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SolutionsNomenclature

1. Name these anilines

  1. C6H5NHCH3
  2. C6H5N(CH3)2
  3. Aniline with a Cl at position 4
  4. Aniline with two NO2 groups at positions 2 and 4
  5. CH3C6H4NH2 with the methyl group ortho
  1. N-Methylaniline.
  2. N,N-Dimethylaniline.
  3. 4-Chloroaniline (p-chloroaniline).
  4. 2,4-Dinitroaniline.
  5. 2-Methylaniline (o-toluidine).

2. Draw the structure

  1. 3-Bromo-4-methylaniline
  2. 4-Aminobenzoic acid
  3. N-Ethyl-3-nitroaniline
  4. p-Phenylenediamine
  1. Ring with NH2 at C1, Br at C3 and CH3 at C4.
  2. H2N–C6H4–COOH with both groups para; the acid is the main function and the NH2 is named as amino (PABA).
  3. Ring with NHCH2CH3 at C1 and NO2 at C3.
  4. 1,4-Diaminobenzene, H2N–C6H4–NH2.

3. Aniline or benzylamine?

Is benzylamine, C6H5CH2NH2, an aniline? What difference in basicity would you expect between the two?

No: in benzylamine the nitrogen is bonded to an sp3 carbon, not to the ring. Its lone pair is not delocalized into the ring and its basicity (pKb ≈ 4.7) is that of an aliphatic amine, about 50,000 times greater than that of aniline (pKb 9.4).

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