Re: Regex word options

Not exactly as you stated the problem, but an extensible approach:

C:\>perl -E "my @work=(\"I Arranged a meet.\", \"Transcribe this\"); 
for $work(@work) { 
    if ($work =~ /Transcribe||Arranged/) {
        say $work; 
    } 
}

I Arranged a meet.
Transcribe this

C:\>
[download]

The \b does nothing useful as you state your problem; alternation is better done with an ||, ("or"). Solving the captures as you need them is left as an exercise.

In Section Seekers of Perl Wisdom