WEEK 1 TUTORIAL: CHEM320W – Reactions of heterocyclic compounds 2022

1. Name the following compounds:

(a) 2-Methylazacyclobutane or 2-Methylazetidine

(b) 2,3-dimethylazacycohexane or 2,3-dimethylpiperidine
(c) 3-chloropyrrole
(d) 2-Ethyl-5-methylazacyclohexane or 2-Ethyl-5-methylpiperidine
(e) N-Ethyl-N-methylaniline oxide (tertiary aromatic amine oxide)
(f) Pyridium chloride (tertiary heterocylic ammonium ion)
(g) N,N-dimethylpiperidinium iodide (quaternary heterocyclic ammonium ion)
(h) N-butyl-N-ethyl-N-methyl-4-methylhexylammonium chloride
(i) N-Ethyl-N-methyl-2,3-dimethylbutanamine

2. Name the following heterocyclic compounds

3. Attempt to name the following bicyclic compounds:

4. Rank the amines in each set in order of increasing basicity:

5. List the following compounds in order from strongest to weakest acid:
6. Which of the following are capable of being resolved into enantiomers?

7. What products are formed when N-ethylaniline is treated with each reagent
8. Propose the products of the following acid-base reactions and in each case explain
whether the products or reactants are favored (hint: Use values of pKa from your pKa
tables).
9. Draw the products formed when each amine is treated with (1) excess CH3I, followed by
(2) Ag2O and heat. Indicate the major product when a mixture results.
10. Draw the products of each of the following reactions: