Textbook: Wade 7th Ed. (2009)

Chapter 16: Aromatic Compounds

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Individual Problems

Individual Problems

Problem # 582

Rationalize the follwing pK_a values. Explain your answer in terms of the stabilites of the conjugates bases of each acid.

Note: the lower the pK_a, the stronger the acid.

Solution

The benzylic proton (middle compound) is more acidic than the allylic proton (left compound) because its conjugate base is more stable. This is because it has more resonance forms.

Cyclopentadiene (right compound) is the strongest of the three because it has the most stable conjugate base. Why is it the most stable? Because it's aromatic! To be aromatic, a compound must:

be cyclic and planar
be sp² hybridized
Have a Huckel number of pi electrons- 2, 6, 10, 14, etc.

The cyclopentadienyl anion meets all of these criteria, and so is aromatic, and very stable.

Problem Details

MendelSet practice problem # 582 submitted by Matt on July 9, 2011.

Subject: Organic Chemistry

Subject Topic(s): Benzene and Aromaticity

Question Type: Concept (explain why this is so..)

Keyword(s): acid strength, benzylic position, aromaticity

Problem # 583

Pyrrole is an example of a heteroaromatic compound: it contains a heteroatom (atom that is not carbon or hydrogen, such as N, O, S, etc.), and is aromatic.

Because pyrrole is aromatic, we should be able to draw many resonance forms- usually as many resonance forms as sides (in this case, five sides, so five resonane forms).

Draw all resonance forms for pyrrole. (I've started you off.)

Solution

One of the rules for aromaticity is that all atoms shoudl be sp² hybridized. But the nitrogen in pyrrole is sp³ hybridized, so how is it still aromatic? Because in 4/5 of its resonance forms the nitrogen is sp² hybridized; the real picture of pyrrole looks more like the structure on the left (dashed circle) than any individual resonance form.

Problem Details

MendelSet practice problem # 583 submitted by Matt on July 9, 2011.

Subject: Organic Chemistry

Subject Topic(s): Benzene and Aromaticity

Question Type: Concept (explain why this is so..)

Keyword(s): resonance, aromaticity, heteroaromatic compounds

Problem # 584

Imidazole (shown below) has two nitrogen atoms, N-1 and N-3. Which nitrogen is more basic?

To answer this problem, draw the product after each nitrogen protonates, and compare their stabilities. Explain your reasoning.

Solution

Imidazole is aromatic. When N-3 protonates, the product is still aromatic.

But when N-1 protonates, the product is no longer aromatic (and therefore significantly less stable).

Because of this, N-3 is much more basic than N-1. Another way of thinking of this is that the lone pair on N-1 is involved in the aromatic circuit, and so is not available to pick up a proton.