Look at the imide, the nitrogen analog of an anhydride below: a) For a neutral imide, will the carbonyl carbon be more (easier to attack) or less (harder to attack) electrophilic than the C of a neutral anhydride? Talk about electronegativties of Nitrogen (imide) vs Oxygen (anyhydride) b) If the imide is hydrolyzed under acidic conditions, which atom, one of the oxygens or the nitrogen, will be protonated? Explain your answer. Talk about pka and keq.

Rank the following in order of increasing basicity. The first compound in your list should be the least basic N. エZ

The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with the following electrophile followed by acid workup when relevant: CN Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed. Note: the eraser tool can be used to erase bonds, and atoms can be moved by selecting them with the selector tool and then dragging the selected atom(s) to a new position. If you make a mistake, you can use Ctrl-Z or the Undo tool. EtO H3C CN Edit Drawing OEt

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