Question

unknown solid organic chemistry 2 experiment, please help in determining my solid

Here's my data so far, I'll be continuing next week:

-Melting point of the unknown is 209-215 degrees C

-Solid unknown itself is a white crushed powder with a strong smell

-Insoluble in 5% NaOH, Water, 5% HCl but soluble in H2SO4 and 95% ethanol

-Negative DNPH test with no precipitate

-Positive chromic acid test with a green precipitate

So i'm thinking i received a borneol compound. How should i proceed? or am i right or wrong?

Answer 1

Since this insoluble in water,5% NaOH and 5% HCl, this will have functional group of Alkene,Aldehyde,Ketone or Alcohol.

This is showing negative DNPH test, that means this can't be any kind of aldehyde or ketone.

Again this is giving positive chromic aid test,it indicates the presence of aldehyde or alcohol goup.From these two tests, we can conclude that this compund is having alcohol goup. This compond an't be phenolic types,since it is insouble in 5% NaOH.

Again the m.p. is in the range of 209-215 ⁰C, this compund will be borneol type of compound,since it is white in colour and having a strong odor like camphor.