Name the following:

c.

d.

Name the following:

e.

Name the following:

f.

Why is the conjugate acid of morpholine more acidic than the conjugate acid of piperidine?

Draw the product of each of the following reactions:

b.

Draw the product of each of the following reactions:

d.

Explain why cyclopentadiene (pK_a = 15) is more acidic than pyrrole (pK_a ∼17), even though nitrogen is more electronegative than carbon.

When pyrrole is added to a dilute solution of D₂SO₄ in D₂O, 2-deuteriopyrrole is formed. Propose a mechanism to account for the formation of this compound.

Draw the product formed when pyridine reacts with ethyl bromide

How do the mechanisms of the following reactions differ?

Propose a mechanism for the following reaction:

What other product is formed in this reaction?

Rank the following compounds from easiest to hardest at removing a proton from its methyl substituent:

Rank imidazole, pyrrole, and benzene from most reactive to least reactive toward electrophilic aromatic substitution.

Imidazole boils at 257 °C, whereas N-methylimidazole boils at 199 °C. Explain the difference in boiling points.

Why is imidazole a stronger acid (pK_a ~ 14.4) than pyrrole (pK_a ~ 17)?

What percent of imidazole is protonated at physiological pH (7.4)?

Why is protonated pyrimidine (pK_a = 1.0) more acidic than protonated pyridine (pKa = 5.2)?

What are the products of the following reactions?

a.

What are the products of the following reactions?

b.

What are the products of the following reactions?

d.

What are the products of the following reactions?

e.

What are the products of the following reactions?

g.

What are the products of the following reactions?

i.

Rank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction:

One of the following compounds undergoes electrophilic aromatic substitution predominantly at C-3, and one undergoes electrophilic aromatic substitution predominantly at C-4. Which is which?

Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl₃.

a. What are the major and minor products of the following reaction?

b. Would you expect epoxides to undergo similar reactions?

Pyrrole reacts with excess para-(N,N-dimethylamino)benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.

Name the following:

a.

b.

Name the following:

c.