Motivated by the construction of free quandles and Dehn quandles of orientable surfaces, we introduce Dehn quandles of groups with respect to their subsets. As a characterisation, we prove that Dehn quandles are precisely those quandles which embed naturally into their enveloping groups. We prove that the enveloping group of the Dehn quandle of a given group with respect to its generating set is a central extension of that group, and that enveloping groups of Dehn quandles of Artin groups and link groups with respect to their standard generating sets are the groups themselves. We discuss orderability of Dehn quandles and prove that free involutory quandles are left orderable whereas certain generalised Alexander quandles are bi-orderable. Specialising to surfaces, we give generating sets for Dehn quandles of mapping class groups of orientable surfaces with punctures and compute their automorphism groups. As applications, we recover a result of Niebrzydowski and Przytycki proving that the knot quandle of the trefoil knot is isomorphic to the Dehn quandle of the torus and also extend a result of Yetter on epimorphisms of Dehn quandles of orientable surfaces onto certain involutory homological quandles. Finally, we show that involutory quotients of Dehn quandles of closed orientable surfaces of genus less than four are finite.
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