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and 3 alkyl halides give low/no yields in this and similar carbanion (enolate) alkylations? What is
the predominant product? Do you expect benzyl bromide to be reactive toward enolate anions?
2. Why might someone running this experiment detect, by GC-MS analysis, a product with a molecular weight of
272? Draw a structure for this product.
3. Use resonance structures to explain why diethylmalonate may be easily deprotonated.
References:
1. Thompson Douglas L.; Reeves Perry C. Phase-Transfer-Catalyzed Alkylation of Ethyl
Acetoacetate and Diethyl Malonate Journal of Chemical Education, volume 62, number 10, 1985.
pp907-8.
2. Williamson Kenneth L. Macroscale and Microscale Organic Experiments D. C. Heath and Co.
Mass, 1989. pg. 533.
3. Mackay, K. M.; Mackay R. A. Introduction to Modern Inorganic Chemistry 4th ed. Prentice Hall,
Englewood cliffs, NJ 1989. pp 157-62.
4. Miller, James M. Chromatography Concepts and Contrasts : John Wiley and sons, New York,
1988, pp. 109-153.
5. M
c
Murry, John Organic Chemistry Brooks/Cole Co. 1984 pp. 832-7, 617-18.
6. Brandstrom, Arne; Junggren, Ulf Tetrahedron Letters no. 6, pp 473-474, 1972.
Synthetic Experiment PreLab Grading Sheet
Name(s):
TA:
Date:
PreLab For Exp't # 13
Phase-Transfer-Catalyzed Alkylation of Diethyl Malonate
Possible Missed
Points Points
Date, Name, Desk #, Experiment # & Title(abbreviated after 1
st
pg), Section &
TA Name
4
Summary
8
Goals
8
Reactions, structures, conditions, diagrams
14
Completeness of Chemical Data Table(s)
14
Chromatographic Behavior Comparison
16
Spectral Features Comparison
12
Work-up - Explanation of the product isolation and purification process
12
PreLab Questions
12
TOTAL FOR PRELAB
100
Date Handed in:
General Comments: Total Points:
Synthetic Experiment Final Report Grading Sheet
Name:
TA:
Date:
Final Report For Exp't # 13
Phase-Transfer-Catalyzed Alkylation of Diethyl Malonate
Possible Missed
Points Points
Name, Date, Experiment Title (abbreviated after 1st page) and every page
numbered
4
OBSERVATIONS and DATA - Overall organization, readability, completeness
8
Data: Weighing data, molecular weights, moles, density, volumes, refractive
index,
Product analysis conditions i.e. gas chromatographic analysis conditions sheet
for GC and/or GC-MS, weight of sample and KBr for IR; solvent and field
strength for NMR; ionization mode for MS;
12
Yield: Show % yield calculations with limiting reagent clearly stated.
Indicators of product purity such as gas chromatograms or TLC, boiling point
or refractive index.
12
RESULTS AND DISCUSSION - Overall organization, readability, completeness 8
Results; Achievement of goals
16
Product Analysis Data: Quality and Interpretation Structures assigned to all
gas chromatogram peaks and structures written on the corresponding mass
spectra from GC-MS. Structure(s) drawn and interpreted on the product
spectrum. Calculate relative %s of isomers, by-products or starting materials
from GC peak areas.
Interpret major MS or IR peaks or all NMR peaks (including impurities).
Explain how spectra confirm product identity.
See Lab Guide Chapter 3, Section 3.4 for guidelines in annotating spectra and
Ch 11 for help with interpretation.
24
POSTLAB QUESTIONS
16
TOTAL POINTS
100
Date Handed in:
General Comments: Total Points: