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pounds
Saylor E. Jessop; Langdon Martin, PhD
OH
ABSTRACT: Synthesis of two benzene compounds to air dry overnight on a watch glass.
was attempted with bromobenzene as the starting
material. The initial intended product, 2-(para-nitro-
phenyl)-1-propene, was to be synthesized via nitra-
tion of bromobenzene followed by a Grignard reac-
tion with acetone and reaction with sulfuric acid to conc. Acid
produce the alkene. Upon multiple failed attempts at
getting the Grignard reaction to start, the intended
product was altered. The nitro group of para-
bromonitrobenzene was reduced using Sn-Cl2. 0.498
g of para-bromoaniline were isolated and confirmed Figure 1. Reaction of bromobenzene with concentrated
with NMR results after a purification. sulfuric acid and concentrated nitric acid to produce para-
bromonitrobenzene.
Figure 4. 1H NMR spectra of unpurified product from the reduction of the nitro group in
para-bromonitrobenzene.
Figure 5. Literature 1H NMR spectra of para-bromoaniline
Figure 6. 1H NMR spectra of purified para-bromoaniline from the reduction of the nitro
group in para-bromonitrobenzene
CONCLUSION
Despite several attempts, the intended products were not
successfully synthesized. Reaching the original product, 2-
(para-nitrophenyl)-1-propene, was obstructed by the failure of
the Grignard reaction to start. Future attempts at synthesizing
this molecule would perhaps include maintaining greater at-
tention to keeping the ether anhydrous and using a pure
para-bromonitrobenzene for the formation of the Grignard
reagent. It was also suggested that this molecule may just not
make an efficient substrate for this type of reaction.
The new target was also not fully completed, although the
nitro group on the para-bromonitrobenzene was successfully
reduced to form para-bromoaniline of a reasonable purity.
However, time constraints disallowed doing a melting point
analysis and the synthesis procedure could not be continued
to add an isopropyl group to the amine group of para-bro-
moaniline, which would have been carried out with acetone.
While disappointing that these synthetic targets could not be
fully reached, the experience was still a rewarding one and
involved a high level of independence, quick thinking, and
perseverance. A greater comfort level with standard organic
reactions and methodologies was also achieved.
ACKNOWLEDGMENT
I would like to thank Langdon Martin for his unending pa-
tience during this entire project. With every roadblock he was
there to provide answers and he juggled a dozen students at
once with grace. Thanks for an awesome year full of learning!
REFERENCES
1. L. Martin. Electrophilic Aromatic Substitution: Synthesis
of a Bromonitrobenzene Isomer. 2015.
2. L. Martin. The Grignard Reaction: Synthesis of a Ter-
tiary Alcohol. 2016.