I've tried looking in other posts regarding my question, but couldn't find a definitive answer to my question.

• If a level 5 barbarian equipped with a 2-handed weapon attempts a grapple and succeeds, would the extra attack feature allow an attack with the 2-handed weapon?


• The barbarian's next turn comes around, can he still make 2 weapon attacks without breaking the grapple?

The rules for grappling states that the one who initiates the grappling needs at least one free hand, so it's been confusing for me...

No, you can not use a 2-handed weapon to attack when grappling*

As you've noted, when you grapple, you must be:

Using at least one free hand...

If the grapple is successful, that hand is now busy grappling. Unless you can wield the weapon in one hand (if it has Versatile property), then you do not have a weapon out that you can attack with.

You can still choose to use it as an improvised weapon, or you can use an unarmed strike if you have any remaining attacks left during the turn you used to grapple

Next turn, you are free to attack (but again, with only one arm)

If you are still maintaining your grapple (the target hasn't successfully broken it), then you use your attacks as normal. But you still only have one free hand available which limits your weapon options and prevents you from using your 2-handed weapon as above.

*unless you've got a third arm.

You can still attack, and use Extra Attack, but you can't use your 2-handed weapon to do it.

The Grapple Action specifies the following...

Using at least one free hand, you try to seize the target by making a grapple check instead of an attack roll [...] you can release the target whenever you like (no action required).

source

This pretty clearly states that you need at least 1 free hand to grapple your target, and that 'releasing them' ends the grapple. The problem comes that you're trying to use a two-handed weapon.

Two-Handed. This weapon requires two hands when you attack with it.

source

If you are Grappling a target, one of your hands is busy holding on to the person you have grappled. Therefore, you do not have two hands available to use a Two-handed weapon.

Work-arounds

If you are using a one-handed weapon, you can still hit them with that. You may also choose to use Unarmed Attacks instead. Note that you do not have to put your Axe down to do this, because...

Instead of using a weapon to make a melee weapon attack, you can use an unarmed strike: a punch, kick, head-butt, or similar forceful blow (none of which count as weapons). On a hit, an unarmed strike deals bludgeoning damage equal to 1 + your Strength modifier. You are proficient with your unarmed strikes.

source

So you could grapple someone then headbutt them into submission, without putting your axe down.