Introduction COCH, H2SO NO methyl benzoate methyl 3-nitrobenzoate The nitration

Question

Introduction COCH, H2SO NO methyl benzoate methyl 3-nitrobenzoate The nitration of methyl benzoate is a typical electrophilic aromatic substitution reaction. In the first step of the reaction a nitronium ion (NO2) is formed by the reaction of nitric acid and sulfuric acid The nitronium ion acts as the electrophile and reacts with the aromatic ring at the position where the electron density is the greatest. The non-aromatic carbocation intermediate is stabilized by resonance structures. The reaction is completed by proton loss from the nitro- bearing carbon, regenerating the aromatic ring and giving the substitution product. In an electrophilic aromatic substitution reaction in which a second substituent is added to a monosubstituted benzene ring, three isomers are possible. designated ortho, meta. or para. In the case of the nitration of methyl benzoate the three possibilities are shown below. a, o NO, NO NO, medryl 2-nitrobenzoete mp-13 °C medhyl 3-nitarobenzcale methyl 4-aitrobeneoane mp 78-80°C mp 94-96 C The site of substitution of the second substituent is determined by the first substituent. These substituents may be divided into two groups. One directs the second substituent into the ortho or para positions. These ortho.para directors include donating groups such as alkyl groups, bydroxyl groups. and halogens. The second group directs the second substituents into the meta position and includes electron withdrawing substituents such as esters, carboxylic acid, and nitro groups. If we look at the resonance structures of the intermediate, the meta rather than ortho or

Explanation / Answer

3.

There are three ( 3 ) different protons in methyl-4-nitrobenzoate

4.

Molar mass of methyl benzoate = 136.15 g/mol

Moles of methyl benzoate = mass / molar mass = 0.600 / 136.15 = 0.00441 mol

From the balanced equation,

0.00441 mol of methyl benzoate forms 0.00441 mol of methyl-4-nitrobenzoate

Mass of methyl-4-nitrobenzoate = moles * molar mass = 0.00441 * 181.15 = 0.7983 g.

(a)

5.

(C) NO2+ nitronium ion is an electrophile.

Related Questions

Navigate

• Browse (All)
• Browse I
• Subjects

---

---

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