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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1/2 - 51% + » GAY Organic Reactions Assignment /26 Write the type of reaction that is occurring on the line provided then complete the reaction. Only include the major products and any byproducts (e.g. H₂O) but no minor products. Please use either full structural diagrams or the combination method shown in the lesson. Skeletal/line diagrams will not be accepted. H3C 1. 2. CH3 A Acid OH Type of Reaction: NH Type of Reaction: + H₂O Catalyst + HBr 3. Type of Reaction: H3C 4. Type Reaction: 5. H3C CH2 + H2O OH + [0] CH3 Type of Reaction: 6. OH CH3 HO CH3 + Type of Reaction: 7. Type of Reaction: + [H]

Answer 1

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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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