Chlorobenzene, bromination nitration

Chlorobenzene and bromobenzene, for example, undergo nitration at a rate approximately 30 times slower than benzene. The relative percentages of monosubstituted products that are obtained when chlorobenzene is chlorinated, brominated, nitrated, or sulfonated are shown in Table 15.1. 

Suzuki, H. and Mori, T. Ozone-mediated nitration of chlorobenzene and bromo-benzene and some methyl derivatives with nitrogen dioxide - High ort/io-Directing trends of the chlorine and bromine substituents, J. Chem. Soc., Perkin Trans. 2, 479-484, 1994. 

As would be expected, deuterium exchange between nitromethane and D2O is catalyzed by acetate ions, and the rate of exchange is equal to the rate of bromination under the same conditions (Reitz, 43). Similar correspondences would be expected in the rate of racemization of optically active nitro compounds, but here the position has been complicated by reports (Kuhn and Albrecht, 45 Shriner and Young, 46) that these compounds do not lose their activity completely on conversion to the ion. However, it has recently been shown (Kornblum et al., 47, 48) that the residual activity in these observations was due to the presence of alkyl nitrate as an impurity. The mutarotation of a-nitro camphor represents a similar type of reaction it is catalyzed both by acids and bases (Lowry, 49), and a quantitative study of acid catalysis in chlorobenzene solution has been made (Bell and Sherred, 50). Lowry and most subsequent writers have supposed that the observed change of rotation is due to conversion to the aci-nitro form (II), i.e.,... 

The reaction of p-chlorobenzene diazonium ion with 1-naphtholate-4-sulphonic-2-d acid is not catalysed by pjnidine and does not show an isotope efifect (Ernst et al., 1958). It corresponds therefore to Melander s nitrations and brominations (ig[B]/I i 1). 

Black liquor (pape mfq) Bone Acid Bromine Vlfeter Calcium Chloride Calcium Hypochiome Calcium Nitrate Calcium Sulfate Carbon Disulfide Carbon Tetrachloride Chtoroacetic Acetic Chioroacetic Acid—Giaciat Chlorobenzene... 

Write the structure(s) of the major product(s) that you expect from each of the following electrophilic aromatic substitutions, (a) Snlfonation of methoxybenzene (anisole) (b) bromination of nitrobenzene (c) nitration of benzoic acid (d) Friedel-Crafts acetylation of chlorobenzene. 

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