(a) Interpretation: It is to be explained why the pKa values of all three isomers in which a methyl group is attached to the ring are higher than the pKa of phenol itself. Concept introduction: When comparing uncharged acids, the stronger acid is the one whose negatively charged conjugate base is more stable. Electron donating substituents attached to the ring decrease the acidity as compared to non-substituted rings. Alkyl group is an electron donating group, thus, it will destabilize the negatively charged conjugate base to a greater extent than non-substituted rings.

Question

8 00 6 = 10 10 Decide whether each of the molecules in the table below is stable, in the exact form in which it is drawn, at pH = 11. If you decide at least one molecule is not stable, then redraw one of the unstable molecules in its stable form below the table. (If more than unstable, you can pick any of them to redraw.) Check OH stable HO stable Ounstable unstable O OH stable unstable OH 80 F6 F5 stable Ounstable X Save For Later Sub 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy C ཀྭ་ A F7 매 F8 F9 4 F10

Answer 1

Question

Chapter 6, Problem 6.77P

Interpretation Introduction

(a)

Interpretation:

It is to be explained why the pKa values of all three isomers in which a methyl group is attached to the ring are higher than the pKa of phenol itself.

Concept introduction:

When comparing uncharged acids, the stronger acid is the one whose negatively charged conjugate base is more stable. Electron donating substituents attached to the ring decrease the acidity as compared to non-substituted rings. Alkyl group is an electron donating group, thus, it will destabilize the negatively charged conjugate base to a greater extent than non-substituted rings.

Interpretation Introduction

(b)

Interpretation:

Why the meta isomer has the lowest pKa value of the three isomers is to be explained.

Concept introduction:

When comparing uncharged acids, the stronger acid is the one whose negatively charged conjugate base is more stable. Electron donating substituents attached to the ring decrease the acidity as compared to non-substituted rings. Methyl groups is an electron donating group, thus, it will destabilize the negatively charged conjugate base to a greater extent than non-substituted rings. Greater the resonance stabilization of the conjugate base, stronger is the acid. In the resonance contributors, the structure in which an atom bearing a negative charge becomes destabilized as the number of electron-donating groups attached to it increases. This structure will not contribute significantly to the resonance hybrid.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

8 00 6 = 10 10 Decide whether each of the molecules in the table below is stable, in the exact form in which it is drawn, at pH = 11. If you decide at least one molecule is not stable, then redraw one of the unstable molecules in its stable form below the table. (If more than unstable, you can pick any of them to redraw.) Check OH stable HO stable Ounstable unstable O OH stable unstable OH 80 F6 F5 stable Ounstable X Save For Later Sub 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy C ཀྭ་ A F7 매 F8 F9 4 F10

Just try completing it and it should be straightforward according to the professor and TAs.

The grading is not on correctness, so if you can just get to the correct answers without perfectionism that would be great. They care about the steps and reasoning and that you did something. I asked for an extension, but was denied the extension.