<?xml version="1.0" ?>
<beilsteinTutorial creator="kosatab@vscht.cz">
<key>melting point</key>
<key>by-product</key>
<description>You treated naphtalene-1,6-diol with acetyl chloride, and you obtained two products. One of them was a product of acetylation in position 2. The second product is crystalic, with mp=106-107. What is it?</description>
<query>
<comment>This question is rather difficult. Firstly we try to find these reactions of naphtalene-1,6-diol where reagent is acetylchloride.</comment>
<subquery hits="54" pict="ex40a">the reactions of diol</subquery>
<subquery hits="2839" text='(rx.rgt=accl or rx.rgt="acetyl chloride")'>then acetyl chloride as the reagent</subquery>
<subquery text=".Q1 or.Q2" hits="0">finally, we put them together. Whooops, nothing found</subquery>
</query>
<query>
<comment>We can try reactions of diol that leads to product with mp=100-110 (we can't be sure of exact mp=106-107)</comment>
<subquery hits="54" pict="ex40a">diol first</subquery>
<subquery text="mp=100-110" hits="258838">all compounds with desired melting point</subquery>
<subquery text=".Q1 and.Q2" hits="4">put them both together</subquery>
<hit brn="387787" class="extra"></hit>
<hit brn="2276905" class="extra"></hit>
<hit brn="7762777" class="hit">and this is the one we searched for</hit>
</query>
</beilsteinTutorial>