A flask containing acetone accidently had a small sample of a concentrated aqueo

Question

A flask containing acetone accidently had a small sample of a concentrated aqueous solution of potassium hydroxide added to it.   The flask became quite warm and somewhat dark yellow-brown in color. After the initial exothermic reaction, the laboratory worker decided to try to identify the contents of the flask and see if any acetone could be recovered. To separate the acetone and products the researcher flash-distilled all volatiles from the crude mixture under high vacuum (0.1 mm Hg) into a receiver flask cooled with liquid nitrogen. The residue in the distillation was black in color and extremely caustic (basic). The collected volatiles were essentially colorless and smelled of acetone with some other odors unknown to the researcher apparently also present. The volatiles were again subjected to distillation with the intent to fractionate the components. At atmospheric pressure, a 200 mL sample of the volatiles were heated to distill 53 mL of a liquid boiling at 57 degrees C which proved to be acetone. On further heating, 27 mL of a liquid boiling at 100 degrees C was collected. No further distillate was collected at atmospheric pressure. The still pressure was reduced to 50 mm Hg and 51 mL of a colorless liquid (sample A) boiling at 48 degrees C was collected. The pressure of the still was then further reduced to 20 mmHg and a final sample (B) of 23 mL of a colorless liquid was collected with a boiling point of 101 degrees C.

Problem 2:

Identify sample B and explain its formation. Sample B was shown to have the composition C9H14O by elemental analysis and mass spectrometry.

Using a graph translating the boiling point under vacuum to boiling point at standard atmospheric pressure, the compound should have a normal bp around 200-210 C. Please identify the compound and explain in as much detail how you came to that conclusion using all three spectras. I know this can be time consuming, but the points given should reflect that.....DETAIL PLEASE!!!

Explanation / Answer

Potassium

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