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We introduce a method to generate candidate pairs of related Italian words sharing (or not) synonymous relations from the ConceptNet knowledgebase. The pairs are intended to generate questions for a vocabulary trainer which combines exercises to enhance vocabulary skills with the implicit crowdsourcing of linguistic knowledge about the semantic relations between words. Our method relies on the idea that pairs of synonyms in a language tend to translate to pairs of synonyms in other languages. We generated 85k candidate pairs of Italian synonyms that can be used to produce questions for both teaching (3.8 k pairs) and crowdsourcing purposes (80k pairs). Follow-up efforts are however needed in order to generate a complementary set of questions.