(i) Reduction of 4-t-butylcycloheanone

25 mL of methanol
1.5 g of 4-t-
butylcyclohexanone

Add
100 mL conical flask
Boiling chips Add
Heat the solution to boiling
Stir and allow the ice to melt
20 mL of petroleum
spirit
Using the collected aqueous layer
repeat the extraction with fresh
20 mL petroleum spirt
Transfer the petroleum
spirit layer to a small flask
Keep the upper petroleum
spirit layer while running off
the bottom layer into a flask
Heat the mixture for
further 5 minutes after
the addition is complete
30g of crushed ice/5 mL
dilute hydrochloric acid
0.3 g of powdered
sodium borohydride
Add in several small portions
over a period of a few minutes
Combine the two
petroleum spirit layers and
Magnesium sulfate to
remove any water
Add
Evaporate to dryness using
the rotary evaporator
Decant the organic liquid from
the drying agent into a PRE-
WEIGHED round bottom flask
Or
Concentrate the solution in
vacuo using a rotary
evaporator
(ii) Chromatographic separation of the isomers (DO THIS IN PAIRS)


























Compressed air with the needle
valve completely open and it is held
by hand to the top of the column
15% ethyl
acetate/petroleum spirit
Silica is added to a depth of
~15 cm
The compressed air line is
opened slowly and carefully,
flow rate of 20 mL/min
The column is eluted with a
total of 300 mL of 15% ethyl
acetate/petroleum spirit until
the column is packed and all
air bubbles are displaced.
Allow the column to cool
before starting
(iii) Application of the sample



























Dissolve 1.5 g of the product (i)
in a minimum amount of 15%
ethyl acetate/petroleum spirit
Run the column solvent until the
solvent surface is just above the
silica layer.
Release the pressure and close
the bottom tap
Using a pipette, place the isomer
solution onto the head of the column
by dribbling it down the inside surface
of the column
Carefully open the bottom tap (DO
NOT USE THE FLOW CONTROLLER AT
THIS POINT) to allow the solvent level
to drop to the level of the silica layer.
Carefully add a small (~2-3 mL)
volume of eluting solvent with a
pipette and run this volume of solvent
through the column
Repeat TWICE more using portions of
3-5 mL of ethyl acetate in petroleum
spirit.
Add a third portion of solvent
carefully, before carefully topping up
the column with fresh solvent until
theheadspace above the column is
filled with solvent.
Re-attach the flow controller and
elute fractions at a flow rate of 20
mL/min. ALWAYS RELEASE the
PRESSURE carefully when stop
elution.
As solvent emerges at the bottom of
the column, collect it in fractions (20-
25 mL) in test tubes or sample tubes.
During the elution, a band of fine
white crystals may appear on the tip
of the column and should be washed
into the collection vessel using a few
mL of solvent just before each change
of fraction.
Continue collecting 20-25 mL
fractions until accumulation of
crystals on the column tip has almost
ceased
Proceed to TLC analysis using 15%
ethyl acetate in petroleum spirit.
Remember to close the lower
tap while you are adding
fresh solvent so that the
column does not run dry.
If only one product has eluted,
continue eluting using 15% ethyl
acetate/petroleum siprit (about 200
mL) until TLC confirms the second
isomer is eluted. Then change to
100% ethyl acetate to complete
elution of the second isomer.
(iv) TLC Analysis

















Take a pre-cut silica TLC plate
(from prep room)
Draw a faint line in pencil across the
narrow edge of the plate at about 1 cm
height above the base of the plate.
Mark 3 spots evenly across the plate.
Take a TLC spotter (prep room) and dip it
into one of the sample solutions

Carefully and quickly touch the loaded
spotter (to minimize the size) onto the
silica plate

Blow gently on the plate to dry the spot
and repeat the procedure for other
sample fractions.

Calculation of Rf value:

Develop the TLC plate in a lipless beaker fitted with a watch-glass lid:

Line the inside of the container with
filter paper to saturate the atmosphere
with solvent vapour

Place sufficient solvent: 15% ethyl acetate
in petroleum spirit (fumehood) in the
beaker to saturate the filter paper and
leave 0.5 cm solvent in the bottom

Place the TLC plate in the beaker and allow
the solvent to run close to the top of the
plate

Remove the TLC plate with tweezers and
mark the solvent front with a pencil.

Allow it to dry, then visualize the dried
plate immediately by dipping it in
potassium permanganate dip solution.
Record the appearance of the TLC plate.
Record Rf values for each spot.