Experiment #1
docx
keyboard_arrow_up
School
Collin County Community College District *
*We aren’t endorsed by this school
Course
MISC
Subject
Chemistry
Date
Feb 20, 2024
Type
docx
Pages
6
Uploaded by MagistrateAlbatrossMaster436
3210.
Experiment #1: Oxidation of Cyclohexanol to Cyclohexanone
Objective:
The objective of this experiment is to synthesize cyclohexanone and confirm the product by functional group analysis.
Reaction equation:
Materials:
Instruments and glassware for distillation set up, thermometer, spatula, pH paper, starch iodide paper, boiling chips, glass stir rod, cyclohexanol, acetic acid, sodium hypochlorite, thymol blue, saturated sodium bisulfite solution, 6M NaOH solution, Ether, and NaCl.
Reference table:
Reagent
MM
MP
Safety Hazard
Structure
Cyclohexanol
100.16 g/mol
25.93 C
Irritant
Acetic acid
60.05 g/mol
16.6 C
Flammable, Corrosive
Sodium hypochlorite
74.44 g/mol
18 C
Corrosive, Environmental hazard
Thymol blue
466.6 g/mol
283-285 C
Irritant
Saturated bisulfite solution
104.6 g/mol
150 C
Irritant
NaOH solution
39.997 g/mol
318 C
Corrosive
NaCl
58.44 g/mol
801 C
Irritant
Ether
74.12 g/mol
-116.3 C
Flammable, Irritant
Procedure:
1.
Fill beaker half full of water and place on a hot plate. Check temperature for 45 C.
2.
Measure 150mg of Cyclohexanol. Record the amount.
3.
Measure 70-100mg of acetic acid into a 5mL long-necked round-bottom flask.
4.
Measure 2mL of 6% sodium hypochlorite solution then add the total volume to the 5mL long-necked round-bottom flask. Gently swirl contents of the flask for three minutes. Note any observations with temperature.
5.
Check the pH of the mixture using the iodide paper. Test for presence of hypochlorite using the starch iodide paper. If the iodide paper gives a negative test, add two drops of sodium bisulfite to the reaction. Test again. Add more sodium bisulfite if needed.
6.
If first result was negative, add more hypochlorite solution. Place on hotplate and test again. Redo starch iodide test for a negative result.
7.
Add a few drops of thymol blue, then add 6M of NaOH to the long-necked round-bottom flask. Record observations.
8.
Set up distillation apparatus. Cool the solution to rt after.
9.
Add 2 drops of solution into 2,4-DNP. Record Observations.
10. Salt out by adding NaCl to reaction mixture.
11. Extract using 2-3mL of ether. Perform at least 2 times.
12. Evaporate organic layer by heating. Use wooden sticks to prevent bumping.
Data/Observations: Measurement
Starting amount of cyclohexanol
.15g
Starting mount of azelaic acid
.68g
Amount of sodium chloride added to cyclohexanone and water distillate
.102g
Mask of pre-weighed flask
16.9g
Mask of flask with organic layer
17.45g
Acidic solution felt warm/hot after sodium hypochlorite was added.
After solution was heated, it tested negative for hypochlorite.
Tested positive for hypochlorite when flask was cooled.
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
- Access to all documents
- Unlimited textbook solutions
- 24/7 expert homework help
Inorganic layer was cloudy/ blurry, organic layer appeared clear.
Percent yield: (17.45-16.9)/ .15= 3.66 3.66x100= 366%
**percent yield indicates an error must have taken place during the experiment.
Conclusion:
In this experiment, cyclohexanone was synthesized from cyclohexanol. Cyclohexanol was oxidized with hypochlorite as the oxidizing agent. However, the experiment was not completely successful. A percent yield of 366% indicates some sort of error has occurred during the experiment. The starting amount of cyclohexanol was .15 grams, so it is impossible to have more
than what was started with. It is possible that there may have been some brine solution in the flask when the final mask was calculated. Also, there were also some issues with the distillation setup. Too many boiling chips were added which causes the solution to boil rapidly, the cyclohexanone solution could have evaporated
too quickly. Future suggestions include carefully extracting the brine solution and not using too many boiling chips.
Prelab questions:
1.
Is there any significance for making cyclohexanone in the industry?
Cyclohexanone is a good solvent for organic phosphorous pesticides.
2.
Explain the reasons for the selection of NaOCl for the oxidation reactions vs chromium based oxidizing reagent in the labs?
