.. or .. which ... - does the which apply to both options?
Hi I'm not sure of the exact meaning of this sentence:
You may not engage in private practice or be connected with any outside business which would interfere with the performance of official duties.
Can I read this as meaning I CAN engage in private practice provided it DOES NOT interfere with the performance of official duties.?
As in You may not (engage in private practice OR be connected with any outside business) which would interfere with the performance of official duties.
The sentence in question—
You may not engage in private practice or be connected with any outside business which would interfere with the performance of official duties.
—has two levels of ambiguity:
Does "which would interfere with the performance of official duties" apply both to "You may not engage in private practice" and to "[You may not] be connected with any outside business," or does it apply only to "[You may not] be connected with any outside business"?
Does "which would interfere with the performance of official duties" apply restrictively or nonrestrictively to the antecedent or antecedents that it applies to?
As these two questions suggest, four more-or-less defensible readings of the original sentence are possible:
Reading 1: The "which" clause is restrictive and applies to both antecedents.
Reading 2: The "which" clause is restrictive and applies only to the second antecedent.
Reading 3: The "which" clause is nonrestrictive and applies to both antecedents.
Reading 4: The "which" clause is nonrestrictive and applies only to the second antecedent.
Now let's consider how we might alter the original sentence in order to convey, unambiguously and in turn, each of the four possible meanings outlined above. Using U.S. punctuation and style conventions, we might accomplish that goal as follows:
Reading 1: "You may not engage in private practice if doing so would interfere with the performance of official duties, and you may not be connected with any outside business if maintaining such a connection would interfere with the performance of official duties."
Reading 2: "You may not engage in private practice, and you may not be connected with any outside business that would interfere with the performance of official duties."
Reading 3: "You may neither engage in private practice nor be connected with any outside business, because either action would interfere with the performance of official duties."
Reading 4: "You may not engage in private practice; and furthermore, you may not be connected with any outside business, because the latter arrangement would interfere with the performance of official duties."
As you can see, the original sentence doesn't look terribly similar to any of those four formulations. That is because it—unlike them—is arguably ambiguous (arguably by a competent and dedicated lawyer, that is). It simply isn't beyond question that the writer of the sentence intended "which would interfere with the performance of official duties" to apply only to the second antecedent clause, nor is it beyond question that the "which is intended restrictively rather than nonrestrictively. The stage is set for multiple rounds of "the lawyers win and all their clients lose."
From his comments in the posted question, I gather that the OP would like to interpret the original sentence in accordance with Reading 1. A lawyer could certainly make such a case—but in my view the least tortured interpretation of the original wording favors what I have called Reading 2, which amounts to saying the following:
You may not (1) engage in private practice or (2) be connected with any outside business that would interfere with the performance of official duties.
This reading does little violence to the original wording (beyond replacing which with that, and inserting parenthetical numbers to fully separate the two prohibitions that the sentence seeks to impose), and it interprets that wording unambiguously and in good faith. But I made that assessment as a reader trying to make sense of an imperfectly framed statement, not as a lawyer trying to win a case for my client. In the adversary system of law, what matters most to an advocate isn't which interpretation is most reasonable, but rather which argument gives one's client the best prospect of persuading the jury (or judge).