Question

Please help me figure out what A,B, and C are! The bolded is what is provided by the prompt and my notes are the unbolded. IR for Compound B and D shown.

Compound A, C₇H₁₄O₂ did not discharge precipitate in dilute permanganate solution or give a precipitate with 2,4, DNP or with ceric nitrate.

2,4 DNP tests for aldehydes and ketones

Ceric nitrate tests for alcohols

Potassium Permanganate tests for double bonds

So compound A has 1 degree of unsaturation that can't be a double bond. Is it a ring? I don't think there's an epoxide because reacted with acid or base gives a diol.

Compound A was stable to alkali, but heating with dilute acid solution formed compound B, C₆H₁₄O₂, and C (no molecular formula provided).  Compound B gave a positive ceric nitrate test, but no precipitate with 2,4 DNP. IR spectrum below. Compound B when reacted with concentrated with sulfuric acid to give a methyl ketone, C₆H₁₂O, Compound D. When Compound D reacts with iodoform it gives a precipitate and upon reacidification it yields compound E, a carboxylic acid.

COMPOUND 19B 3000 4000 3000 2.300 101 CML MORONS COMPOUND 19D MIGNON COMPOUND 19E 5000 400 MICRONS 3€

Compound B is an alcohol but not an aldehyde or ketone.

There are no degrees of unsaturation

Compound C had significant peaks in the mass spectrum at m/e 28,29, and 30. The last two peaks were the most intense and of nearly equal relative abundance.

I'm stuck. How do you remove only one carbon?

Not sure what is meant by the comment "Book"