310 - Practice Problem 3-10 Answer The compound ninhydrin...

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Practice Problem 3-10 Answer The compound ninhydrin exists as a hydrate. Which carbonyl group is hydrated? Explain, and give the structure of the hydrate. Hydration occurs at the central carbonyl group, which is more a more reactive electrophile than the other two carbonyl groups. The central carbonyl group is bonded to two electron-withdrawing carbonyl groups. The other carbonyl groups are bonded to one electron-withdrawing carbonyl group, and one electron-donating aromatic ring. The greater the number of electron-withdrawing groups, the less electron density surrounding the carbonyl C atom, and the more reactive this atom is toward nucleophilic addition. Practice Problem 3-11 Answer Within each set, which compound should be more reactive in carbonyl addition reactions? Explain your choices. Practice Problem 3-12 Answer Show how these four products can be synthesized from the same Grignard reagent. O O O Ninhydrin H 2 O acid or base O O OH OH The electron-withdrawing Br atom is closer to the carbonyl C atom. When less electron density is present on the carbonyl C atom, it is more reactive toward nucleophiles.
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