$re = '/(?im)^(?!$)(?:(Question|Problem:?|Example|[A-Z])[. ]?)?(\d+[. ]?)?(?=\s)/m';
$str = 'Q 12. This is question 1
Example 1 This is question 2 Q.1
Example This is question 3
EXAMPLE 2 This is question 4 2.3
Q.12. This is question 5
5.
Q 55.
Q 555
Q.555.
55555
Question 5555
Example
Problem 5555
Problem:
A5555.
EXAMPLE
Example 5555555';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php