Question

Question: Draw the three possible resonance structures for an acid bromide, . Then, using the p^K_a values in Appendix A, decide if RCOBr is more or less stabilized by resonance than a carboxylic acid (RCOOH).

Short answer

Answer

RCOBr is less stabilized by resonance than RCOOH.

Step-by-step solution

Step-by-Step SolutionStep 1: Resonance structures

Resonance structures are the combination of various Lewis structures used to represent the delocalization (movement) of electrons.

Resonance structures of acid bromide

The resonance structures of acid bromide are provided below:

Comparing the stability of acid bromide and carboxylic acids

The bromine atom is less basic than the hydroxide group and does not donate its electrons easily. Hence it contributes very little towards the resonance hybrid compared to the hydroxyl group.

Therefore, RCOBr is less stabilized than RCOOH.