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Show how p-toluidine can be converted to the following compounds, using any necessary reagents.

Short Answer

Expert verified

p-toluidine on treatment with sodium nitrite and hydrogen chloride undergoes diazotisation reaction in which amino group gets converted to diazonium salt which acts as a leaving group and in next step, on treatment with copper(I) cyanide, cyano group gets substituted at the carbon to which nitrogen is attached and nitrogen leaves as a leaving group which leads to formation of required product.

Step by step solution

01

Step-1. Explanation of part (a):

p-toluidine on treatment with sodium nitrite and hydrogen chloride undergoes diazotisation reaction in which amino group gets converted to diazonium salt which acts as a leaving group and in next step, on treatment with copper(I) cyanide, cyano group gets substituted at the carbon to which nitrogen is attached and nitrogen leaves as a leaving group which leads to formation of required product.

02

Step-2. Explanation of part (b):

p-toluidine on treatment with sodium nitrite and hydrogen chloride undergoes diazotisation reactionin which amino group gets converted to nitrogen which acts as a leaving group and in next step, on treatment with copper(I) cyanide, cyano group gets substituted at the carbon to which nitrogen is attached and nitrogen leaves as a leaving group and further treatment with lithium aluminum hydride and water, reduction of cyano group takes place to methylamine.

03

Step-3. Explanation of part (c):

p-toluidine on treatment with sodium nitrite and hydrogen chloride undergoes diazotisation reactionin which amino group gets converted to nitrogen which acts as a leaving group and in next step, on treatment with potassium iodide, iodide ion acts as a nucleophile and attacks at the carbocation which is formed after elimination of nitrogen as leaving group and required product is formed.

04

Step-4. Explanation of part (d):

p-toluidine on treatment with sodium nitrite and hydrogen chloride undergoes diazotisation reactionin which amino group gets converted to nitrogen which acts as a leaving group and in next step, on hydrolysis, hydroxyl group gets attached to the carbocation which is formed after removal of nitrogen and required product is obtained.

05

Step-5. Explanation of part (e):

p-toluidine on reaction with acetyl chloride undergoes acetylation reaction in first step of the amino group and further reaction with concentrated sulphuric acid and nitric acid, nitration reaction takes place in which nitro group gets attached to the ring and on work up, the acetanilide group gets reduced to the amino group and required product is obtained.

06

Step-6. Explanation of part (f):

p-toluidine on reaction with cyclopentanone in presence of sodium acetoxyborohydride and acetic acid undergoes condensation reaction which leads to formation of required product.

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Most popular questions from this chapter

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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