Question

I need help with both the parts please.

c. Interestingly, when compared to benzoic acid, p-methoxybenzoic acid is less acidic and m- methoxybenzoic acid is more acidic. Please explain how the location of the methoxy groups influences the pk of each isomer relative to benzoic acid using drawings and a minimum amount of words. TIP: How stable is each conjugate base? What is or isn't stabilizing it? TIP #2: EAS/Aromaticity has nothing to do with it. oglegt increasing acidity d. Which reaction would proceed faster and why? Use drawings and 20 words or less to describe your answer. TIP: See your lecture notes Rxn A: NaOH, H2O tamme one NaOH, 130. io Rxn B HCI, H,O

Answer 1

PART C

Acidity is measure of stability of its conjugate anion

electron releasing group deceases the stability of anion hence acidic character decreases

electron withdrawing group increases the stability of anion hence acidic character increases  

OMe shows +M i.eelectron releasing through resonance at ortho and para position. when OMe is present at para position it increases the electron density which decreases the acidic character

whereas no +M takes place at meta position only -I of OMe is considered hence it increases the acidic character

hence order will be p-methoxybenzoic acid < benzoic acid < meta-methoxybenzoic acid

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