Acetoacetate could form a hydrogen bond with another acetoacetate molecule.

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Question restatement: The statement is asking whether acetoacetate could form a hydrogen bond with another acetoacetate molecule.
Option 1: True. This is the correct viable possibility. Acetoacetate contains functional groups capable of participating in hydrogen bonding: the carbonyl oxygen can act as a hydrogen-bond acceptor, and in the enolizable beta-dicarbonyl system there is potential for an enol form that bears an -OH group, which can donate a hydrogen bond. As a result, two acetoacetate molecules can interact via intermolecular hydrogen bonding, for example with the enol -OH donating to a carbonyl oxygen of the neighboring molecule, or carbonyl oxygens accepting H-bonds from any available proton donors. This kind of association is common for beta-dicarbonyl compounds and is observed in solution and crystal structures as dimers or aggregates.
Option 2: False. This would claim that acetoacetate cannot engage in hydrogen bonding with another molecule, which contradicts the presence of a carbonyl group that serves as an H-bond acceptor and, under tautomeric/enolizable conditions, an -OH donor as well. This option ignores well-established hydrogen-bonding capabilities of beta-dicarbonyl compounds and the enol/keto tautomerism that enables donor sites, making it an inaccurate statement.
In summary, the chemical features of acetoacetate support intermolecular hydrogen bonding, so the statement asserted by the question aligns with known behavior of such molecules, while the alternative would not align with the structural realities.

251A-LIFESCI-7A-LEC-1 AoL 1 - Group Phase Makeup

Acetoacetate could form a hydrogen bond with another acetoacetate molecule.

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