Oxidation of 9-Fluorenol to 9-Fluornenone Flashcards Preview

Z - Chem 2229 (Organic Chemistry II Lab) > Oxidation of 9-Fluorenol to 9-Fluornenone > Flashcards

Flashcards in Oxidation of 9-Fluorenol to 9-Fluornenone Deck (20)
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1

What is the advantage of resin-bound chromate?

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

2

What is the balanced reaction for this procedure?

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

3

What is the balanced redox reaction for this procedure?

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

4

How do you calculate Theoretical Yield for this reaction?

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

5

All Procedure Notes

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

6

What is the general procedure for this reaction?

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.

7

What will be oxidized?

9-Fluorenol AKA 9-hydroxyfluorene

8

What is the structure of 9-Fluorenol?

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

9

What will be the oxidizing agent?

Amberlyst A-26 resin paired with chromium trioxide

10

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

Amberlyst A-26= NH4+ OH-

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

11

What is the product of this reaction?

9-fluorenone

12

What is the structure of 9-fluorenone

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

13

What do we use Acetone for in this experiment?

TLC

14

What is the structure of Acetone?

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

15

What do we use Toluene for in this experiment?

Solution/supension for the reaction

16

How does the Colorimetric Brethalyzer Test work?

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

17

What is the structure of Toluene?

Six carbon ring with a ch3 attached

18

Give the structure of dichloromethane, hexane, and methanol

CH2Cl2

C6H14

CH3OH

19

Describe the basic steps to balance a half-cell reaction

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

20

Define oxidation and reduction

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

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