Cyclohexene from Cyclohexanol

Organic Chemistry Virtual Lab (Guide)

Summer I 2021

Objectives

To prepare cyclohexene (alkene) by an acid-catalyzed dehydration of cyclohexanol

(alcohol)

Introduction

Review Chapter 19

Here’s a link to a video explaining the mechanisms of acid-catalyzed dehydration. (Only

watch this video if the mechanism provided in the chapter was insufficient for
understanding the reaction).

https://www.youtube.com/watch?v=XzVvqB1tWeM

Experimental Procedure
A student carried out the following experiment in the preparation of cyclohexene by the
acid-catalyzed dehydration of cyclohexanol.

Chemical Reaction:

Introduce 2.0 g of cyclohexanol followed by 0.5 mL of 85% phosphoric acid and a

boiling chip into a 5-mL round-bottomed, long-necked flask. Add a copper sponge to the
neck of the flask and shake to mix the layers. Heat will evolve. Use the arrangement for
fractional distillation. Wrap the fractionating column and distillation head with glass
wool or cotton. Heat the mixture on a sand bath and then distill until the residue in the
flask has a volume of about 0.5 mL. Let the assembly cool slightly before removing the
thermometer. Add 2 mL of toluene into the top of the column using a Pasteur pipette.
Wash the mixture with an equal volume of saturated sodium chloride solution, remove
the aqueous layer, and then add sufficient anhydrous calcium chloride to the organic layer
and let it stand for at least 5 minutes. Using a Pasteur pipette, remove the organic layer
and transfer it to a clean and dry distillation flask, add a boiling chip, and distill the
product. Note cyclohexene boils at 83°C.
Experimental video (recommended): https://www.youtube.com/watch?v=09CDqovJgKA

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Cyclohexene from Cyclohexanol
Organic Chemistry Virtual Lab (Guide)
Summer I 2021

Result
Assume that 1.28g of cyclohexene is produced

Discussion
Using the information above, prepare a complete lab report. This lab report must contain
all sections of the lab report. Include the detailed calculation of % yield. If the % yield
isn’t 100, provide possible explanations based on the experimental video (above) why the
yield is less or more than ideal.

Question

Provide answer to question #2 by drawing the chemical structures of the molecules (not
names).