-lab 4: friedel-crafts reaction

(Total 10 points)

Click here for the Pre-Lab

Name(Print then sign): ___________________________________________________

Lab Day: ___________________Section: ________TA__________________________

This assignment must be completed individually and turned in to your TA at the beginning of lab. You will not be allowed to begin the lab until you have completed this assignment.

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

Support your answer. (3 points)

2. Show the mechanism for the following reaction. Be sure to include all intermediates. (5 points)

3. predict the products from the following reactions. (2 points)

Grading

You will be assessed on:

  • Completion of pre lab questions.
  • Write-up in your lab notebook
  • Completion of report questions.
  • TA evaluation of lab procedure.

Materials

Equipment chemicals

  • Water bath Ferrocene
  • Stir bar Acetic anhydride
  • Round bottom flask (10mL) 85% phosphoric acid
  • Hirsch funnel 3 M aq NaOH
  • Beakers (50, 400 mL) NaHCO 3 size 12{ ital "NaHCO" rSub { size 8{3} } } {}
  • TLC plates Hexanes
  • Filter paper Toluene, absolute EtOH

Safety

Phosphoric acid and acetic anhydride are corrosive and acetic anhydride is also a lachrymator. Avoid contact or undue exposure to vapor. Wear gloves all the time, especially when you are working with corrosive reagents. Keep safety glasses on all the time. Dispose of organic substances in their proper containers.

Questions & Answers

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
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
anyone know any internet site where one can find nanotechnology papers?
Damian Reply
research.net
kanaga
sciencedirect big data base
Ernesto
Introduction about quantum dots in nanotechnology
Praveena Reply
what does nano mean?
Anassong Reply
nano basically means 10^(-9). nanometer is a unit to measure length.
Bharti
do you think it's worthwhile in the long term to study the effects and possibilities of nanotechnology on viral treatment?
Damian Reply
absolutely yes
Daniel
how to know photocatalytic properties of tio2 nanoparticles...what to do now
Akash Reply
it is a goid question and i want to know the answer as well
Maciej
characteristics of micro business
Abigail
for teaching engĺish at school how nano technology help us
Anassong
How can I make nanorobot?
Lily
Do somebody tell me a best nano engineering book for beginners?
s. Reply
there is no specific books for beginners but there is book called principle of nanotechnology
NANO
how can I make nanorobot?
Lily
what is fullerene does it is used to make bukky balls
Devang Reply
are you nano engineer ?
s.
fullerene is a bucky ball aka Carbon 60 molecule. It was name by the architect Fuller. He design the geodesic dome. it resembles a soccer ball.
Tarell
what is the actual application of fullerenes nowadays?
Damian
That is a great question Damian. best way to answer that question is to Google it. there are hundreds of applications for buck minister fullerenes, from medical to aerospace. you can also find plenty of research papers that will give you great detail on the potential applications of fullerenes.
Tarell
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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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