Solvent-Free Diels-Alder Reaction

150 pt Laboratory Report Summer 2015

Below are guidelines only. You are responsible for the sum total of your data collected, well organized
presentation, and proper interpretation. Dont forget the additional questions at the end.
Title, Name, TA Name, Section, Date.
10 pts Quality of Writing (scientific writing, spelling, grammar, sentence structure, *citations)
10 pts Purpose and Reaction Scheme Draw all three products expected (1A, 1B, 2) enantiomers not required.
10 pts Mechanism: Draw the mechanism involved in the formation of 1A or 1B and compound 2. Be sure each
arrow is properly drawn.
10 pts Procedure: Reference the procedure followed and state any significant deviations or experimental details
that would impact the outcome of the experiment.
5 pts

Reagents Table - as usual

55 pts Results and Observations: Use table format where appropriate. Include all observations for the reaction
and recrystallization(s). Present mass of crude product, recrystallized, and all appropriate yields (predict
theoretical yield for products 1 and 2) and calculations. Present the melting point data and any
observations noted. Literature melting points are given below.1 Present TLC data with Rf values. Present
all IR data and attach spectrum. Attach the 1H NMR and present data including J values for all peaks
between 2 5 ppm. No J values needed for aromatic region. Attach the X-ray structure data given in lab
and include the conclusion you made from the structure in the conclusions and discussion of the report.
More detailed questions will be asked in the Additional Questions section:
. Literature Mpt1
182-183 oC (1A, endo)
194-194.5 oC (1B, exo)
Reference: Cookson, R. C.; Warrell, D. C. J.Chem.Soc. (C) 1967, 1391-1400. The literature melting point of each compound is listed in the
table above.
1

35 pts Conclusion and Discussion. Summarize the experimental results and present a well-organized discussion
in paragraph form of the supporting data that distinguished between the possible products; including the X-ray
crystal structure. Be sure to identify, by name, the stereochemistry of the product obtained. Explain the unusual
observation during melting point determination, the unusual C=O stretch in the IR, and NMR patterns observed.
Also, highlight the green chemistry characteristics of the experiment.
15 pts Additional Questions based on the X-ray Crystal Structure Data Given
1.

Bond Lengths Look up the literature bond lengths (reference your source) for the FOUR different types
of bonds in the molecule. Compare the literature bond lengths to those found in the x-ray structure of the
Diels-Alder product. How closely do they compare?

2.

Bond Angles Compare the bond angles reported in the x-ray crystal structure to those expected for a sp3
carbon and sp2 carbon (reference your source). How do they compare?

3.

J Values - The dihedral angles (torsional angles) reported for the methine and methylene hydrogens of the
product were determined by X-ray crystallography. How do these numbers compare with the J values
calculated from the 1H NMR and those predicted from the Karplus relationship? Discuss.