1. Write the overall equation for this reaction using complete structural formulas for the cyclohexanol and cyclohexanone.

(you don't need to balance the equation or show the mechanism).

2. Under the cyclohexanol and cyclohexanone structures write their refractive index at 20 degrees C (sodium D line)

cyclohexanol= 1.4641 and cyclohexanone= 1.4507

3. Assuming only cyclohexanol and cyclohexanone are in the experimental product mixture, place the letter of the choice

that most likely explains the corrected experimental refractive index (RI) given in questions 3.1, 3.2 and 3.3.

Explanations: A) the mixture has mostly cyclohexanol in it and little target product was made.

B) the mixture has mostly cyclohexanone in it and is relatively pure.

C) the mixture has a lot of both cyclohexanol as well as cyclohexanone in it and the reaction was relatively incomplete.

3.1 Product mixture's RI = 1.4577, explanation_________

3.2 Product mixture's RI = 1.4625, explanation__________

3.3 Product mixture's RI = 1.4527, explanation__________

4. Using the Infrared (IR) Correlation table in your Organic Chem II Lab Manual, CRC or other reputable source, make structural unit assignments for each of these typical IR absorptions in questions 4.1, 4.2, 4.3 and 4.4 that would appear in the spectrum of cyclohexanol and/or cyclohexanone. Possible structural units are sp3 C/O bond of an alcohol, sp3 C/H bond, O/H bond of an alcohol and a C/O double bond unit of a ketone.

4.1 Strong peak at about 1715 1/cm ______________________________

4.2 Strong peak at about 2950 1/cm____________________________

4.3 Sharp peak at about 1070 1/cm_______________________________

4.4 Broad peak at about 3350 1/cm_____________________________

4.5 Clearly circle the structural units on the structural formulas of cyclohexanol and cyclohexanone that were responsible for the IR absorptions in questions 4.1, 4.2, 4.3, 4.4 and label them.

4.6 If the experimental product mixture produced in the reaction of question #1 gave an IR spectrum with a strong absorption at about 1715 1/cm and little absorption at about 3350 1/cm would this evidence be consistent with the production of relatively pure cyclohexanone ?

Explain why or why not in complete logical sentences.