Discussion Section 5: Nucleophilic Aromatic Substitution and Carbonyl Chemistry
1. Intelence is an anti-HIV drug currently used clinically and has been shown to be active against several
double mutant strains of HIV. Fill in the missing reagents for each step in the reaction scheme below.
2. Predict the products of the following Birch reductions. Provide a mechanism which accounts for
product formation.
3. Provide a mechanism which accounts for the formation of D-glucopyranose from D-glucose.
4. Rank the following molecules in order of increasing electrophilicity. Justify your answer.
5. The 1H NMR and IR spectra of an unknown aromatic compound are shown. Identify the molecule and
assign the resonances found in the NMR spectrum. Propose a synthesis of this molecule starting from
benzene.
3H
1H
5H
2H
1H