Experiment Summary
Students will work individaully to characterize the reaction behavior of one hydroxyl-containing compound using five different chemical tests.  Each bench in the lab will be stocked with four compounds, one for each student working at the bench.  The compounds at the bench may be a primary alcohol, a secondry alcohol, a tertiary alcohol or a phenol.  There may be one or more of each type of compound at each bench.  Each student will be required to share their results with all students at the bench, and all students are required to report all the results from his or her bench.    Compounds will be labeled with the bench letter and 1, 2, 3, and 4 corresponding to the alcohol.  (eg., alcohols at bench A will be labeled as A-1, A-2, A-3 and A-4.  Please make sure you return your alcohol to the proper bench!).  Each student at the bench will use one of the four alcohols provided and test the alcohol using all five of the following  chemical tests:

• Jones Test
  
• Lucas Test
• Iodoform Test
• KMnO₄ Test
• Br₂/H₂O Test

From the results obtained by each individual student compounds 1, 2, 3 and 4 will be identiified as a primary alcohol, a secondary alcohol, a tertiary alcohol or a phenol.  Based on the results of all the students at the bench, the group will be required to indentify which set of hydroxyl-containing compounds (I-VI, from a provided list given below) corresponds to their bench's set of compounds.  

---

Procedure
Select one of the compounds at the bench and record the bench letter and compound number on the label of the compound selected.  Set up a table in your notebook as indicated below.  Perform each of the chemical tests as described in the individual procedures (click on each link to access the procedure) and fill in the table with your results.  Check the + (plus) column for a positive result or the - (negative) column for a negative result.  Run each test on the known compounds provided at each bench to help determine what a + or - result looks like  for a particular test.  Do not ask lab instructors to interpret the results for you.  Complete the observations column and fill in the column identifying the presence of a specific functional group for tests that give positive results. 

Compound:  __________ (Bench-#)
Test	+	-	Observations	Functional Group Present (for + results)
Jones Test
Lucas Test
Iodoform Test
KMnO4 Test
Bromine/Water Test

Once each student's individual table and results are complete, the results will be shared with other students at the bench to identify specific compounds as a primary, secondary, or tertiary alcohol or a phenol.  Using the group results for all compounds, the group will determine which set of compounds (I-VI), given in the table below corresponds to the bench's set of compounds.  Complete the post lab assignment for the experiment.  

I	II
1-nonanol	3-methyl-2-butanol
fenchyl alcohol	o-cresol
citronellol	3-methyl-3-buten-1ol
p-nitrophenol	tert-pentyl alcohol
III	IV
cyclohexanol	tert-pentyl alcohol
menthol	1-octanol
3-methyl-2-buten-1-ol	2-methylcyclohexanol
cinnamyl alcohol	2-methyl-3-buten-2-ol
V	VI
2-pentanol	1-pentanol
tert-pentyl alcohol	cyclopentanol
3-methyl-1-butanol	o-cresol
1-pentanol	2-methyl-1-butanol