p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have a pKa of 7.15 but 3,5-dimethyl-4-nitrophenol has pKa of 8.25. Why 3,5-dimethyl-4-nitrophenol is much less acidic is to be explained. Concept introduction: Resonance delocalization occurs only when the molecule is planar facilitating the overlapping of the orbitals. If the substituent groups present prevent co-planarity of the molecule then resonance is not possible. pKa = -log Ka, where Ka is the dissociation constant of the acid. Thus a stronger acid has a low pKa value. To explain: Why 3,5-dimethyl-4-nitrophenol is much less acidic with pKa of 8.25 when compared to p-nitrophenol and 2,6-dimethyl-4-nitrophenol both of which have a pKa of 7.15.

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PLEASE READ!!! I DONT WANT EXAMPLES, I DONT WANT WORDS OR PARAGRAPHS FOR THE MECHANISM!!! THANKS First image: QUESTION 6. I have to show, with ARROWS and STRUCTURES, the mechanism of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primary. I also tried to draw the mechanism, tell me what to change. Please note that its an AMIDE thats formed not an AMINE the nitrogen has ONE hydrogen and one Phenyl-C-Phenyl. I already asked for this mechanism and got as a final product ...-NH2 not whats shown on the picture, thank you Ths second part. QUESTION 3. I just need a way to synthesize the lactone A, I already started please continue from where I left it Second image: I simply need the products, substrates or reagents, thank you

Answer 1

Question

Chapter 17.SE, Problem 64AP

Interpretation Introduction

Interpretation:

p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have a pKa of 7.15 but 3,5-dimethyl-4-nitrophenol has pKa of 8.25. Why 3,5-dimethyl-4-nitrophenol is much less acidic is to be explained.

Concept introduction:

Resonance delocalization occurs only when the molecule is planar facilitating the overlapping of the orbitals. If the substituent groups present prevent co-planarity of the molecule then resonance is not possible.

pKa = -log Ka, where Ka is the dissociation constant of the acid. Thus a stronger acid has a low pKa value.

To explain:

Why 3,5-dimethyl-4-nitrophenol is much less acidic with pKa of 8.25 when compared to p-nitrophenol and 2,6-dimethyl-4-nitrophenol both of which have a pKa of 7.15.

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