231L Ketone Reduction
docx
keyboard_arrow_up
School
Iowa State University *
*We aren’t endorsed by this school
Course
MISC
Subject
Chemistry
Date
Feb 20, 2024
Type
docx
Pages
7
Uploaded by CorporalSheepMaster1026
NEW TEMPLATE: 231L Sodium Borohydride Reduction
Pre-lab Questions
Procedure and Safety
1.
(10 pts) Write a VERY brief bullet point list summary of the procedure.
Synthesize (TCL)
Separate and purify (DCM)
Characterize, (mass, melting point, FTIR)
2.
(18 pts, 3 pts ea) Fill in the following table with amounts to use to make 10 mL of each of the TLC
developing solvents you will test.
% Ethyl Acetate/% Hexanes
Volume Ethyl Acetate (mL)
Volume Hexanes (mL)
30/70
3
7
50/50
5
5
70/30
7
3
3.
(84 pts) This question reviews drawing bond-line structures. In addition, you will identify the purpose for each chemical in the synthesis that you will perform for this experiment. Reading through the procedure carefully will help you identify the chemical purpose. In addition, you will add safety information for each chemical rather than writing the usual safety summary.
Compound
Structure (5 pts ea)
Purpose (3 pts ea)
Hazards (4 pts ea)
methanol
Solvent
Do not drink. Do not use near flames
ethyl acetate
synthesis
Flammable, irritant
hexanes
synthesis
Flammable, enviro damaging, health hazard, skin irritant
sodium borohydride
synthesis
Flammable, methylene chloride
product
toxic
9-fluorenone
synthesis
irritant
9-fluorenol
synthesis
corrosive
hydrochloric acid
synthesis
irritant
Mechanism
4.
The first step in the reduction of an aldehyde or ketone using sodium borohydride is a nucleophilic attack. This is shown below for the reduction of acetone. Sodium borohydride can be considered to by a source of hydride ions as shown.
a.
(4 pts) What is the nucleophile in this step?
H
b.
(4 pts) Why is the carbonyl carbon attacked by a nucleophile?
More electronegative
5.
(20 pts) Draw the first step for the reaction you will do for this experiment: Reduction of 9-
fluorenone using sodium borohydride.
6.
(25 pts) The second step for the sodium borohydride reduction of an aldehyde or ketone is a proton transfer step. This is shown below for the reduction of acetone.
Draw the proton transfer step for the reduction of 9-fluorenone using sodium borohdride.
Amounts to Use 7.
(10 pts) Fill in the following table with amounts to use and theoretical yield for this experiment. Show work for credit.
Starting Material
Reagent
9-fluorenone
Sodium borohydride
Moles
1.4 mmol
0.7 mmol
MW
180.20 g/mol
37.83 g/mol
Amount
?
?
Data and Observations
1.
(15 pts) Insert a photo of your three TLC plates used for testing developing solvents with provided
solutions of 9-fluorenone and 9-fluorenol. The solvent front should be marked, and circles drawn around any spots visualized using UV light. Plates should be clearly labeled with developing solvent used and what was spotted. Photo should include a ruler for calculating R
f
values.
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
2.
(5 pts) Mass of 50 mL Erlenmeyer flask________
3.
(5 pts) Mass of 50 mL Erlenmeyer flask and 9-fluorenone__________
4.
(5 pts) Mass of 9-fluorenone______0.210______
5.
(15 pts) Insert photo of TLC plate showing reaction progress. The solvent front should be marked,
and circles drawn around any spots visualized using UV light. Plates should be clearly labeled with developing solvent used and what was spotted. Photo should include a ruler for calculating R
f
values.
6.
(5 pts) Mass of rotovap flask___88.814_______
7.
(5 pts) Mass of rotovap flask and product_____89.012_______
8.
(5 pts) Melting point of product____148-150C_________
9.
(20 pts) Insert a photo of your FTIR spectrum for your product. Draw the structure of 9-fluorenol on or near the spectrum. Label the peaks in the spectrum which correspond to functional groups in your product.
Analysis and Application Questions Analysis
1.
(15 pts) Calculate the percent yield. Show your work.
