Post lab for Dehydration of Cyclohexanol

Annie Lu & Minh Nguyen

CHEM 251 - Dr. Joe
1) Complete mechanism for the reaction:

E1 reaction:

SN1 reaction:

2) 5mL cyclohexanol = 4.81g cyclohexanol (Dcyclohexanol = 0.962 g/mL)

% yield =

Actual mass
=
Theoretical yield

1.2216 g
100 =30.97
4.81 g
82.143 g /mol
100.158 g /mol

3) We washed the organic layer with saturated NaHCO3 in order to decrease the solubility of the
organic layer into the aqueous layer, allowing the two layers to separate easily. Then we used
Brine (solution of NaCl with water) to remove the water from the organic phase; and also, we
used Na2SO4 as the drying agent to absorb all the water from the product. Overall, the purpose of
each wash in the work-up is to make the highest purity for the final product.
4) We dont have to worry about the SN1 product because it is the same as starting material.
5) The bromine reagent has a reddish-orange color. When it is dripped slowly into a sample that
contains alkene, the bromine reacts with the alkene to form a nearly colorless dibromide. As the
bromine is consumed, the mixture loses the reddish-orange color. If a sample decolorizes
bromine under these conditions it can be inferred that there is likely an alkene functional group
in the sample.

Colorless

Orange/yellow