Question

Explain. Why nitration of benzoic acid to give meta benzoic acid

Answer 1

Answer:

3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-Nitrobenzoic acid. This compound can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.[2]

3-Nitrobenzoic acid

Skeletal formula

Ball-and-stick model

Names

Preferred IUPAC name

3-Nitrobenzoic acid

Other names

m-Nitrobenzoic acid

Identifiers

CAS Number

121-92-6 ☑

3D model (JSmol)

Interactive image

ChEMBL

ChEMBL274839 ☑

ChemSpider

8183 ☑

ECHA InfoCard

100.004.099

PubChem CID

8497

CompTox Dashboard (EPA)

DTXSID0025737 Edit this at Wikidata

InChI

InChI=1S/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10) ☑

Key: AFPHTEQTJZKQAQ-UHFFFAOYSA-N ☑

InChI=1/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)

Key: AFPHTEQTJZKQAQ-UHFFFAOYAS

SMILES

O=[N+]([O-])c1cc(C(=O)O)ccc1

Properties

Chemical formula

C7H5NO4

Molar mass

167.12 g/mol

Appearance

cream-colored solid

Density

1.494 g/cm3

Melting point

139 to 141 °C (282 to 286 °F; 412 to 414 K)

Solubility in water

0.24 g/100 mL (15 °C)

Acidity (pKa)

3.47 (in water)[1]

Magnetic susceptibility (χ)

-80.22·10−6 cm3/mol

Related compounds

Related compounds

Benzoic acid

Nitrobenzene

Anthranilic acid

3,5-Dinitrobenzoic acid

2-Nitrobenzoic acid

4-Nitrobenzoic acid

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Answer 2

Answer:

Preparation. It is prepared by nitration of benzoic acid at low temperatures. ... Since carboxylic acid functional groups are electron withdrawing, during an electrophilic aromatic substitution reaction of nitration, substituents are directed to a meta position which explains this regiochemistry.