Draw the products of the two step reaction sequence shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. OH

Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C. ... NH2 HCI/H₂O reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. + 4 n [ ?

↑ k 个 G Draw the major product from this reaction. Use wedge and dash bonds to indicate relative stereochemistry where appropriate. Ignore acid byproduct. 1. Br2, H₂O 2. NaOH < Q

2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OH