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I prefer to proceed with a concrete example if I may. I appreciate that the answer might well be better explained with group theory, geometry and/or notions from probability theory, which I welcome.

Let $\{x\}$ denote the fractional part of $x$, $(p,q)=1$ and $p\leq q$. If $n\in\mathbb{Z}_q$, then the set of $\phi(q)$ functions defined by

$$f_p(n)=q\{pn/q\}$$

form the complete set of automorphisms of $\mathbb{Z}_q$.

As we vary $p$ through $\mathbb{Z}_q^{\times}$, it is not apparent to me that there is prescribed order in which the elements of $\mathbb{Z}_q$ reappear, neither do I see a rule not involving the function $\{x\}$.

Say we choose some large $q$, then is it the case that order in which the elements reappear exhibits some sense of randomness, and in what sense if so?

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    $\begingroup$ Your map f_p is just multiplication by p in the ring of integers mod q. As p runs over the units in this ring, it is well known that this gives all of the automorphisms of the additive group of the ring. I guess I don't see why there is any randomness here. $\endgroup$ Commented Jul 24, 2014 at 23:09

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It appears that this is equivalent to the question of the complexity of the discrete logarithm problem, so I think this question is in general an open problem and ought to be retagged and treated as such.

As Maarty Isaacs commented $$f_p(n)=np\mod q.$$ To say that the order in which the elements reappear is of a random nature is to say that $np\mod q$ is of high complexity, which is the same as the complexity of its inverse.

In other words, given a cyclic group $G$, a generator $g$ and an element $f$, the question is:

How difficult is it to find an integer $n$ such that $f=g^n$?

EDIT: This is not correct. Firstly, the complexity of the inverse (i.e. the discrete logarithm problem) is not necessarily the same. In fact, from what I can gather, this is part of the reason why discrete logs are useful in cryptography at present. Secondly, when the modulus is large (compared to $p$), one gets a string of arithmetic progressions that eventually include the whole set, which is rather predictable. So the only case that may still work is when the modulus is small, but frankly this doesn't look very interesting either!

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  • $\begingroup$ It's certainly not random, but I don't know if I agree with the last assessment; I find it quite interesting. There's actually a rather deep recursive structure in the order of the coefficients that's related to the continued-fraction expansion of $\frac pq$ (the best references I know of for this behavior come from discussions of Bresenham's line-drawing algorithm, but that may just be because it's how I was originally introduced to the topic). $\endgroup$ Commented Aug 27, 2014 at 18:36

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