Please help me to do the table of reagents and products of the experiment: Oxidation of cyclohexanol to cyclohexanone.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question

Please help me to do the table of reagents and products of the experiment: Oxidation of cyclohexanol to cyclohexanone.

42
EXPERIMENT 4: OXIDATION OF CYCLOHEXANOL TO CYCLOHEXANONE
Procedure:
Remember to prepare your notebook before arriving at the lab, including the Table of
Reagents and Expected Products.
1. Set up your apparatus as shown in the figure below, as close to the hood as possible. Gently
slide a Teflon-coated magnetic stir bar into the 3-neck 250-ml RB flask. The thermometer is
held in place by a thermometer adaptor. All ground glass joints should be lightly greased as
usual. The reflux condenser does not need to be connected to tap water.
Reflux Condenser
Separatory Funnel-
3-neck 250-mL RB Flask
Magnetic Stirrer
Thermometer
Thermometer Adaptor
Magnetic Stir Bar
2. Place 0.0700 mol (How many mL would this be?) of cyclohexanol into the RB flask. To it add
6.00 mL of glacial acetic acid.
CAUTION: Handle glacial acetic acid with care! This is pure acetic acid. It is
strongly corrosive and causes serious burns. It is very harmful if swallowed. It is a
lachrymator (a substance that causes your eyes to water). Do not confuse glacial acetic
acid with vinegar, which is only 5% acetic acid.
3. Turn on the stirrer slowly (not the heater!). Make sure the stir bar will not hit the tip of the
thermometer. Add 82 mL of a 8.25 % w/w bleach solution (NaOCI (aq)) into the separatory.
funnel and slowly drip the bleach into the solution at such a rate that the temperature stays
between 40-50 °C. The reaction is exothermic and you do not need to heat this reaction with
the hot plate. However, do not allow the temperature to go below 40°C as the oxidation would
be incomplete.
4. After all of the bleach has been added and the temperature starts to cool, stir for 15 minutes,
then test the solution with starch iodide paper for excess bleach: This is done by first
moistening the starch iodide paper with water, then bringing a drop of the solution (from the
Transcribed Image Text:42 EXPERIMENT 4: OXIDATION OF CYCLOHEXANOL TO CYCLOHEXANONE Procedure: Remember to prepare your notebook before arriving at the lab, including the Table of Reagents and Expected Products. 1. Set up your apparatus as shown in the figure below, as close to the hood as possible. Gently slide a Teflon-coated magnetic stir bar into the 3-neck 250-ml RB flask. The thermometer is held in place by a thermometer adaptor. All ground glass joints should be lightly greased as usual. The reflux condenser does not need to be connected to tap water. Reflux Condenser Separatory Funnel- 3-neck 250-mL RB Flask Magnetic Stirrer Thermometer Thermometer Adaptor Magnetic Stir Bar 2. Place 0.0700 mol (How many mL would this be?) of cyclohexanol into the RB flask. To it add 6.00 mL of glacial acetic acid. CAUTION: Handle glacial acetic acid with care! This is pure acetic acid. It is strongly corrosive and causes serious burns. It is very harmful if swallowed. It is a lachrymator (a substance that causes your eyes to water). Do not confuse glacial acetic acid with vinegar, which is only 5% acetic acid. 3. Turn on the stirrer slowly (not the heater!). Make sure the stir bar will not hit the tip of the thermometer. Add 82 mL of a 8.25 % w/w bleach solution (NaOCI (aq)) into the separatory. funnel and slowly drip the bleach into the solution at such a rate that the temperature stays between 40-50 °C. The reaction is exothermic and you do not need to heat this reaction with the hot plate. However, do not allow the temperature to go below 40°C as the oxidation would be incomplete. 4. After all of the bleach has been added and the temperature starts to cool, stir for 15 minutes, then test the solution with starch iodide paper for excess bleach: This is done by first moistening the starch iodide paper with water, then bringing a drop of the solution (from the
EXPERIMENT 4: OXIDATION OF CYCLOHEXANOL TO CYCLOHEXANONE
black, showing presence of unreacted bleach. Because the exact concentration of hypochlorite
lower layer) with a glass stirring rod and touching it to the test paper. The paper should turn
in the bleach solution depends upon its age, it is necessary to make sure that you have an excess
of hypochlorite to generate the hypochlorous acid, thus ensuring that the cyclohexanol has been
and carry the reaction out 5 minutes longer. Test again with starch iodide paper to check that
fully oxidized. If the test shows that excess bleach is not present you must add 10 mL of bleach
excess bleach is indeed present. If necessary, add more bleach and run the reaction longer.
