Capacitor in series circuit

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I was doing the diode clamping experiment and got in over my head so I removed the diode to make things simpler

This is what I had

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Vin and Vout are almost in phase

When I connect the signal generator to the input I clearly observe Vout swinging from positive to negative ad infinitum both on a scope and multimeter

In an attempt to observe each sequence individually I input positive DC to Vin

But get nothing for Vout

I know yeah capacitors block DC but trying to figure out how AC can influence Vout but not DC

 

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I had hit a brick 🧱 wall with this and needed some ideas so I tried it without the resistor just an open circuit

When I input DC now it's reflected on the other side of the capacitor

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Essentially Vin now equals Vout

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That said I bet now if I close the circuit that one side of the capacitor will discharge and be at zero

So I'm guessing my frustration at not being able to see isolated iterations of each sequence of the AC input circuit is because when I simply add DC and hold it there the other side discharges
Whereas input AC it's changing before the other side can react

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I flipped the power supply leads and the capacitor terminals to obtain the coveted negative DC 

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I have to remind myself that this stuff is not gonna do what I want it to do

Anyhow moving forward now maybe I can try to figure out a combination capacitor and resistor combination that would take the longest to discharge

Or a combo where I can input DC on one side and see it on the other side then slowly dissapate