Relative reactivity of carboxylic acid derivatives

At this point we want to consider the relative reactivity of carboxylic acid derivatives and other carbonyl compounds in general terms. We return to the subject in more detail in Chapter 7. Let us first examine some of the salient structural features of the carbonyl compounds. The strong polarity of the C=0 bond is the origin of its reactivity toward nucleophiles. The bond dipole of the C-X bond would be expected increase carbonyl reactivity as the group X becomes more electronegative. There is another powerful effect exerted by the group X, which is resonance electron donation. 

Fig. Relative reactivity of carboxylic acid derivatives. Electronic Factors...

The relative reactivity of carboxylic acid derivatives was discussed in Chapter 10. 

Relative reactivities of carboxylic acid derivatives toward nucleophilic acyl substitution. A more reactive derivative may be converted to a less reactive derivative by treatment with an appropriate reagent. Treatment of a carboxylic acid with thionyl chloride converts the carboxylic acid to the more reactive acid chloride. Carboxylic acids are about as reactive as esters under acidic conditions, but are converted to the unreactive carboxylate anions under basic conditions. 

RELATIVE REACTIVITIES OF CARBOXYLIC ACID DERIVATIVES (RCOLG)... 

We begin with a comparison of the structures, properties, and relative reactivities of carboxylic acid derivatives. We then explore the chemistry of each type of compound. Halides and anhydrides are valuable reagents in the synthesis of other carbonyl compounds. Esters and amides are enormously important in nature for example, the esters include common flavoring agents, waxes, fats, and oils among the amides we find urea and penicillin. The alkanenitriles, RC=N, are also freated here because they have similar reactivity. 

Relative Reactivities of Carboxylic Acid Derivatives in Nucleophilic Addition-Elimination with Water... 

Working with the Concepts Relative Reactivity of Carboxylic Acid Derivatives... 

---