<< Chapter < Page Chapter >> Page >

In this lab we will be studying the reaction of cyclopentadiene with maleic anhydride. From previous knowledge of Diels Alder reactions you should be able to predict the stereochemistry of the products. Cyclic dienes can give stereoisomeric products depending on whether the dienophile lies under or away from the diene in the transition state. The endo product is usually the major product (due to kinetic control).

In Figure 12, the diene and dienophile are aligned directly over each other which yields the endo product(dienophile under or in = endo).In Figure 13, the diene and dienophile are staggered with respect with to each other which yields the exo product(dienophile exposed or out = exo).

Pre-Lab 1: Diels-Alder and Melting Point (Total 10 points)

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. Usually, you will not be allowed to begin the lab until you have completed this assignment–allowance made for the first week.

1. The reaction, as you will notice, occurs very rapidly. State two characteristics of the starting materials that make them ideal coupling partners for this reaction (i.e. what are good characteristics for reactants in Diels Alder reactions). (2 points)

2. Write the major product of the following reactions, if there is no product specify why. (4 points)

3. a) Which of these dienes gives the FASTEST reaction with maleic anhydride, why? (2 points)

(b) Which of these dienophiles gives the FASTEST reaction with cyclopentadiene and why? (2 points)


You will be assessed on:

  • Pre-Lab assignment completed prior to lab, TA will check
  • Melting points of urea, trans-cinnamic acid, of their mixture in different ratios and of the Diels-Alder reaction product
  • Graph of melting point versus composition of the mixture urea/trans-cinnamic acid
  • Your explanation as to why your measured melting point ranges do not match those in literature
  • IR spectrum of product
  • Write-up in your Lab Notebook
  • Answers to post-lab questions
  • TA evaluation of lab procedure.Material Required

Equipment Chemicals

  • Capillary tube Cinnamic acid, urea
  • Test tubes Diphenyl acetic acid
  • Round bottom flask (5 mL) Dicyclopentadiene
  • Beaker Maleic anhydride, Ethyl acetate
  • Glass rod (for recrystalisation) Petroleum ether
  • Filter paper


Wear gloves all the time, especially when you are working with NaOH, HCl. Keep safety glasses on all the time.

Experimental procedure for melting point

Part i. the effect of purity on melting point

In this section you will take two compounds (cinnamic acid and urea) and create mixtures of them to determine what effect this will produce, as well as the extent of this effect depending on the composition of the sample.

1.Prepare a capillary tube containing urea as well as one containing cinnamic acid. Take the melting point of each and compare it to the "Houston" values (which your TA will have). Repeat if the values are not correct.

Questions & Answers

what is the stm
Brian Reply
is there industrial application of fullrenes. What is the method to prepare fullrene on large scale.?
industrial application...? mmm I think on the medical side as drug carrier, but you should go deeper on your research, I may be wrong
How we are making nano material?
what is a peer
What is meant by 'nano scale'?
What is STMs full form?
scanning tunneling microscope
how nano science is used for hydrophobicity
Do u think that Graphene and Fullrene fiber can be used to make Air Plane body structure the lightest and strongest. Rafiq
what is differents between GO and RGO?
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
what is Nano technology ?
Bob Reply
write examples of Nano molecule?
The nanotechnology is as new science, to scale nanometric
nanotechnology is the study, desing, synthesis, manipulation and application of materials and functional systems through control of matter at nanoscale
Is there any normative that regulates the use of silver nanoparticles?
Damian Reply
what king of growth are you checking .?
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
yes I'm doing my masters in nanotechnology, we are being studying all these domains as well..
what school?
biomolecules are e building blocks of every organics and inorganic materials.
anyone know any internet site where one can find nanotechnology papers?
Damian Reply
sciencedirect big data base
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.
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
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
characteristics of micro business
for teaching engĺish at school how nano technology help us
How can I make nanorobot?
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
how can I make nanorobot?
what is fullerene does it is used to make bukky balls
Devang Reply
are you nano engineer ?
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.
what is the actual application of fullerenes nowadays?
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.
how did you get the value of 2000N.What calculations are needed to arrive at it
Smarajit Reply
Privacy Information Security Software Version 1.1a
Got questions? Join the online conversation and get instant answers!
Jobilize.com Reply

Get the best Algebra and trigonometry course in your pocket!

Source:  OpenStax, Chem217labsfall07. OpenStax CNX. Oct 16, 2007 Download for free at http://cnx.org/content/col10463/1.4
Google Play and the Google Play logo are trademarks of Google Inc.

Notification Switch

Would you like to follow the 'Chem217labsfall07' conversation and receive update notifications?