Diels Alder datasheet
2016
Name:
Lab Section:
Fill out this sheet BEFORE printing. Only the TLC plate should be hand drawn. Use the dropdowns for bond
type and section.
1. (21 pts) Fill in the table for the three compounds listed. Include literature sources, using proper citation
format for your data.
Compound
MW
(g/mol)
Mass
(g)
Vol
(ml)
Mols Density
g/ml
Mp
Bp
source
2,4-hexadien-1-ol
1
maleic anhydride
2
Product
-------
--------
Exp:
-----
3
Source 1:
Source 2:
Source 3:
2.(11 pts) Fill in the experimental data for your TLC analysis, including specific information for each
lane. Sf = solvent front; D1, D2, D3 = distance the spot(s) traveled; Rf-1, Rf-2, Rf-3 = Rf value for
spots. If there is only one spot in the lane, leave the D2, D3 and Rf-2 Rf-3 spaces blank.
Sample spotted
1
2
3
dSolv
D1
Rf1
D2
Rf2
D3
Rf3
Lane 3
Visualization method(s):
Lane 2
Mobile Phase:
Lane 1
Stationary phase:
3, (10 pts) Calculate the percent yield of your product and show your work in the box provided below. (No
credit will be given if work is not shown, work is not legible or if work is not kept within the allotted space.)
4. (17 pts) Infrared Spectral Results. Give the wavenumbers of the most important peaks in the IR spectrum of
both starting materials and the reaction product. Indicate what functional group gives rise to these peaks.
Do not list the position of an IR absorption as a range; IR peaks are listed by the wavenumber of maximum
absorbance. Giving a range will get no credit.
Wavenumber (cm-1)
Bond type (use dropdown)
Compound
2,4-hexadien-1-ol
2,4-hexadien-1-ol
Maleic Anhydride
Maleic Anhydride
Reaction Product
Reaction Product
Reaction Product
5 (16 pts) For the NMR Spectrum: Fill in the designated spectral data in the
table provided. Match the labeled protons in the structure of the product with
the appropriate peak in the NMR spectrum. S=singlet, D= doublet, T = triplet,
DD =doublet of doublets, DT = doublet of triplets, M=multiplet
Chemical shift (ppm)
Splitting
Hydrogen
5.81 DD
5.63 DD
4.43 DD
4.10 DD
3.38 DD
3.28 M
H7a
3.08 DD
2.65 M
2.5
1.12 D
CO2H