It is possible, but hopefully not the case, that you accidentally discarded the hexyl acetate layer and tried to distill the other product of the reaction, water! If you were using a fractional distillation setup and the upper part of the fractionating column was not able to heat up sufficiently during the distillation, the liquid would boil but just reflux for a long time without actually distilling over. If it was water, you could get the kind of behavior you observed. The temperature would never go over 100° and it could fluctuate if drafts of air in the room intermittently cooled the fractionating column which would affect how much vapor was contacting the thermometer. After the reaction between acetic acid and hexyl alcohol is complete, you would have two liquid layers remaining, a lower water layer and an upper hexyl acetate layer, since hexyl acetate is insoluble in water and less dense. But it depends on how you do the reaction. Since in this reaction water is the lowest boiling component, it could be removed by distillation as it forms during the reaction, leaving the higher boiling substances behind. At the end of the reaction you would have mainly just the ester product remaining in the original reaction vessel. But on the other hand if you did the reaction in a reflux setup, you would have the two product layers after the reaction was complete and ideally little or no unreacted acetic acid and hexyl alcohol remaining. So however you did the reaction, if you're sure you saved the correct layer for distillation, it was a bad hot plate. Otherwise....ooops! Believe me, it happens! Steve
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