1. (10 points). Using resonance and inductive effect arguments explain why the pKa values of the five different phenols listed
below clearly). (hint: draw out the full structure of the -NO2.
are so different? (Draw all the resonance structures and explain
2. (5 points). Show all the steps necessary for the following transformations. Pay attention to directing effects when you plan
your synthesis. Note in some cases it may be impossible to avoid getting mixtures of isomeric if this is the case
3. (5 points). Why is product A observed for the Birch reduction of nitrobenzene, not Product B? Use mechanism and
resonance to answer this question.
These solutions may offer step-by-step problem-solving explanations or good writing examples that include modern styles of formatting and construction
of bibliographies out of text citations and references. Students may use these solutions for personal skill-building and practice.
Unethical use is strictly forbidden.