Experiment 6: Nitration of 4-hydroxyphenylacetic acid: Synthesls of a naturally-

Question

Experiment 6: Nitration of 4-hydroxyphenylacetic acid: Synthesls of a naturally-occurring nitro compound NO2 HOAc, HNO 4-hydranyphenylacetic acid REQUIRED READING Technique 6: Heating and cooling methods, section 6.9 Technique 9: Physical constants of solids: the MP Technique 11: Crystallization: purification of solids Technique 25: Infrared spectroscopy, section 25.4 Technique 26: Nuclear magnetic resonance page 63 page 99 page 118 page 306 page 342 RECOMMENDED KLEIN READING 19.1 Introduction to electrophilic aromatic substitution, page 875 19.4 Nitration, page 882-883 19.7 Activating groups, page 889-893 INTRODUCTION Natural products containing nitro groups have been isolated from plants, fungi, bacteria and mammals. These compounds display great structural diversity and they exhibit a wide range of biological activities including antibiotic, antitumor and cell signaling properties The most prolific natural source of monocyclic, nitrated aromatic compounds is the psychrotolerant, gram-negative bacterium Salengentibacter sp. strain T436, which is found in Arctic pack ice. Thus far, a total of 21 monocyclic, nitroaromatic compounds have been isolated from cultures of this microorganism grown in complex media dissolved in artificial sea water. The fermentations were optimized for the production of bioactive, secondary metabolites, and it is not known whether the bacterium produces the compounds in its native habitat. Four different metabolites are shown below. A number of these compound exhibit antimicrobial and cytotoxic activities, with 2-nitro-4-(2'- nitroethenyl)phenol (1) being the most potent. Compounds 2 and 3 are antimicrobial, whereas compopund 4 is cytotoxic. For experiment 5, compound 4 will be synthesized. NO2 O2N OH antdfungal and antbacterial ytotaxic against lymphooylic antifungal most potent, antfungal, anibacterial and cylotaxic leukernia cels

Explanation / Answer

In this reaction 4-hydroxyphenyl acetic acid react with glacial acetic acid and nitric acid to form 2-(4-hydroxy-3-nitrophenyl)acetic acid.

Here acetic acid and nitric acid are used excess. One molecule of 4-hydroxyphenylacetic acid to form one molecule of the product. So one mole react to form one mole product. So we can calculate as follows.

Molecular mass of 4-hydroxyphenylacetic acid = 152.15

Molecular mass of 2-(4-hydroxy-3-nitophenyl)acetic acid = 197.146

Weight of 4-hydroxyphenylacetic acid used = 2g

Moles of 4-hydroxyphenylacetic acid = 2 / 152.15 = 0.013145 mol

So 0.013145 Mol's of product should form theoretically

So theoretical yield of product is = moles × molecular mass

= 0.013145 × 197.146 = 2.59 g.

Related Questions

Navigate

• Browse (All)
• Browse E
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.