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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


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)


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.


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


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

Introduction about quantum dots in nanotechnology
Praveena Reply
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s. Reply
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Devang Reply
are you nano engineer ?
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Abhijith Reply
Mostly, they use nano carbon for electronics and for materials to be strengthened.
is Bucky paper clear?
carbon nanotubes has various application in fuel cells membrane, current research on cancer drug,and in electronics MEMS and NEMS etc
so some one know about replacing silicon atom with phosphorous in semiconductors device?
s. Reply
Yeah, it is a pain to say the least. You basically have to heat the substarte up to around 1000 degrees celcius then pass phosphene gas over top of it, which is explosive and toxic by the way, under very low pressure.
Do you know which machine is used to that process?
how to fabricate graphene ink ?
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s. Reply
of graphene you mean?
or in general
in general
Graphene has a hexagonal structure
On having this app for quite a bit time, Haven't realised there's a chat room in it.
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Sanket Reply
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Damian Reply
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abeetha Reply
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