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Syntactic REAP.PT: Exercises on Clitic Pronouning Freitas, Tiago Baptista, Jorge Mamede, Nuno Intelligent Computer Assisted Language Learning (ICALL) Portuguese Syntactic Exercises Automatic Exercise Generation Clitic Pronouning The emerging interdisciplinary field of Intelligent Computer Assisted Language Learning (ICALL) aims to integrate the knowledge from computational linguistics into computer-assisted language learning (CALL). REAP.PT is a project emerging from this new field, aiming to teach Portuguese in an innovative and appealing way, and adapted to each student. In this paper, we present a new improvement of the REAP.PT system, consisting in developing new, automatically generated, syntactic exercises. These exercises deal with the complex phenomenon of pronominalization, that is, the substitution of a syntactic constituent with an adequate pronominal form. Though the transformation may seem simple, it involves complex lexical, syntactical and semantic constraints. The issues on pronominalization in Portuguese make it a particularly difficult aspect of language learning for non-native speakers. On the other hand, even native speakers can often be uncertain about the correct clitic positioning, due to the complexity and interaction of competing factors governing this phenomenon. A new architecture for automatic syntactic exercise generation is proposed. It proved invaluable in easing the development of this complex exercise, and is expected to make a relevant step forward in the development of future syntactic exercises, with the potential of becoming a syntactic exercise generation framework. A pioneer feedback system with detailed and automatically generated explanations for each answer is also presented, improving the learning experience, as stated in user comments. The expert evaluation and crowd-sourced testing positive results demonstrated the validity of the present approach. Schloss Dagstuhl – Leibniz-Zentrum für Informatik Tiago Freitas and Jorge Baptista and Nuno Mamede 2013 Is Part Of OASIcs, Volume 29, 2nd Symposium on Languages, Applications and Technologies (2013) InProceedings Text doc-type:ResearchArticle publishedVersion application/pdf doi:10.4230/OASIcs.SLATE.2013.271 urn:nbn:de:0030-drops-40433 https://drops.dagstuhl.de/entities/document/10.4230/OASIcs.SLATE.2013.271 eng https://creativecommons.org/licenses/by/3.0/legalcode