What is the role of acetic acid in this lab? Chromium reagents are hazardous and difficult to use in labs and dispose, however the salt that forms during the hypochlorite reaction makes disposing easier. The role of acetic acid is to react with NaOCl to form HOCl which oxidizes OH to a ketone.
Post-lab questions:
1.
What are the techniques that you learned in 3210 labs are applied here in this experiment? Explain your rationale for the selection. Techniques learned in 3210 labs that were applied in this experiment include distillation. Distillation works by evaporating
a solution once its boiling point is reached. Extraction was also performed in 3210 labs and in this experiment. Performing extraction allows us to separate the organic layer from
the inorganic layer.
2.
What is the significance of pH adjustment in this experiment? pH adjustment is important because an acidic solution is required. The acid acts as a catalyst in the reaction
turning NaOCl into HOCl.
References:
National Center for Biotechnology Information. "PubChem Compound Summary for CID 3283, Ether"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Ether
. Accessed 31 January, 2022.
National Center for Biotechnology Information. "PubChem Compound Summary for CID 7966, Cyclohexanol"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Cyclohexanol
. Accessed
31 January, 2022.
National Center for Biotechnology Information. "PubChem Compound Summary for CID 176, Acetic acid"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Acetic-acid
. Accessed 31 January, 2022.
National Center for Biotechnology Information. "PubChem Compound Summary for CID 23665760, Sodium hypochlorite"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-hypochlorite
. Accessed 31 January, 2022.
National Center for Biotechnology Information. "PubChem Compound Summary for CID 65565, Thymol blue"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Thymol-blue
. Accessed 31 January, 2022.
National Center for Biotechnology Information. "PubChem Compound Summary for CID 23665763, Sodium bisulfite"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-
bisulfite
. Accessed 1 February, 2022. National Center for Biotechnology Information. "PubChem Compound Summary for CID 14798, Sodium hydroxide"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-
hydroxide
. Accessed 1 February, 2022.
National Center for Biotechnology Information. "PubChem Compound Summary for CID 5234, Sodium chloride"
PubChem
,
https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-chloride
. Accessed 1 February, 2022.
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
- Access to all documents
- Unlimited textbook solutions
- 24/7 expert homework help
Related Documents
Related Questions
Answer the following questions following a Solubility and recrystalization lab for organic chemisty.
1. In a solubility and recrystallization lab you are working with the following chemicals : solids (benzoic acid, acetanilide,naphthalene, and resorcinol) and three solvents (water, ethanol and petroleumether) discuss and rank the polarity of the solvents and the polarity of the compounds being investigated.
2. Briefly describe how a mixture of sand and benzoic acid (soluble in hotwater) could be separated to produce pure benzoic acid.
arrow_forward
Data:
Density of p-phenetidine is 1.065g/mol
Williamson Ether Synthesis:
Mass of filter paper: 0.680 g
Mass of filter paper and product: 1.482 g
Melting Point: 134-136oC
Amide Synthesis:
Mass of filter paper: 0.686 g
Mass of filter paper and product: 1.589 g
Melting Point: 135-137oC
Mixed Melting Point (product of amide synthesis mixed with Williamson Ether synthesis product): 134-136oC
(a)Calculate theoretical yield of both williamson ether synthesis of phenacetine and amide synthesis of phenacetin.
(b) calculate the percent yield of phenacetin obtained via williamson ether synthesis.
(c) Calculate the percent yeild of phenacetin obtained via the amide synthesis.
arrow_forward
Please answer the question at the bottom, Thanks.
LAB NOTES FOR PREPARATION OF BUTYL MAGNESIUM BROMIDEAND ITS SUBSEQUENT CONVERSION TO AN ALCOHOL
To the reaction flask were added 2.5967 gram of magnesium turnings, about 20 mlof diglyme, and a solution of 13.5942 gram of butyl bromide in about 25 mldiglyme.The procedure as per the lab manual was initiated. After the required heating timewas completed the reaction mixture was allowed to cool to room temperature.Then a solution of 6.1123 gram of acetone in about 15 ml of diglyme was addeddropwise as per the lab manual.The rest of the lab manual procedure was completed, ultimately affording 2.5532gram of an oily, clear and slightly yellow liquid, presumed to be 2-methyl-2-hexanol. Boiling point as measured by distillation was 138 – 141 deg C.About 0.8 ml of the presumed 2-methyl-2-hexanol was placed in an NMR tube towhich was added 2 drops of TMS. The tube was capped, then inverted and righted20 times to thoroughly mix the product and…
arrow_forward
Please answer the question at the bottom, Thanks.
