Without looking at Table 24 2, rank the following compounds in order of ascending basicity (a) p Nitro aniline, p aminobenzaldehyde, p Bromoaniline (b) p Chloroanilinc, p aminoacetophenone, p methyl aniline (c) p (Trifluoromethyl) aniline, p methyl aniline, p (fluoro methyl)aniline Table 24 2 Base Strength of Some p Substituted Anilines NH2 H20 NH3 OH Substituent, Y pKa NH2 Stronger base 6 15 5 34 Activating groups OCH3 CH3 5 08 4 63 3 98 Ci Br 3 86 Deactivating groups CN 1 74 Weaker NO2 1 00 base

Question: Without looking at Table 24.2, rank the following compounds in order of ascending basicity. (a) p-Nitro aniline, p-aminobenzaldehyde, p-Bromoaniline (b) p-Chloroanilinc, p-aminoacetophenone, p-methyl aniline (c)

Without looking at Table 24.2, rank the following compounds in order of ascending basicity.

(a) p-Nitro aniline, p-aminobenzaldehyde, p-Bromoaniline

(b) p-Chloroanilinc, p-aminoacetophenone, p-methyl aniline

Table 24.2 Base Strength of Some p-Substituted Anilines -NH2 + H20 NH3

Table 24.2 Base Strength of Some p-Substituted Anilines -NH2 + H20 NH3 "OH Substituent, Y pKa -NH2 Stronger base 6.15 5.34 Activating groups -OCH3 -CH3 5.08 4.63 3.98 -Ci -Br 3.86 Deactivating groups -CN 1.74 Weaker -NO2 1.00 base

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