In general, you cannot cast more than one spell with a single click of a macro. Most spells and some items trigger the global cooldown (GCD) which keeps you from taking too many actions at once. Even if a spell fails to cast, if it would trigger the GCD, it prevents subsequent /casts in the macro from running. This was not the case prior to patch 2.0 which is why you may still come across macros like the following:
/cast Overpower
/cast Execute
/cast Mortal Strike
/cast Sunder Armor
Macros like this do not work anymore.
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