Repeat this step as necessary until the starch iodide test is positive (test paper turns black).
5. After the reaction is completed, the excess hypochlorous acid must be decomposed with a few
mL of a saturated sodium bisulfite solution. Add enough sodium bisulfite until the starch
iodide test is negative (test paper does not turn black). A few mL may be needed.
6. To neutralize the acetic acid to avoid co-distillation with the cyclohexanone, place a few drops
of thymol blue indicator in the reaction flask and add enough 6 M NaOH solution (about 15-20
mL) until the solution is neutral as indicated by its blue color.
7. Modify your apparatus to do a simple steam distillation by attaching a distillation head,
thermometer adapter, thermometer and West condenser to the center opening of the reaction
flask. Add a couple of boiling chips. Stopper the two side openings with ground glass
stoppers. Replace the magnetic stirrer with a heating mantle connected to a Variac. Attach
rubber hoses to the condenser. (No floods please!) Have your instructor check your setup
before you begin the distillation! Distill over about 50 mL of the solution.
Thermometer Adaptor-
Distillation Head
Side Openings Stoppered
with Glass Stoppers
Heating Mantle
Iron Ring
Blue Clip
H₂O IN
from Tap
H₂0
43
OUT to drain
Heating Mantle plugged into Variac
West Condenser
clamped to
another ring stand
for support
Transcribed Image Text:EXPERIMENT 4: OXIDATION OF CYCLOHEXANOL TO CYCLOHEXANONE black, showing presence of unreacted bleach. Because the exact concentration of hypochlorite lower layer) with a glass stirring rod and touching it to the test paper. The paper should turn in the bleach solution depends upon its age, it is necessary to make sure that you have an excess of hypochlorite to generate the hypochlorous acid, thus ensuring that the cyclohexanol has been and carry the reaction out 5 minutes longer. Test again with starch iodide paper to check that fully oxidized. If the test shows that excess bleach is not present you must add 10 mL of bleach excess bleach is indeed present. If necessary, add more bleach and run the reaction longer. Repeat this step as necessary until the starch iodide test is positive (test paper turns black). 5. After the reaction is completed, the excess hypochlorous acid must be decomposed with a few mL of a saturated sodium bisulfite solution. Add enough sodium bisulfite until the starch iodide test is negative (test paper does not turn black). A few mL may be needed. 6. To neutralize the acetic acid to avoid co-distillation with the cyclohexanone, place a few drops of thymol blue indicator in the reaction flask and add enough 6 M NaOH solution (about 15-20 mL) until the solution is neutral as indicated by its blue color. 7. Modify your apparatus to do a simple steam distillation by attaching a distillation head, thermometer adapter, thermometer and West condenser to the center opening of the reaction flask. Add a couple of boiling chips. Stopper the two side openings with ground glass stoppers. Replace the magnetic stirrer with a heating mantle connected to a Variac. Attach rubber hoses to the condenser. (No floods please!) Have your instructor check your setup before you begin the distillation! Distill over about 50 mL of the solution. Thermometer Adaptor- Distillation Head Side Openings Stoppered with Glass Stoppers Heating Mantle Iron Ring Blue Clip H₂O IN from Tap H₂0 43 OUT to drain Heating Mantle plugged into Variac West Condenser clamped to another ring stand for support
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Organopalladium Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY