Synthesis of P-Bromoaniline

1479 Words May 4th, 2013 6 Pages
EXP-10 CHEM 233L
SYNTHESIS OF p-BROMOANILINE
Introduction:

In this experiment, p-bromoaniline was synthesized in three steps starting from aniline. Since the amino group of aniline is a strong activator of aromatic ring, direct bromination is impractical (equation 1). In order to make a desired product, amino group needed to be protected as the acetamide which also maintained ortho and para position but slowed down the rate of reaction (equation 2). Slow reaction rate would increase the possibility of obtaining the para-position product (equation 3). The acetamide can be hydrolyzed back to the amine (equation 4). This strategy of protection and deprotection is a very important tool in organic chemistry, especially in
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7. Remove the charcoal by hot gravity filtration ,using two pieces of fluted filter paper. To avoid contaminating the filtrate with charcoal, do not overflow the filter funnel. 8. After recrystallization, wash the crystals again with small volumes of cold water. 9. Dry the product, obtain an IR and melting point. 10. The typical yield is 2.0 g. Submit 100mg of your product and the rest for the next experiment. Table of physical data EXP-10B:
|Compound |Molecular |Amount |Density (g/ml) |Moles |Melting point |Boiling point |
| |Weigh (g) | | | |m.p.oC |b.p.oC |
|[pic] |135.165 |---- |1.219 |---- |114.3 |304 |
|Bromine |159.808 |1.5 ml |3.119 |0.0293 |-7.2 |58.7 |
|Acetic acid |60.052 |2.0 ml |1.049 |0.0349 |16.6 |117.9 |
|Solvent | | | | | | |
|[pic] |214.061 | | | |165-166 | |
|p-Br-acetanilide | | |

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