5.291 soare
5.294 roate
5.299 raise
5.311 raile
5.311 reast
5.321 slate
5.342 crate
5.342 salet
5.345 irate
5.346 trace
5.356 arise
5.360 orate
5.370 stare
5.382 carte
5.390 raine
5.400 caret
5.402 ariel
5.406 taler
5.406 carle
5.407 slane
Shown are the twenty best initial guesses using Claude Shannon's definition of information entropy. Each number is the expected number of yes/no questions needed to resolve the remaining uncertainty. Shannon is the "father of information theory", and this is the right measure.One might recognize SOARE as identified elsewhere by a different measure. I am relieved that I give up very little by moving down to the first word I recognize on this list.
This takes about 20 minutes to code in Ruby, and four minutes to run. There's no point to using a more efficient language, or wasting part of an hour as I did searching for a clever way to score guess words.
In the 1960's my dad used entropy to program Jotto on Kodak's computers. It wasn't feasible then to evaluate every possible clue word, but he determined that one did well enough with a random subset.