Reactant
Product
9-fluorenone
9-fluorenol
Mass .210
0.198
MW
180.20 g/mol
182.22 g/mol
Moles 0.001165
0.0009220
Since one mole of reactant yields one mole of product:
Percent Yield = (mole product /mole reactant) x 100 79.141 %
2.
(5 pts) Calculate the R
f
values for the spots on the TLC plate used for testing solvents. Only calculate for spots on plate showing best separation.
3.
(5 pts) Calculate the R
f
values for the spots on the TLC plate showing reaction progress. Comment on whether your TLC showed that your reaction was complete or not.
4.
(20 pts, 10 pts for specifically explaining how each type of data supports claim) Was your synthesis of cyclohexanol succussful? Explain. Use your FTIR, and melting point data as evidence in your explanation. Remember that you need to be specific when using data as
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
evidence of your claim of success or lack of success. If you were unsuccessful, make a specific suggestion for what you would do differently to get better results. The FTIR test matches what we can expect from the product, with a peak just over 3000, and peaks at 1500, 1000, 700. The peak at 3000 is indicating an O-H stretch. The melting point was also what we expect from the product, so in the end this lab was successful.
Related Documents
Related Questions
The solvent level in the development chamber should be above the level of the spotted compounds on the TLC plate.
Group of answer choices
True
False
arrow_forward
DATA REPORT FORM
Procedure A: Ink Analysis by Paper Chromatography
1. Attach the chromatography paper results here.
Name
2. Calculate the Rf value for each ink/marker sample. If there are more than one spot in the
sample, calculate and list Rf for all components.
Procedure B: Identification of Unknown Analgesic Drugs
1. Sketch the best results of the TLC plate here, including unknown sample and known
compounds.
11
arrow_forward
Peak
Retention Time (minutes)
Area
1.201
136501204
acetone
2.011
1253056
toluene
ortho-product
para-product
3.201
8340750
3.350
14890645
a) What was the relative percent yield of the ortho-product?
b) What was the relative percent yield of the para-product?
c) What was the relative percent yield of the product?
arrow_forward
6) You are given a mixture of organic compounds suspected of containing various amines (e. g.
4-chloroaniline). What is the best way to quickly separate these amines from the other organic
compounds?
a) Perform a fractional distillation on the mixture.
b) Benchtop silica gel column chromatography.
c) Dissolve the mixture in an organic solvent and treat the solution with aqueous HCI.
d) Dissolve the mixture in an organic solvent and treat the solution with aqueous NaOH.
arrow_forward
Separation of Amino Acids by Thin Layer Chromatography Lab Questions. Please see photos and answer the questions relating to the images from #10. Thank you!
arrow_forward
In HPLC, why is purging being done before analysis of samples. Outline the procedure on how purging is performed.
arrow_forward
What is the result of applying too much sample to the TLC plate?
Select one:
Some of the sample moves down instead of up
Reduced separation between the spots
O The sample moves past the solvent front
O The spot does not leave the origin
O The sample leeches out into the elution solvent
arrow_forward
! (give detail reason for your correct choice)
arrow_forward
A thermal conductivity detector (TCD) is used
in
a) HPLC
b) GC
c) size exclusion chromatography
d) capillary electrophoresis
arrow_forward
Question attached :)
arrow_forward
ve
After performing a reaction a TLC plate was run to identify the product. Below is the completed
TLC plate. In lane A are the starting materials. In lane B is the sample taken after the reaction was
complete. Did this reaction go to completion? Defend your answer with the TLC results.
Edit View Insert Format Tools Table
12pt Paragraph BIUA
V
>
2 T²:
arrow_forward
There were 2 spots on the TLC that did not match up with any of the standards. What were the Rf values of these spots? Identify what these chemical species might be and draw their structures.
Solvent was 3:1:1 n-butanol/acetic acid/water.
