The goal of Korean education is smooth communication. Therefore, it is more than necessary to disclose the constraints and define semantic functions clearly when learning grammar, which is its goal. Also, restricting pragmatic and narrative situations and determining which situations such grammar is generally used and how it is different from similar grammar would also be the most effective way to reduce errors and carry successful communication. In addition, using proper grammar that corresponds to speaker’s intention would enhance expression and help improve listener’s understanding. Based on such perspective, this study focused on ‘-(으)ㄴ/는 한’, which connects two propositions as a condition and result. ‘-(으)ㄴ/는 한’ can’t be properly explained just with the combination of compositions, so it needs to be understood as one sentence structure and examined for its syntactic and semantic functions. In Korean education, ‘-(으)ㄴ/는 한’ was rarely focused on, either in the grammar study that describes about the condition or the bound noun phrase study. However, not only it is frequently used and discussed frequently in bound nound phrase studies, it is frequently used as a question in Korean proficiency test that studies on ‘-(으)ㄴ/는 한’ would be essential. Through the comparison with conditional connective ending ‘-으면’, this study determined that ‘-(으)ㄴ/는 한’ is usually used to express what is already realized or speaker’s firm belief that it will be realized when examining the semantic function, and has a pragmatic characteristic that expresses limited condition. Also, in terms of syntactic restriction relationship, it can be combined with state verb under certain conditions, unlike what is suggested in Korean textbooks, and the study also examined about restrictions in tense morpheme combination, characteristics in following clause mood and restrictions in semantic marker combination. Lastly, it suggested uses among various uses of ‘- 으면’ that can’t be substituted with ‘-(으)ㄴ/는 한’.