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Chapter 25: 51 (page 1043)

How would you separate toluene (C6H5CH3 ), benzoic acid (C6H5CO2H ), and aniline (C6H5NH2 ) by an extraction procedure?

Short Answer

Expert verified

The mixture of benzoic acid, aniline, and aniline can be extracted with the help of water and dichloromethane.

Step by step solution

01

Acid-base reaction

The reaction in which the acid donates a proton to the base (accepts a proton) is termed as the acid-base reaction.

02

Explanation

The mixture is composed of benzoic acid, aniline, and aniline. All are soluble in dichloromethane and water.

When an acid is added to the mixture, aniline (base) abstracts a proton to form a conjugate acid. So,

  • Insoluble 鈥� dichloromethane
  • Soluble 鈥� water

When a base is added to the mixture, the benzoic acid (acid ) loses a proton to form a conjugate base. So,

  • Insoluble 鈥� dichloromethane
  • Soluble 鈥� water

In the above-mentioned way, the mixture of benzoic acid, aniline, and aniline can be extracted.

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Most popular questions from this chapter

Question: Which N atom in each compound is more basic? What product is formed when each compound is treated with HCl?

a.

b.

Draw the products formed when p-methylaniline ( p-C6H4NH2) is treated with each reagent.

  1. HCl
  2. CH3COCl
  3. CH3CO2O
  4. Excess CH3I
  5. CH32C=O
  6. CH3COCl,AlCl3
  7. CH3CO2H
  8. NaNO2,HCl
  9. Part (b), thenCH3COCl,AlCl3
  10. CH3CHO,NaBH3CN

Question: Give a systematic or common name for each compound.

Tertiary ( 3掳) aromatic amines react with NaNO2 and HCl to afford products of electrophilic aromatic substitution. Draw a stepwise mechanism for this nitrosation reaction and explain why it occurs only on benzene rings with strong ortho, para activating groups.

Question: Which nitrogen atom in each compound is more basic?

a.

b.
See all solutions

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