The language lawyer answer is (I believe) to be found in §6.5.8.5 of the C99 standard (or more precisely from ISO/IEC 9899:TC3 Committee Draft — Septermber 7, 2007 WG14/N1256 which is nearly identical but I don't have the original to hand) which has the following with regard to relational operators (i.e. <, <=, >, >=):
When two pointers are compared, the result depends on the relative locations in the address space of the objects pointed to. If two pointers to object or incomplete types both point to the same object, or both point one past the last element of the same array object, they compare equal. If the objects pointed to are members of the same aggregate object, pointers to structure members declared later compare greater than pointers to members declared earlier in the structure, and pointers to array elements with larger subscript values compare greater than pointers to elements of the same array with lower subscript values. All pointers to members of the same union object compare equal. If the expression P points to an element of an array object and the expression Q points to the last element of the same array object, the pointer expression Q+1 compares greater than P. In all other cases, the behavior is undefined.
(the C11 text is identical or near identical)
This at first seems unhelpful, or at least suggests the that the implementations each exploit undefined behaviour. I think, however, you can either rationalise the behaviour or use a work around.
The C pointers specified are either going to be NULL, or derived from taking the address of an object with &, or by pointer arithmetic, or by the result of some function. In the case concerned, they are derived by the result of the sbrk or mmap system calls. What do these systems calls really return? At a register level, they return an integer with the size uintptr_t (or intptr_t). It is in fact the system call interface which is casting them to a pointer. As we know casts between pointers and uintptr_t (or intptr_t) are by definition of the type bijective, we know we could cast the pointers to uintptr_t (for instance) and compare them, which will impose a well order relation on the pointers. The wikipedia link gives more information, but this will in essence ensure that every comparison is well defined as well as other useful properties such as a<b and b<c implies a<c. (I also can't choose an entirely arbitrary order as it would need to satisfy the other requirements of C99 §6.5.8.5 which pretty much leaves me with intptr_t and uintptr_t as candidates.)
We can exploit this to and write the (arguably better):
if ((uintptr_t)start_object <= (uintptr_t)my_pointer && (uintptr_t)my_pointer < (uintptr_t)(end_object+1)) {
There is a nit here. You'll note I casted to uintptr_t and not intptr_t. Why was that the right choice? In fact why did I not choose a rather bizarre ordering such as reversing the bits and comparing? The assumption here is that I'm chosing the same ordering as the kernel, specifically that my definition of < (given by the ordering) is such that the start and end of any allocated memory block will always be such that start < end. On all modern platforms I know, there is no 'wrap around' (e.g. the kernel will not allocate 32 bit memory starting at 0xffff8000 and ending at 0x00007ffff) - though note that similar wrap around has been exploited in the past.
The C standard specifies that pointer comparisons give undefined results under many circumstances. However, here you are building your own pointers out of integers returned by system calls. You can therefore either compare the integers, or compare the the pointers by casting them back to integers (exploiting the bijective nature of the cast). If you merely compare the pointers, you rely on the C compiler's implementation of pointer comparison being sane, which it almost certainly is, but is not guaranteed.
Are the possibilities I mention so obscure that they can be discounted? Nope, let's find a platform example where they might be important: 8086. It's possible to imagine an 8086 compilation model where every pointer is a 'far' pointer (i.e. contains a segment register). Pointer comparison could do a < or > on the segment register and only if they are equal do a < or > onto the offset. This would be entirely legitimate so long as all the structures in C99 §6.5.8.5 are in the same segment. But it won't work as one might expect between segments as 1000:1234 (which is equal to 1010:1134 in memory address) will appear smaller than 1010:0123. mmap here might well return results in different segments. Similarly one could think of another memory model where the segment register is actually a selector, and a pointer comparison uses a processor comparison instruction was used to compare memory addresses which aborts if an invalid selector or an offset outside a segment is used.
You ask two specific questions:
Whether or not comparing pointers from different calls to sbrk may be optimised away, and
If so, what glibc does that lets them get away with it.
In the formulation given above where start_object etc. are actually void *, then the calculation may be optimized away (i.e. might do what you want) but is not guaranteed to do so as the behaviour is undefined. A cast would guarantee that it does so provided the kernel uses the same well ordering as implied by the cast.
In answer to the second question, glibc is relying on a behaviour of the C compiler which is technically not required, but is very likely (per the above).
Note also (at least in the K&R in front of me) that the line you quote doesn't exist in the code. The caveat is in relation to the comparison of header * pointers with < (as I far as I can see comparison of void * pointers with < is always UB) which may derive from separate sbrk() calls.
