Question

a) Draw the mechanism (with curved arrows) for the reaction of the conjugate base of p?hydroxybenzaldehyde with methyl p?toluenesulfonate.

b) What ether would you obtain from the reaction of CH₃CH₂O^- with 1?iodopentane? Draw the structure of the product.

c) Explain in general how TBAS (Bu4N+HSO4-) works as a phase transfer catalyst in this reaction. What anion does Bu4N+ shuttle into the organic layer?

d) p-Hydroxybenzaldehyde has four signals in the NMR, with the following chemical shifts and multiplicities. Assign each peak to a set of protons in the structure shown (remember, the aromatic ring has four Hs on it also). Which peak will have the highest integration?

Peaks: 9.86 (singlet), 7.82 (doublet), 6.98 (doublet), 3.86 (singlet)

O AH OH

Answer 1