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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)

Grading

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

SAFETY

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

where we get a research paper on Nano chemistry....?
Maira Reply
nanopartical of organic/inorganic / physical chemistry , pdf / thesis / review
Ali
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
hey
Giriraj
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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