Combining Entangle with Web

[Atalius]

My ally is an alchemist and liberally uses Tanglefoot bombs. My question is if he uses a bomb on a group of say 5 enemies and I use Web after him and all the enemies fail there saving throws what happens? What is the end result?

[John Murdock]

tanglefoot bombs cause the condition entangled who does that

''An entangled creature moves at half speed, cannot run or charge, and takes a –2 penalty on all attack rolls and a –4 penalty to Dexterity. An entangled character who attempts to cast a spell must make a concentration check (DC 15 + spell level) or lose the spell.''

and web spell say this

''Creatures caught within a web become grappled by the sticky fibers. Attacking a creature in a web doesn’t cause you to become grappled.''

so they are grapple and you can attack them without being grapple and grapple does the following

''Grappled creatures cannot move and take a –4 penalty to Dexterity. A grappled creature takes a –2 penalty on all attack rolls and combat maneuver checks, except those made to grapple or escape a grapple. In addition, grappled creatures can take no action that requires two hands to perform. A grappled character who attempts to cast a spell or use a spell-like ability must make a concentration check (DC 10 + grappler’s CMB + spell level), or lose the spell. Grappled creatures cannot make attacks of opportunity.''

and the web also create difficult terrain and if you are at least 5 foot of the web both of you have cover (+4 to AC +2 to reflex save) and if you are at least 20 feet it provide to both of you total cover.

so in all the enemies would have a -4 penalty to attack roll and -8 penalty to dexterity, which mean an effective -4 to AC and another -4 to attack if they use weapon finesse or any attack that rely on DEX, add to that they can't make an AoO and can't move, and having 2 concentration check for caster.

the only downside is the cover or total cover if you are far enough, which mean this combo is very ideal to help melee attacker in the group but is an hindrance to ranged attacker in the group

[Atalius]

When they try to escape do they escape the condition that was thrown at them first (which is a standard action) and then the following round break free of the other condition?

[Ridiculon]

its their choice as to which condition they deal with first

[John Murdock]

depending of how to remove the condition, they need to make a roll and the action demanded with the DC that the thing inflicting the condition demand if both demand a standard action you need in total 2 roll, but if one say that if you remain you must make a save or else you return to the condition it is best to remove the second condition before the first to evade the scenario that you have to remake another roll to evade the first one again