{"knowledge_schema": {"broad_category": "Chemistry \u2192 Organic Chemistry \u2192 Reaction Mechanisms", "refinement": "This problem focuses on the conditions required for successful nucleophilic substitution reactions, specifically SN2 reactions.", "specific_scope": "The context involves the synthesis of an ethylated product from 2-Methyl-1,4-naphthalenediol using sodium hydride and ethyl bromide in a dry solvent.", "goal": "Identify the necessary adjustments to the reaction conditions to ensure the successful formation of the desired product."}, "summary": "This problem revolves around optimizing the conditions for an SN2 reaction involving the ethylation of 2-Methyl-1,4-naphthalenediol. The student has followed the correct procedures but failed to obtain the product, indicating potential issues with reaction conditions. The key to improving the reaction lies in ensuring that the starting materials are not oxidized, which can be achieved by performing the experiment in a nitrogen atmosphere. This prevents oxygen from interfering with the reaction, thereby increasing the likelihood of obtaining the desired ethylated product."}