[jhazel]

Using the follow tests I have been able to narrow down my unknown as a ketone, but based on these derivatives does anyone have an idea about what ketone it could possible be? The IR indicated a very basic ketone.

Sample Name:
Unknown # 6 (Liquid)

Boiling Point:
160 C

PH:
Neutral

Solubility Test:
H2O:      NO
5% HCl:      NO
5% NaOH:   NO
H2SO¬4:      YES
Highly reactive with H2SO4, producing a lot of heat and polymerizing into a maple colored syrup. 

Ignition Test:
No ignition, flame, or smoke when put to match-flame.

C-5: Bilstein’s Test
Control (chlorobenzene)- Large flame with dark, black smoke
Unknown- Flame with no visible smoke
Result: NEGATIVE

C-2: Alkaline Hydrolysis Test
Control (butyl acetate)- Dark blue ring formed on filter paper
Unknown- Light blue ring formed on filter paper
Result: NEGATIVE

C-9: Chromic Acid Test
Controls (1-butanol, butanal)- Green/blue suspension forms within test tube
Unknown- No immediate suspension formation. No delayed suspension formation.
Result: NEGATIVE

C-11: 2,4-Dinitrophenylhydrazine Test
Controls (cyclohexanone, benzaldehyde)- Bright orange crystal formation
Unknown- Bright orange crystal formation.
Result: POSITIVE

Derivatives:

D-3: 2,4-Dinitrophenylhydrazones
Melting Point: 135C, 138C
Observations: Orange, crystalline

D-4: Semicarbazones
Melting Point: 168C, 165C
Observations: White, crystalline

D-5: Oximes
Melting Point: N/A
Observations: Would not crystallize. Turned milk colored but could not be collected by vacuum filtration

[408]

Normally one has a table for comparison, ex for the melting point of DNPH and semicarbazide derivatives...

Without this you are overcomplicating the problem

[jhazel]

Yeah, we were supposed to just rely on internet resources for the tables. But the possibilities seemed immense.

I just ran the IR in a database and came out with

3-methylcyclohexanone

which matches our melting points quite well for the derivatives(although they were done a bit spottily, so they are not the most accurate). The IR is a perfect match though