LAB NOTES FOR PREPARATION OF BUTYL MAGNESIUM BROMIDEAND ITS SUBSEQUENT CONVERSION TO AN ALCOHOL
To the reaction flask were added 2.5967 gram of magnesium turnings, about 20 mlof diglyme, and a solution of 13.5942 gram of butyl bromide in about 25 mldiglyme.The procedure as per the lab manual was initiated. After the required heating timewas completed the reaction mixture was allowed to cool to room temperature.Then a solution of 6.1123 gram of acetone in about 15 ml of diglyme was addeddropwise as per the lab manual.The rest of the lab manual procedure was completed, ultimately affording 2.5532gram of an oily, clear and slightly yellow liquid, presumed to be 2-methyl-2-hexanol. Boiling point as measured by distillation was 138 – 141 deg C.About 0.8 ml of the presumed 2-methyl-2-hexanol was placed in an NMR tube towhich was added 2 drops of TMS. The tube was capped, then inverted and righted20 times to thoroughly mix the product and…
arrow_forward
Starting Materials
CH3B
CH3CH2BR
CH3CH2CH,Br
C6H5Br
Reagents
Mg, ether
1.
a.
2.
13CH2-13C-OH
b.
13CO2 then H3O*
3.
LIAIH4 then H3o*
PBr3
CO2 then H30*
C.
4.
d.
5.
C6HsCH2Br
е.
Select a starting material and a series of reagents necessary to synthesize this compound in as few steps as possible.
Enter your selection as a number for the starting material, followed by the letters of the reagents, in the order that you wish to use them, i.e. 3abcf.
arrow_forward
You are employed as a coop student at the Drug and Alcohol Testing Association of Canada (DATAC) developing analytical tests for sports doping agents. You are asked to prepare a procedure for the extraction of methylphenidate, the active compound in Ritalin, from urine samples (consider them as simple aqueous layers, you do not need to consider other components!). The goal of the procedure is to extract the methylphenidate into an organic layer which will then be evaporated, and the residue will be tested for the drug.Your colleague is helping you develop the urine test. They suggest that the urine should be adjusted to a pH above 7 before extracting with the organic solvent. Why is this necessary? Support your explanation with a full arrow-pushing mechanism for the reaction that would occur if the pH was below 7. Include all formal charges, intermediates (if applicable) and products.
arrow_forward
You are employed as a coop student at the Drug and Alcohol Testing Association of Canada (DATAC) developing analytical tests for sports doping agents. You are asked to prepare a procedure for the extraction of methylphenidate, the active compound in Ritalin, from urine samples (consider them as simple aqueous layers, you do not need to consider other components!). The goal of the procedure is to extract the methylphenidate into an organic layer which will then be evaporated, and the residue will be tested for the drug.You find that methylphenidate is highly soluble in 2-methyltetrahydrofuran, a bio-renewable solvent. Draw the structure of 2-methyltetrahydrofuran and give two reasons why it is a good solvent choice for liquid-liquid extraction.
arrow_forward
What is the theoretical yield and limiting reagent for the reaction of benzophenone with sodium borohydride to form diphenyl methanol as described in the experiment provided if you begin with 1.75g of benzophenone in 25 mL of 95% ethanol and add 0.75 g of sodium borohydride portion wise over 45 minutes?
arrow_forward
using 0.0015 moles benzaldehyde and 0.0015 moles (carbethoxymethylene) triphenylphosphine
Use 0.15 grams as experimental yield and calculate theoretical and percent yield show all steps
arrow_forward
please solve question 1 and 2, thanks alot sir for ur help, note that this is not a graded question, its a past paper
arrow_forward
Draw the structure of the major organic product you would expect from the reaction of 1-bromopropane with Nal.
You do not have to explicitly draw H atoms.
• Draw only the product derived from 1-bromopropane. Do not draw other organic by-products.
arrow_forward
I need help with understanding these questions. These questions are not writing/researching responses.
arrow_forward
What factors during the experiment caused the percent yield to be different than 100%? What impurities may be present in the final product (look at the spectroscopic data for evidence of this), and how does that effect the percent yield calculation?
I got 64% for the percent yield.
arrow_forward
The theoretical yield of 1-methylcyclohexene in moles(from 2-methylcyclohexanol amount of 2.239 gram). The theoretical yield of 1-methylcyclohexene in moles is 0.01961.
