EXPT. 4: practical exam (Orgo Chem Lab II)

Help me study for my Chemistry class. I’m stuck and don’t understand.

The assignment

You will be assigned three unknown organic compounds that will belong to one of the following functional group categories:


alcohol (primary, secondary or tertiary)

2o 2-alkanol

amine (primary, secondary or tertiary)

carboxylic acid





Each unknown will possess only ONE of the functional groups listed above, in addition to the possible presence of other substituents/functionality (halogens, ethers, nitro groups, cyano groups, alkene, alkyne, aromatic rings).

Each set of 3 unknowns is assigned RANDOMLY

Each unknown is numbered, & assignments are made using software that generates one set of 3 unique random unknown numbers for each student in the class, so it is possible that more than one of your assigned unknowns could fall into the same functional group category.

The following information will be provided for each unknown:

  1. Molecular weight
  2. Elemental analysis data (i.e., %C, %H, etc.)
  3. Solubility test results (following the solubility scheme provided in the lab lecture notes)
  4. Classification test results (only those listed below – classification test results are provided based on solubility test results, and only those results are provided that give you useful information)
  • Jones oxidation (chromic acid test)
  • 2,4-dinitrophenyl hydrazine (2,4-DNP) test
  • Iodoform test
  • Litmus test
  • Iron (III) chloride test

e. 1H NMR data – with peak integration & multiplicities (or spectral expansions)

f. 13C NMR data – with the number of peaks indicated

On each assignment sheet, in the spaces provided, you must provide the following information about each unknown:

  1. Molecular formula
  2. Preliminary conclusion regarding functional groups that might be present in the unknown based ONLY on the solubility/reactivity results
  3. Preliminary conclusion regarding the functional group that might be present in the unknown based on BOTH the solubility/reactivity results ANDthe classification test results
  4. A neatly & clearly drawn chemical structure of the unknown based on the given spectral data and your conclusions from solubility and classification tests