Classically, the dynamics of the chiral oscillator (CO) may be described by the Landau model (LM) through a well established mathematical procedure known as duality mapping. In this letter we show how this duality is broken in quantum mechanics due to the presence of a Z2-anomaly in the CO. We give the theoretical basis for an experimental setup displaying the possibility to measure this global anomaly using cold Rydberg atoms.Duality is a mapping between two different mathematical descriptions of a same physical phenomenon. A strongly (weakly) coupled theory is mapped, through duality, in a weakly (strongly) coupled theory. Therefore, dualities have a striking importance in the study of strongly interacting models. Examples in condensed matter and high energy physics are the Kramers-Wanier high/low temperature mapping, the 4D electromagnetic Montonen-Olive particle/soliton conjecture and the string dualities [1]. All these examples involve theories with many degrees of freedom but of course this is not a necessary condition.In this work we study duality in an example involving finite degrees of freedom, the LM/CO duality. Both models describe the classical trajectories of a particle in the x-y plane subject to a constant magnetic field B = B z [2, 3, 4], and therefore, the classical duality would be already expected. The issue of duality at the quantum level is however more subtle. It was shown in [3,5] that the CO has a Z 2 -anomaly that forces its orbital angular momentum to be quantized in half-integer units ofh, either positive or negative, letting it with an uncommon behavior through rotations. This anomaly has a great resemblance with the Z 2 -anomaly of a single Weyl fermion coupled to a SU(2) Yang-Mills field discovered by Witten [6]. We show in this Letter that, at the quantum domain, the partition function for the LM can be factorized as the product of two Z 2 -anomalous theories -the CO and a "mechanical Chern-Simons (CS)" model. We discuss how the CO and the LM differently respond to this anomaly and how this process is related with the violation of duality in quantum mechanics. We also discuss the theoretical basis for an interferometer experiment, involving cold Rydberg atoms pointing, at least in principle, a possible direction leading to direct consequence of the Z 2 anomaly -the gain of a π phase factor by the CO fundamental state -with consequences to the existence (or not) of the quantum duality. Now, we analyze the LM/CO duality in a classical and quantum context. The Lagrangian of the LM can be written aswhere ǫ ij is the Levi-Civita symbol. The CO model, on the other hand, is given bywhere we consider g and k > 0. These models describe a particle in an uniform circular motion with the frequency ω LM = g m and ω CO = k g . A necessary condition to the LM/CO duality is to set g 2 = km so ω LM = ω CO = ω.As usual, duality means that both models predict the same effects in an indistinguishable form, i.e., there is no possibility of discriminating them by means of any kind of experiment. In the...