1. What is the corrected actual yield(% Relative Area for 1-methylcyclohexene is 82.81%)? The theoretical yield of 1-methylcyclohexene in moles is 0.01961.
2. . What is the calculation of the %yield of 1-methylcyclohexene?
arrow_forward
Checking my answer, there was difference with solution.
(organic chemistry smith 5th ed 2.47P (d))
Solution said 'the acid base reaction between pentyne and ammonia is product way because pka of pentyne is 25, ammonia is 38 so pentyne will be deprotanted by ammonia.'
but I think (and as written in the book) NH4+ is stronger acid than pentyne and acid-base reaction works when reactant is stronger acid than product conjugate acid. It isn't match that pentyne makes NH4+.
who is incorrect?
arrow_forward
An organic chemistry laboratory Extraction; the extraction of crude naphtalene- benzoic acid mixture. Naphthalene is a suspect carcinogen and is toxic to aquatic life. Find an alternative pair of molecules that adhere better to the principles of green chemistry and can be separated by extraction using green' solvents. (kindly answer fully)
arrow_forward
help please answer in text form with proper workings and explanation for each and every part and steps with concept and introduction no AI no copy paste remember answer must be in proper format with all working
arrow_forward
Suppose you took your two compounds, dissolved them in tertbutyl methyl ether and then added them to a separatory funnel. Now suppose you add in aqueous sodium bicarbonate and vigorusly shake the contents of the separatory funnel.
ethanol will be dissolved in tert butyl methyl ether ether and valeric acid will be dissolved in the aqueous sodium bicarbonate layer.
Draw the EXACT chemical structure that will exist in each of the layers after shaking with sodium bicarbonate. (Is it neutral or charged?)
arrow_forward
Ee.83.
arrow_forward
..) Fill in the blanks with the NAME and
STRUCTURE of the ORGANIC REACTANT or the NAME and STRUCTURE
of the MAJOR ORGANIC PRODUCT in the following reactions:
Fused KOH, 200°C
A. 2,2-dichloroheptane
-x ?
(name, str)
Hydroboration
В.
?
--< Hexanal CH3CH2CH2CH2CH2CHO
(name, str)
C. ?
(name, str)
--Оз, НгО--
--X Butanoic acid CH3CH2CH2COOH
NANH2, 150°C
D.
1,2-dichlorobutane
-X ?(name, str)
arrow_forward
Calculate theoretical yield of the Grignard reaction synthesis of triphenylmethanol from bromobenzene. Amounts of products used are listed in the image.
arrow_forward
SEE MORE QUESTIONS
Recommended textbooks for you

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Related Questions
- Answer the following questions following a Solubility and recrystalization lab for organic chemisty. 1. In a solubility and recrystallization lab you are working with the following chemicals : solids (benzoic acid, acetanilide,naphthalene, and resorcinol) and three solvents (water, ethanol and petroleumether) discuss and rank the polarity of the solvents and the polarity of the compounds being investigated. 2. Briefly describe how a mixture of sand and benzoic acid (soluble in hotwater) could be separated to produce pure benzoic acid.arrow_forwardData: Density of p-phenetidine is 1.065g/mol Williamson Ether Synthesis: Mass of filter paper: 0.680 g Mass of filter paper and product: 1.482 g Melting Point: 134-136oC Amide Synthesis: Mass of filter paper: 0.686 g Mass of filter paper and product: 1.589 g Melting Point: 135-137oC Mixed Melting Point (product of amide synthesis mixed with Williamson Ether synthesis product): 134-136oC (a)Calculate theoretical yield of both williamson ether synthesis of phenacetine and amide synthesis of phenacetin. (b) calculate the percent yield of phenacetin obtained via williamson ether synthesis. (c) Calculate the percent yeild of phenacetin obtained via the amide synthesis.arrow_forwardPlease answer the question at the bottom, Thanks. LAB NOTES FOR PREPARATION OF BUTYL MAGNESIUM BROMIDEAND ITS SUBSEQUENT CONVERSION TO AN ALCOHOL To the reaction flask were added 2.5967 gram of magnesium turnings, about 20 mlof diglyme, and a solution of 13.5942 gram of butyl bromide in about 25 mldiglyme.The procedure as per the lab manual was initiated. After the required heating timewas completed the reaction mixture was allowed to cool to room temperature.Then a solution of 6.1123 gram of acetone in about 15 ml of diglyme was addeddropwise as per the lab manual.The rest of the lab manual procedure was completed, ultimately affording 2.5532gram of an oily, clear and slightly yellow liquid, presumed to be 2-methyl-2-hexanol. Boiling point as measured by distillation was 138 – 141 deg C.About 0.8 ml of the presumed 2-methyl-2-hexanol was placed in an NMR tube towhich was added 2 drops of TMS. The tube was capped, then inverted and righted20 times to thoroughly mix the product and…arrow_forward
