Terry J. Reedy added the comment:

When encountering a bug, it helps to determine the minimum needed to invoke the 
bug.  os.chdir is irrelevant and distracting noise as far as investigating 
these bugs.  There turns out to be two.  Raw versus cooked mode is also 
irrelevant, so an 'r' prefix is not needed.  The path separator also seems to 
not matter.  So we can use '/'.

I did several tests with 3.6 on Windows 10, first in Shell, then a quick 
confirmation in a fresh editor.  What does matter is the open quote: ', ", ''', 
or """. When one types a string without completions, the opening quote along 
with any prefix is colored, as is the subsequent content and closing quote as 
they are entered.  This should remain true when completions are involved.  It 
is true for opening """ or ".  For ''' and ', the first action after typing '/' 
is colored, subsequent actions are not. The action can be either typing a 
letter or moving the selection in the completion box with up or down arrow.  
(Things are different when moving around in a string and forcing completions 
open with cntl-space.)

When one types a closing quote, the final directory should be completed if it 
is not already and the completion box closed.  This is true for """ and ", but 
''' and ' neither complete nor close.  After a ''', additional characters are 
also colored.  For "'''/Ga'''me", the "me" are also, improperly, colored and 
the box remains.

We thus have two bugs: a color but that depends on the number of open quotes 
and a complete and close bug that depends of the type of open quote.  A single 
single quote has both.  Thank you for the report.

Colorizer has a pair of symmetrical regexes for single quote strings (possible 
not complete) and another pair for triple quote strings.  (Symmetrical means 
identical except for reversing roles of ' and ".)  So it is plausible that 
these might be the cause of a number-dependent bug.  It has a debug most that 
could be turned on doing file completion in an editor.

----------
stage:  -> test needed
title: IDLE does not fully color raw string directory paths to green when 
invoking os.chdir() if statement is executed with autocompletion drop down list 
still open -> IDLE file completion has 2 bugs depending on open quote used
versions: +Python 3.6 -Python 3.5

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<http://bugs.python.org/issue27675>
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