Chapter 26: Problem 641
Devise a synthesis of "Diamine Green B" based on nitrobenzene, aniline, phenol, and H-acid.
Chapter 26: Problem 641
Devise a synthesis of "Diamine Green B" based on nitrobenzene, aniline, phenol, and H-acid.
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Get started for free(a) Besides destabilizing the anilinium ion, how else might a nitro group affect basicity? (b) Why does the nitro group exert a larger base-weakening effect from the para position than from the nearer meta position?
N, N, 4- Trimethylaniline has \(\mathrm{K}_{\mathrm{B}}\) of \(3 \times 10^{-9}\), quinuclidine has \(\mathrm{K}_{\mathrm{B}}=4 \times 10^{-4}\) and benzoquinuclidine has \(\mathrm{K}_{\mathrm{B}}=6 \times 10^{-7}\). What conclusions may be drawn from these results as to the cause(s) of the reduced base strength of aromatic amines relative to saturated aliphatic or alicyclic amines? Explain.
A compound \(\mathrm{A}\) has the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{4} \mathrm{BrClO}\). Treatment of A With diazomethane gave B, which upon heating with silver oxide and water was converted to another compound, C, \(\mathrm{C}_{8} \mathrm{H}_{7} \mathrm{BrO}_{2}\). The nmr spectrum of \(\mathrm{C}\) is as follows: \(\delta 2.7\) singlet, \(\mathrm{A}=2 ; \delta 7.0 \mathrm{multiplet}, \mathrm{A}=4 ; \delta 12.0\) singlet, \(\mathrm{A}=1 .\) What are the structures of compounds \(\mathrm{A}, \mathrm{B}\) and \(\mathrm{C}\) ?
Suggest the syntheses of (a) \(\beta\) -naphthol from naphthalene (b) Orange II from \(\beta\) -naphthol and sulfanilic acid.
Beginning with nitrobenzene, how would you synthesize the following compounds? (a) Bromobenzene (b) Benzonitrile
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