- Please answer the question at the bottom, Thanks. LAB NOTES FOR PREPARATION OF BUTYL MAGNESIUM BROMIDEAND ITS SUBSEQUENT CONVERSION TO AN ALCOHOL To the reaction flask were added 2.5967 gram of magnesium turnings, about 20 mlof diglyme, and a solution of 13.5942 gram of butyl bromide in about 25 mldiglyme.The procedure as per the lab manual was initiated. After the required heating timewas completed the reaction mixture was allowed to cool to room temperature.Then a solution of 6.1123 gram of acetone in about 15 ml of diglyme was addeddropwise as per the lab manual.The rest of the lab manual procedure was completed, ultimately affording 2.5532gram of an oily, clear and slightly yellow liquid, presumed to be 2-methyl-2-hexanol. Boiling point as measured by distillation was 138 – 141 deg C.About 0.8 ml of the presumed 2-methyl-2-hexanol was placed in an NMR tube towhich was added 2 drops of TMS. The tube was capped, then inverted and righted20 times to thoroughly mix the product and…arrow_forwardStarting Materials CH3B CH3CH2BR CH3CH2CH,Br C6H5Br Reagents Mg, ether 1. a. 2. 13CH2-13C-OH b. 13CO2 then H3O* 3. LIAIH4 then H3o* PBr3 CO2 then H30* C. 4. d. 5. C6HsCH2Br е. Select a starting material and a series of reagents necessary to synthesize this compound in as few steps as possible. Enter your selection as a number for the starting material, followed by the letters of the reagents, in the order that you wish to use them, i.e. 3abcf.arrow_forwardYou are employed as a coop student at the Drug and Alcohol Testing Association of Canada (DATAC) developing analytical tests for sports doping agents. You are asked to prepare a procedure for the extraction of methylphenidate, the active compound in Ritalin, from urine samples (consider them as simple aqueous layers, you do not need to consider other components!). The goal of the procedure is to extract the methylphenidate into an organic layer which will then be evaporated, and the residue will be tested for the drug.Your colleague is helping you develop the urine test. They suggest that the urine should be adjusted to a pH above 7 before extracting with the organic solvent. Why is this necessary? Support your explanation with a full arrow-pushing mechanism for the reaction that would occur if the pH was below 7. Include all formal charges, intermediates (if applicable) and products.arrow_forward
- You are employed as a coop student at the Drug and Alcohol Testing Association of Canada (DATAC) developing analytical tests for sports doping agents. You are asked to prepare a procedure for the extraction of methylphenidate, the active compound in Ritalin, from urine samples (consider them as simple aqueous layers, you do not need to consider other components!). The goal of the procedure is to extract the methylphenidate into an organic layer which will then be evaporated, and the residue will be tested for the drug.You find that methylphenidate is highly soluble in 2-methyltetrahydrofuran, a bio-renewable solvent. Draw the structure of 2-methyltetrahydrofuran and give two reasons why it is a good solvent choice for liquid-liquid extraction.arrow_forwardWhat is the theoretical yield and limiting reagent for the reaction of benzophenone with sodium borohydride to form diphenyl methanol as described in the experiment provided if you begin with 1.75g of benzophenone in 25 mL of 95% ethanol and add 0.75 g of sodium borohydride portion wise over 45 minutes?arrow_forwardusing 0.0015 moles benzaldehyde and 0.0015 moles (carbethoxymethylene) triphenylphosphine Use 0.15 grams as experimental yield and calculate theoretical and percent yield show all stepsarrow_forward
- please solve question 1 and 2, thanks alot sir for ur help, note that this is not a graded question, its a past paperarrow_forwardDraw the structure of the major organic product you would expect from the reaction of 1-bromopropane with Nal. You do not have to explicitly draw H atoms. • Draw only the product derived from 1-bromopropane. Do not draw other organic by-products.arrow_forwardI need help with understanding these questions. These questions are not writing/researching responses.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning