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The candidate words and Plonk’s answers have been chosen to allow the answer to be deduced by analysis. But programatically a brute force approach does just as good a job in 39ms.

Solution:The letter Plonk chose is ‘H’.Analytically we can consider the problem like this:

If we consider the six candidate words in pairs, and equate them by their letter content we see:

CARTHORSE = ORCHESTRA

SENATORIAL = REALISATION

INDETERMINABLES + H = ANTIDISESTABLISHMENTARIANISM

And for each pair Plonk gave both a “Yes” and a “No” answer.

Which means if his letter was any letter other than H he has answered exactly three of these six questions correctly. However this situation is precluded by the first question, where he states he will answer exactly three questions correctly. This statement cannot be either true or false.

Hence the letter chosen is H, and Plonk answers four of the last six questions correctly, and the the answer to the first question is incorrect.