Rationalize the follwing pKa values. Explain your answer in terms of the stabilites of the conjugates bases of each acid.
Note: the lower the pKa, the stronger the acid.
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.)
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.
Use curved arrows to draw a mechanism for the generic electrophilic aromatic substitution (EAS) reaction below.
A chemist tried to prepare compound A from benzene via Friedel-Crafts alkylation and instead produced compound B.
Why did this happen? How could the chemist prepare compound A?
Phenol can be prepared from benzene and hydrogen peroxide in the presence of a really strong acid. Propose a mechanism for this reaction.
Indicate the eletrophile formed by each set of reagents/conditions below.
Draw the structure of the major organic product from each reaction sequence.
Show how to prepare vinyl benzene from benzene.