Name: _______________________ Score: _______/57 Percentage: _______%

ACTIVITY NO. 2
ELIMINATION REACTION: PREPARATION OF CYCLOHEXENE from CYCLOHEXANOL

I. Give the over-all reaction: (Label all structural formula) (2pts)

II. Give the complete mechanism of the reaction: (4pts)

III. Complete the following table. (10pts)

MW b.p. Density Vol. Used Weight Used No. of Moles
(g/mol) (˚C) (g/mL) (mL) (g) Used (2pts)

Cyclohexanol

Cyclohexene NA NA NA

IV. Enumerate the hazards of the following: (2pts each)

A. Phosphoric acid:

_____________________________________________________________________________
B. Cyclohexanol:

______________________________________________________________________
C. Cyclohexene:

______________________________________________________________________

V. Yield Data:

Weight of covered reagent bottle: (1pt)___56.20 g______________________

Weight of reagent bottle + product: (1pt) _68.22 g_____________________

Actual Yield: (1pt) _________________________________________________

1
 Theoretical Yield: (3pts) ____________________________________________
Based on the no. of moles of the limiting reagent and the balanced over-all reaction,
calculate the theoretical yield. (show calculation below)

% Yield (2pts): _____________________________________________________

VI. Observed properties of the product: (from the video)
Physical state, color: (2 pts) ___________________________________________

Boiling point (lit. value): (1pt) __________________________________________

VII. Qualitative Tests: (4pts)

Test Br2 in CH2Cl2Result +/- Baeyer’s Test Result +/-
Compound
cyclohexanol No decolorization No decolorization
cyclohexene decolorization decolorization

VII. Questions:

1) In the purification of the product, the cyclohexanol is expected to combine with the aqueous
layer. Explain why. (2pts)

_______________________________________________________________________

2) The procedure states that you should leave about 8 mL of residue when distilling the
crude cyclohexene. What are the reasons for this (what is in the residue)? (2pts)

_______________________________________________________________________

_______________________________________________________________________

3) List one technique used in this experiment to maximize the yield of cyclohexene and
minimize the yield of by-products. (2pts)

_______________________________________________________________________

_______________________________________________________________________

4) Write equations that show the dehydration of 3-pentanol. Two possible products can form,
show both and indicate which one is the major product. (4pts)

_______________________________________________________________________

_______________________________________________________________________

2
5. a) What alcohol would be the most logical choice as the starting material for the
preparation of 1-methylcyclohexene? (1pts) _______________________________

b) Write the over-all equation for this reaction. (2pts)

____________________________________________________________________

6. Referring to the qualitative test, write the equation for the following reactions:

a) cyclohexene + Br2 (2pts)

____________________________________________________________________

b) cyclohexene + KMnO4 (2pts)

____________________________________________________________________

7. Give the Schematic Diagram of the entire flow of the synthesis up to the purification
of the product. You can use separate sheet. (5pts)