Discussion
Consider the following pairs of carbonyl compound and its approximate wavenumber.
Anhydride - 1800 and 1760
Ester - 1735
Ketone - 1715
Amide - 1780
How many of the pairs given above are correctly matched?
Answer: A
The first three are correct and the fourth is badly wrong: an amide absorbs near 1650, the lowest of the family, because the nitrogen's lone pair delocalises into the carbonyl. Ordering the family by how much the adjacent atom donates or withdraws - anhydride highest, amide lowest - turns eight remembered numbers into one pattern that can be reconstructed when a value is forgotten. Naming the cost of a choice alongside its benefit is what turns a fact into a design decision.
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