First plate is TLC plate 1. Second plate is TLC plate 2.
arrow_forward
How you can improve resolution in HPLC analysis
arrow_forward
a quick answer is good?
arrow_forward
what is the purpose of TLC Separation & Analysis of Analgesics?
arrow_forward
Organic Chemistry, Column questions
arrow_forward
I'm doing lab report for thin layer chromatography right now, but I'm struggling with a question about how the polarity affect separation. Please help me answer and explain it. Thank you so much!
arrow_forward
What are the elution techniques usually followed in HPLC?
arrow_forward
What is the best solvent system for TLC that would elute this compound? And why is that solvent mixture is appropriate?
arrow_forward
What is the purpose of thin layer chromography lab? What is a hypothesis I can use when conducting a TLC lab and how can that hypothesis be tested?
arrow_forward
Need help with a and b.
A mixture of 1-hexanol, hexane, and 1-chlorohexane is injected on a gas chromatography column.
a) Predict the sequence of retention times indicating which compound will have the shortest, middle, and longest retention time.
b) The sample vial of (a) was not carefully sealed and left partially open for a couple hours. A GC is taken again with only two peaks realized. The first peak to appear has an area of 24 mm2 and the second peak 40 mm2. What mole% of each compound (specify the compound name) is most likely present?
arrow_forward
1. Which property of compounds is responsible for the separation in a TLC? Explain with an example.2. How does the separation occur during a TLC? (Hints: TLC plate and silica layer)
arrow_forward
What is the probable cause of the sample streaking across the TLC plate from origin to solvent front.a. Too much sample
b. Too little sample
C. A developing solvent that is too polar
d. A developing solvent that is too non polar
arrow_forward
Can you help me answer these questions?
arrow_forward
SEE MORE QUESTIONS
Recommended textbooks for you

EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Related Questions
- The solvent level in the development chamber should be above the level of the spotted compounds on the TLC plate. Group of answer choices True Falsearrow_forwardDATA REPORT FORM Procedure A: Ink Analysis by Paper Chromatography 1. Attach the chromatography paper results here. Name 2. Calculate the Rf value for each ink/marker sample. If there are more than one spot in the sample, calculate and list Rf for all components. Procedure B: Identification of Unknown Analgesic Drugs 1. Sketch the best results of the TLC plate here, including unknown sample and known compounds. 11arrow_forwardPeak Retention Time (minutes) Area 1.201 136501204 acetone 2.011 1253056 toluene ortho-product para-product 3.201 8340750 3.350 14890645 a) What was the relative percent yield of the ortho-product? b) What was the relative percent yield of the para-product? c) What was the relative percent yield of the product?arrow_forward
- 6) You are given a mixture of organic compounds suspected of containing various amines (e. g. 4-chloroaniline). What is the best way to quickly separate these amines from the other organic compounds? a) Perform a fractional distillation on the mixture. b) Benchtop silica gel column chromatography. c) Dissolve the mixture in an organic solvent and treat the solution with aqueous HCI. d) Dissolve the mixture in an organic solvent and treat the solution with aqueous NaOH.arrow_forwardSeparation of Amino Acids by Thin Layer Chromatography Lab Questions. Please see photos and answer the questions relating to the images from #10. Thank you!arrow_forwardIn HPLC, why is purging being done before analysis of samples. Outline the procedure on how purging is performed.arrow_forward
- What is the result of applying too much sample to the TLC plate? Select one: Some of the sample moves down instead of up Reduced separation between the spots O The sample moves past the solvent front O The spot does not leave the origin O The sample leeches out into the elution solventarrow_forward! (give detail reason for your correct choice)arrow_forwardA thermal conductivity detector (TCD) is used in a) HPLC b) GC c) size exclusion chromatography d) capillary electrophoresisarrow_forward
- Question attached :)arrow_forwardve After performing a reaction a TLC plate was run to identify the product. Below is the completed TLC plate. In lane A are the starting materials. In lane B is the sample taken after the reaction was complete. Did this reaction go to completion? Defend your answer with the TLC results. Edit View Insert Format Tools Table 12pt Paragraph BIUA V > 2 T²:arrow_forwardThere were 2 spots on the TLC that did not match up with any of the standards. What were the Rf values of these spots? Identify what these chemical species might be and draw their structures. Solvent was 3:1:1 n-butanol/acetic acid/water. First plate is TLC plate 1. Second plate is TLC plate 2.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT

EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT