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a sling can throw a projectile up to 400 meters or further, in some cultures children grow up training with slings and in adulthood it develops into an extension of their arm, developing the ability to hit a target as small as a human head from a distance of 55 meters. To use a sling one only needs any plant fiber woven into a rope and a few rocks, cheapest weapon ever. Some sling throwers have shown the ability to throw rocks with the same force of a bullet, except it is a giant freaking bullet.

But here's the point, just like archery, to be good at throwing a slingshot it takes some years of practice while on contrary anyone can take up a musket and learn it in a few minutes, anyone can take a spear and follow shouted instructions or copy what the guys in the line around you do.

to make things easier, what about throwing dynamite with a sling? would it even explode or would the match lose fire mid air?

I also thought about oil bombs, they don't even need to hit the target, if it surrounds them, the fires and smokes are enough to suffocate or exhaust the enemy before they even get to melee. If it asphyxiates them, some enemy soldiers would get high before dying causing even more chaos.

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    $\begingroup$ Crossbows are the "traditional" ranged weapon to give the unskilled serfs you press into your army. They have been used since 650BC in China, it takes very little training to use one, and they can be made fairly cheaply (though obviously not as cheaply or quickly as a sling). Also consider javelins and other throwing spears (like the Roman pilum), which are just sharp sticks and also easy to learn to use, if hard to get pinpoint accuracy and with much shorter range. $\endgroup$
    – Taejang
    Jun 16 at 15:08
  • $\begingroup$ Explosives are dangerous, even for trained demolition teams. I wouldn't dare to give rookies a dynamite ready to blow x). On the other side, accuracy is important, but it's easily foreshadowed by the number of shots; Shooting with a bow at a roughly 45° angle towards the enemy is quite easy and enough for untrained troops, and was actually the way I handled a bow for the first time when I was a kiddy. $\endgroup$
    – Tortliena
    Jun 16 at 17:52
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    $\begingroup$ grenade slingers actually existed, they used lever type slings (staff slings) and fused grenades. note 400 meters is for a sling throwing a small stone not a large heavy explosive. $\endgroup$
    – John
    Jun 16 at 20:44
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    $\begingroup$ What exactly is your question here? Do you want to know if they could be done, if they would be practical if done, how they would compare to non-explosive slings, how they would compare to other artillery weapons, etc. $\endgroup$
    – Nosajimiki
    Jun 16 at 21:16
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    $\begingroup$ Also, there were no explosives in the ancient time period, so are we to assume you mean some time after ~1100CE or are you anachronistically adding explosives to point in the ancient world ~3000 BCE – 500CE? This would drastically affect what kinds of other weapons, armor, and fortifications you'd have to contend with. $\endgroup$
    – Nosajimiki
    Jun 16 at 21:49
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Viable but dangerous. If you mess up, you could fling an armed grenade at your own feet.

Lacrosse sticks (aka atlatls) are safer, as is tying a cord the grenade, spinning it around, and sending the grenade flying cord and all.

If you're using a burning fuse, you have to worry about igniting your sling. Solvable by soaking it in water.

All of which isn't to say slings have never been used.

https://history.stackexchange.com/questions/33103/were-slings-used-for-throwing-hand-grenades-if-not-why

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    $\begingroup$ What you're looking for is the staff sling instead of an Atlatl. A staff sling adds considerable velocity to a sling which an atlatl does the same to a throwing spear. $\endgroup$ Jun 16 at 11:00
  • $\begingroup$ For "cord around grenade, throw with cord and all" see "Bola". You might also want to look at the Xistera used in Jai Alai. en.wikipedia.org/wiki/Jai_alai $\endgroup$
    – PcMan
    Jun 16 at 14:14
  • $\begingroup$ This was also a plot point in one of Eric Flint's Belisarius SF alternate-history series of novels, so it's been used successfully in fiction before. His subordinates formed units of staff-sling grenadiers to counter an insurrection IIRC in the first novel. $\endgroup$ Jun 16 at 15:09
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You could use grenades with impact detonators, there were medieval black powder grenades which had a good chance of going off as they impacted the ground. They would also have a lesser chance of exploding whilst in the sling. I believe that timed fuses were more commonplace. (The fuse probably wouldn't go out but getting it to explode at the right moment is key - the burn time of primitive fuses may not be very predictable).

For something even less reliable how about something like an impact detonating molotov - which is just a glass bottle filled with flammable oil. The real molotov had reliable all way fuses but a medieval version might have a spark generator attached to it like a few pieces of flint which would have extremely hit-and-miss reliability (but if you were saturating an enemy position or building with these things then you would only need one spark to ignite the whole lot)

Or perhaps a two part explosive / reaction which could be delivered using two bottles or containers taped together. Depending on how good your alchemists are this could be a bomb or smoke bomb made with nitric acid and solvent, or some kind of chemical weapon like mustard gas.

None of the above would be particularly safe for the user but if the knowledge were readily available then they may at least be relatively easy to make. If you were at the level of industry where these kinds of explosives were becoming available, you might also be close to the point where some kind of cannon could be produced. But cannon might be prohibitively expensive - a few glass bottles and some bang juice is probably easier to rustle up than an iron cast or even a single use wooden barrelled cannon.

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If you have dynamite, then you either have, or are on the very cusp of discovering, gunpowder. So while, yes, you can sling dynamite (catapults and ballistae were used to lob grenades all the way up to World War I), the use-case for that capability is extremely short lived.

Your point about slings requiring skill is valid, but consider that: also like archery, slings were a common tool to obtain food, meaning that large portions of the population are versed in their use from a young age as a matter of practical tool training for civilian life. On top of this, skirmishing, which is what someone slinging explosives will be tasked with - the risk of friendly fire incidents is obscenely high otherwise - is a high-skill type of warfare already, so training/selecting for good sling/archery skills isn't as marginally costly as you might think.

The musket and it's brethren also only worked the way you describe when used in massed formations. An individual peasant musketeer couldn't hit the broadside of a barn except by luck - and that's only partially the fault of the musket. Proper sharpshooting took the gunpower boomstick and brought it straight into the same realm as archery and slings: a high-skill requirement to get the most out of the tool.

You can train slingers for a very short period of time and use them en masse to similar effect: quantity has a quality all its own.

Incendiaries are likely to be developed MUCH earlier than explosives, so a use case for "I want to set that person on fire, but I just can't reach" happens almost immediately after fire itself is discovered. Again, slings can do the job but the engineering requirements on the vessel are severe - it needs to resist the compression of the centrifugal force applied by the sling, and then break open on impact. On top of that, incendiaries (barring stuff like thermite or phosphorous), are best used in very large quantities: small fires are easy to put out and slow to spread. Large fires get out of control without any help at all.

If you've got powerful incendiaries like napalm, thermite, white phosphorous, or magnesium - which you might be able to discover/develop before explosives - now you're cooking with... liquid, I guess? As long as the vessel design can do what you need it to do, even something as simple as a strip of steel acting as a spring-arm (world's easiest catapult) will happily put that down range.

Long fuses that you hold onto to impart momentum to the bottle are likely better than slings because of the coordination required for proper sling use.

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