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I’m tutoring ochem this summer, and my students had a question from the professor about ranking the acidity of various compounds. Most were easy enough, but they were confused about whether 2-chloropentanoic acid or 3-fluoropentanoic acid was more acidic. Their professor said 3-fluoro was more acidic, and they asked me why, and I didn’t really have a good answer. I told them it’s because fluorine is so electronegative that even 2 positions away, the inductive effect still makes it a stronger acid than chlorine. But the truth is, if I had been answering the question, I probably would have said that 2-chloropentanoic acid is the most acidic, because I was always taught that distance is the most important factor with the inductive effect. Is the professor right? I was trying to find pKa values online to answer for myself but couldn’t find any. And what’s the best way to approach these ranking questions where the acids differ in both EWG and position of EWG?

Basic physics. Work/energy and force are different fundamental physical concepts. Knowing the force at _some_ point of the bond breaking process is not enough to say how much work needs to be done to achieve separation.

Please read the forum rules; you have to show an attempt of your own before receiving help.

In any case, I don't know what a lambda factor is, I don't know what the selected equilibrium reaction is, and I don't have the basic thermodynamic information to hand. Is this information that is provided in the question paper but you are withholding from us? How do you expect anyone to solve this problem?

Hello everyone,
I am posting this message because I have an exercise to do and I am completely lost. Could you help me on how to do it? :

Exercise:
Consider the combustion of methane with regular air. Inlet temperatures of methane and air are 300 K and 400 K, respectively. The mass flow rate of air is 0.1 kg/s, and the lambda factor is 0.9.
This is a case of a rich mixture (λ<1). In this case, the species in the products will contain CO2, H2O, CO, H2, and N2, among other species. Mass (or atoms) conservation is not enough to close the problem.

1) Considering only the five species in the products mentioned above, evaluate the Kp of the selected equilibrium reaction based on the basic thermodynamic information (enthalpies of formation, molar heats and reference entropy of the species involved).

2) Evaluate the concentration of the five species considering Tcc=1400 K

3) Evaluate the combustion temperature and the concentration of the five species (global itetaive process)

Thank you for your help. This exercise is very important to me.