Possible blown head gasket or worse

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How white is the white in the valves? The pix is not close enough to see the color well, but if tannish, then it may just be normal burning. The white on the pistons is more indicative, IMO. I have taken off heads with a cylinder eating water via the gasket and seen no rust, so no rust in the bores not an indicator.....

Looks like the original type head gasket on there; it is the original type if it is a thin steel shim.

So there is no ring ridge near the top? It ought to be right where you can see the bore wear end. Check #1 especially closely.

The green staining on the springs does not make sense as coolant if you did not find any in the pan. Smell it and feel it to see if it is like A/F. Was it on all the valve springs? Anything coolant-wise on numerous springs has to come up from the oiling system or sprayed direct in the head from the water jacket. (Head crack) Look down in the lifter galleries (where the push rods go) and see if you see any there. (BTW, the lifter galleries look pretty clean.)

Any chance that the engine saw any freezing temps if your buddy put just water into it?

Looks to me like there is a gasket leak between cylinders 2&3 and perhaps 4&5, 1&2. Take a look there. If so, I'd take that as a good sign of head warpage. I'd have the head pressure checked for sure with the water leaks and who knows if only water was put in as coolant. If any cracks in the head, then there is a good chance of a block crack too.

See if you can borrow a precise straight edge and clean the deck and see if you can find warpage; it will be hard to find small warpage in-car on such a long block unless it is really bad but is worth a check IMO.
 
Yea it still had the steel shim gasket on it.

Yea I didn't feel any ring ridge at all...

No freezing temps. Cars been in Southern california.

He used a mix of coolant and water.

The valves look pretty white, I can take a better pic.
 
New exhaust valves, like $5 a piece. buy a 12" square granite tile from Home Depot and double side tape a piece of sandpaper to it. Mark your head surface and work the tile over the head in a 8 pattern. Youll soon see any low spots emerge as dark areas on an otherwise buffed surface. Time to deck it .090!
 
Sigh...what are you guys doing #-o

1. Stop guessing. Go take the head and have it checked at a reputable machine shop. They'll tell if it's cracked or needs surfacing. My opinion is it needs neither.

2. The white valves mean NOTHING. That's just how exhaust valves look when they operate because of the intense heat. It MIGHT be running a little lean but that's because of that admitted huge vacuum leak. Antifreeze stays on valves about 2/10's of a second, then the heat burns it away. You don't need valves because they are white, that's uninformed craziness. When the valve head has a chunk missing, or the head is busted off, yep you need a new valve then. Anyway, if the think was half-assed back together, with a four barrel for God's sakes....of course it's not going to run well.

3. When a head gasket blows there's lots of steam out the exhaust and it pushes water out the radiator. Saw no mention of those symptoms.

4. The 1/4 turns sounds like somebody tried to time it by "ear", meaning twisting the distributor one way or the other and got it out of time.

5. Your friend doesn't need to touch another tool or car part until he knows what he's doing. You aren't helping much by dissecting his engine as part of the guessing game.

6. I saw no mention of a compression test, vacuum gauge reading, valve adjustment or timing adjustment with a LIGHT. These are the basics any good mechanic performs on a poorly running engine FIRST. You don't start pulling heads off and looking for mystery patterns on the carbon on the valves. that's strictly amateur stuff.

I know I'm being hard on you but I ruined a couple engines back in the day screwing around. Have the head checked, put it back together PROPERLY and go from there. Otherwise, have your fun "analyzing" the engine, then get your friend into the nearest Cavalier he can find and don't EVER let him near another vintage Mopar.

Here is what your goal is:

[ame="https://www.youtube.com/watch?v=MKM0x7ujRwA"]Slant six purrs like a kitten - YouTube[/ame]
 
PS:

Engines START, RUN, STOP, STALL and QUIT.

Women turn ON and turn OFF, sometimes quickly.

That will help with your terminology:)
 
Kind of late for you, but for others. A poor man's compression test is simple and accurate. Turn the engine over by hand by tugging on the fan belt (easier access in early cars). If you must stop and wait 5 sec for each cylinder to hiss down - i.e. fight 3 strong "air springs" per rev, you know all cylinders are good and the engine is like new. If they bleed down faster, the engine could still be OK, but you need to spin it with the starter and use a compression gage to tell.

It is hard to warp a cast-iron head. You can find idiots purposely trying to destroy slant six engines on youtube, and it isn't easy. They can run at high rev for 20 minutes w/ no coolant before the bearings finally overheat. I won't fault your friend for trying. The only way to learn is to screw up. The important thing is that he does learn and not just whine on you. One lesson is to read a manual and search sites like here for info instead of just guessing "maybe this goes here". Leaving off manifold gaskets and hooking the throttle cable to the choke shows no attempt at research.

Re what a well-running slant should sound like, it depends on the setup. Post 29 sounds great for a factory setup. Post 31 is more typical for a wilder camshaft and custom exhaust. My 64 Valiant 225 is so quiet at idle that when it died driving it home (bad ignition circuit and charging), I once hit the starter while the engine was already running. It was so quiet and smooth, I couldn't tell it was running above background traffic. I think the factory air cleaner has a lot to do with that (thin entrance gap around bottom). I later adjusted the valves and they were spot on, so don't expect your should hear much ticking. My 69 Dart 225 used to shake a bit at idle and liked to die when accelerating (idling lean). With the 4th Holley 1920, it purred like a kitten and jumped off the line. Most of the crappy idling was probably vacuum leaks (no gasket does that).
 
Alright well just to update everything...

Took the head to the machine shop.

IN fact blown head gasket. Machinist also said head was warped.

Tested the valves and said they're working fine.
Checked for cracks said there's no cracks.

So he resurfaced the head and told me it was good to go, everything checked out fine.

So next I will put it back together.

Thanks for everyone's input.

I'll post a video of it running when I can.
 
Obviously got too hot with no coolant.....

Hopefully the block is not warped also; it can happen. Hopefully not. At this point, use a composite gasket like Felpro, and be sure to torque per the manual and re-torque after a couple of short heat cycles. Watch for brown foamy stuff in the oil. Use green antifreeze like Prestone and resist the temptation to put in just water at first; with green A/F, you can spot any greenish content in the oil. Do your buddy a favor and just spend the few extra $$ for some anti-freeze even if you are in SoCal; these engines will rust up and scale up on the inside like any other and have cooling issues, and it does not sound like you buddy would bother to change it later. One gallon is all you need for those temps and you will get the anti-rust/anti-corrosion agents needed.

Flush the radiator before you fill up the engine with coolant.
 
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