Oxidation of 9-Fluorenol to 9-Fluornenone

Question 1

What is the advantage of resin-bound chromate?

Answer 1

Simplifies product isolation, controls loss and possible contamination by Cr+6

Question 2

What is the balanced reaction for this procedure?

Answer 2

9-Fluorenol + CrO3 → 9-Fluorenone (use for calculations)

Question 3

What is the balanced redox reaction for this procedure?

Answer 3

3 9-Fluorenol + 6 H+ + 2 CrO3 → 3 9-Fluorenone + 2 Cr+3 + 6 H2O

Question 4

How do you calculate Theoretical Yield for this reaction?

Answer 4

g 9-fluorenol/mm 9-fluorenol * mol ratio(1) * mm 9-fluorenone

Question 5

All Procedure Notes

Answer 5

hot toluene may surge if stirring stops, claisen head on top may help to contain

Withdraw TLC by a pasteur pipet down the condenser, small slug of liquid will stay in the tip, dilute your TLC spl. with CH2Cl2 before spotting.

Spot the TLC plate with a capillary.
Also spot TLC stds.-ketone and alcohol.
Do not cross contaminate std. stock solutions

Question 6

What is the general procedure for this reaction?

Answer 6

Reflux mixture in toluene, (monitor by TLC, color should turn yellow).
Hot amine resin smells bad, use condenser until cooled to ~RT.
Cool, Vacuum filter (small) to separate resin.
Rinse vial, resin with CH2Cl2.
Discard used resin in Chromate waste.
Evaporate toluene/CH2Cl2 in tared beaker.
Weigh product, calc % yield.
Run MP.

Question 7

What will be oxidized?

Answer 7

9-Fluorenol AKA 9-hydroxyfluorene

Question 8

What is the structure of 9-Fluorenol?

Answer 8

A 5 sided carbon ring with two benzene rings attached. An OH attached to the top of the five sided carbon ring.

Question 9

What will be the oxidizing agent?

Answer 9

Amberlyst A-26 resin paired with chromium trioxide

Question 10

What is the structure of Amberlyst A-26 resin paired with chromium trioxide?

Answer 10

Amberlyst A-26= NH4+ OH-

Chromium Trioxide is Chromium with three double bonds to separate oxygens. Write out the two lone pairs on oxygens

Question 11

What is the product of this reaction?

Answer 11

9-fluorenone

Question 12

What is the structure of 9-fluorenone

Answer 12

A five sided carbon with a double bond O on top. Two benzene rings on the side

Question 13

What do we use Acetone for in this experiment?

Answer 13

TLC

Question 14

What is the structure of Acetone?

Answer 14

three carbon long chain with a double bond oxygen on the middle carbon

Question 15

What do we use Toluene for in this experiment?

Answer 15

Solution/supension for the reaction

Question 16

How does the Colorimetric Brethalyzer Test work?

Answer 16

Measure of the color change upon oxidation. Changes from orange to green.

Question 17

What is the structure of Toluene?

Answer 17

Six carbon ring with a ch3 attached

Question 18

Give the structure of dichloromethane, hexane, and methanol

Answer 18

CH2Cl2

C6H14

CH3OH

Question 19

Describe the basic steps to balance a half-cell reaction

Answer 19

write as 2 half cells
balance with coefficients
balance O with H2O
balance H by H+
balance charge with e-
multiply by coefficients
add and cancel

Question 20

Define oxidation and reduction

Answer 20

oxidation= more O, less H, or loss of e-

reduction= less O, more H, or gain of e-