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Chapter 19: Q24P (page 1014)

Propose a mechanism for the synthesis of methyl orange.

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Step 1:

Step 2:

Step 3:

Step by step solution

01

Diazotization

Sulphanilic acid with sodium carbonate converted into sodium salt of p-amino benzene sulphonate. It undergoes diazotization reaction in presence of nitrous acid to form diazonium chloride salt.

02

Ionisation

Diazonium chloride then ionizes in aqueous solution, giving sodium ion, chloride ion and internal salt.

03

Coupling

N-N-dimethylaniline hydrochloride added to internal salt, coupling occurs to give methyl orange.

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Most popular questions from this chapter

Question. Propose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at 3-position.

Propose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at 3-position.

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(a) Explain this order:

Predict the products of the following reactions:

  1. 产耻迟补苍-2-辞苍别鈥夆赌�+鈥夆赌塪颈别迟丑测濒补尘颈苍别鈫�NaBH(OAc)3
  2. 4-fluoropyridine鈫�NaOCH2CH3
  3. 3-nitroaniline鈫�(2)CuBr(1)HCl,NaNO2
  4. butan-2-one鈫�(2)LiAlH4(1)KCN,HCN
  5. cyclopentanone鈫�(2)LiAlH4(1)aniline,H+
  6. 2-bromopentane鈫�(2)Ag2O,heat(1)(CH3)3N:

h.

i.

j.

We have considered nucleophilic aromatic substitution of pyridine at the 2-position and 3-position but not the at the 4-position. Complete the three possible cases by showing the mechanism for the reaction of methoxide ion with 4-chloropyridine. Show how the intermediate is stabilized by delocalization of the charge onto the nitrogen atom.
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