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CHEM 324
Organic Reactions
Experiment 57
Using the Chemical Literature in an Organic Synthesis
Jiani He
26380107
Performed Thursday 09/21/2023
Submitted on Thursday 09/28/2023
1.
What is the CAS Registry Number of your target compound? It is 62571-86-2.
2.
Draw its structure.
3.
Give at least one synonym for your compound.
(S)-1-((S)-3-mercapto-2-methylpropanoyl)pyrrolidine-2-carboxylic acid L-Proline, 1-[(2S)-3-mercapto-2-methyl-1-oxopropyl]-
4.
Use SciFinder to locate an article that outlines a multi-step synthetic pathway for making your compound. Provide a printout or photocopy of the first page of the article.
a.
Write out two steps of the reaction giving compound names and their structures.
1
1
: (S)-proline
2
: N-acryloyl-(S)-proline
3
: β-Hydroxy-α-methylene-N-acryloyl-(S)-proline
b.
Provide the reaction conditions.
1
In the first step, an ice-bath was used to cool a stirred solution of 1 (43 mmol, 5 g) in 2 M aqueous potassium hydroxide (52 mmol, 26 mL). Acetone (26 mL) was used to dilute the solution. Over the course of 40 minutes, 2 M aqueous potassium hydroxide (61 mmol, 30 mL) and an acetone solution (26 mL) of acryloyl chloride (48 mmol, 4.34 g) were added simultaneously to the stirred mixture. The reaction was allowed to reach room temperature and react for 3 h, after which the product, 2
, was isolated, purified and characterized. In the second step, 2 (1.89 mmol, 0.472 g) was dissolved in tetrahydrofuran (10 mL), followed by the addition of 5 mL of 40% aqueous formaldehyde (54.28 mmol, 1.63 g). The mixture was sonicated for 48 h before isolation, purification and characterization were performed.
c.
Include amounts of reactants and product yield.
In the first step, the reactants are 5 g of (S)-proline (1.00 eqv) and 4.34 g of acryloyl chloride (1.12 eqv);
the percent yield of this step is 70%.
1
In the second step, the reactants are 0.472 g of (S)-1-
acryloylpyrrolidine-2-carboxylic acid (1.00 eqv) and 1.63 g of formaldehyde (28.72 eqv); the percent yield of this step is 93%.
1
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Related Questions
In this lab you are performing your first organic synthesis and safety information on all the materials you are using must be obtained.
Companies are required to provide material safety data sheets (MSDS) for chemical compounds they sell.
Please examine the MSDS for acetic anhydride, available here. You will find GHS pictograms within the sheet that summarize the
main hazards of this compound. The pictograms are essentially the same as the symbols on WHMIS labels, available here for
reference.
Based on the pictograms, whatare the main hazards for acetic anhydride? Select as many answers as appropriate
Select one or more:
Carcinogen
Gas under pressure
Acute oral or inhalation toxicity
Corrosive
Flammable material
Oxidizing material
Self-reactive substance
arrow_forward
only the questions pls disregard the experiment results thank you
arrow_forward
What is the correct term for the type of reaction shown below?
A Friedel-Crafts Alkylation
B) Friedel-Crafts Acylation
c) Nucleophilic Aromatic Substitution
D) EAS Halogenation
Br
NaNH,
NH3 (liq) -33 C
NH₂
6
arrow_forward
1. Write the structure of the aminal or hemiaminal intermediate and the imine
product formed in the reaction of Acetaldehyde and benzylamine,
C6HSCH2NH2.
2. Write the structure of the hemiaminal intermediate and the enamine
product formed in the reaction of 3-Pentanone and pyrrolidine.
3. Identify the alkene formed in the following reaction
'H.
(CeHs)»P-
4. Predict the principal organic product for the following reaction.
K2Cr2O7
H2SO4, H20
H.
5. What is the expected chemical shift for the aldehyde hydrogen in 'H NMR
and aldehyde carbon in 13C NMR?
arrow_forward
Match column A (common active ingredients of insect repellants) to column
B (IUPAC names).
Column A
Column B
1. Citronellol and Geraniol
a. 6 parts DMP, 2 parts Indalone, and 2 part of
Rutgers 612
b. Six esters (pyrethrins)
2. DEET
3. DMP
c. 1-piperidine carboxylic acid-2(2-
4. 6-2-2
hydroxyethyl)-1-methylpropyl ester
d. 3-(N-acetyl-N-butyl) aminopropionic acid
5. Picaridin
6. Citriodiol
ethyl ester
7. IR-3535
e. butyl-3,3- dihydro-2,2-dimethyl-4-oxo-2H-
pyran-6-carboохуlate
f. para-menthane-3,8-diol
8. Rutgers 612
9. Indalone
g. dimethyl phthalate
10. Pyrethrum
h. 2-ethyl-1,3-hexanediol
i. 3,7-Dimethyloct-6-en-1-ol
j. N, N-diethyl-m-toluamide
arrow_forward
Which of the following correctly describes the
movement of electrons in the reaction of
nucleophile (Nu:) with a carbonyl group?
A) Nu:
B)
Nu:
C) Nu:
D) Nu:
ܤ ܗ
+
+
R
R
R
R
R
V
R
R
R
O:
Nu-
Nu-
Nu
Nu
:Ö:*
¹R
R
:Ö:
"R
R
:Ö:
"R
R
:O:
"R
R
arrow_forward
Question 5
ORC2601/102/0/202
[8]
Using a suitable example (show the movement of electrons with arrows), explain why a
Friedel-Craft acylation of aniline is likely to meet with a disaster.
Total marks [40]
arrow_forward
Following is a retrosynthetic analysis for the anthelmintic (against worms)
diethylcarbamazine.
N.
`NET2
N.
OEt
Me
Me
Diethylcarbamazine
(A)
(2)
OH
MENH,
CI
OEt
Me
OH
Me
Methylamine
Ethylene
(C)
(В)
Ethyl
oxide
chloroformate
Diethylcarbamazine is used chiefly against nematodes, small cylindrical or slender
threadlike worms such as the common roundworm, which are parasitic in animals and
plants. Given this retrosynthetic analysis, propose a synthesis of diethylcarbamazine
from the three named starting materials.
arrow_forward
(neutralisation reaction) use the given guidelines to solve this question
arrow_forward
Emily synthesized acetanilide by stirring aniline and acetic anhydride together in water at 100C. Acetanilide is a solid at room temperature, while everything else is a liquid. Emily noted that while the reaction was running, everything was dissolved and the liquid was a pale orange. Emily allowed the reaction to cool to room temperature and then cooled it in an ice bath. After the slow cooling, a solid appeared.
1. Based only on Emily's observations from this procedure, what solvent does she know will work to recrystallize the acetanilide if needed?
aniline
aqueous ethanol
water
acetic acid
arrow_forward
Emily synthesized acetanilide by stirring aniline and acetic anhydride together in water at 100C. Acetanilide is a solid at room temperature, while everything else is a liquid. Emily noted that while the reaction was running, everything was dissolved and the liquid was a pale orange. Emily allowed the reaction to cool to room temperature and then cooled it in an ice bath. After the slow cooling, a solid appeared.
1. Based only on Emily's observations from this procedure, what solvent does she know will work to recrystallize the acetanilide if needed?
aniline
aqueous ethanol
water
acetic acid
2. According to PubChem, acetanilide melts at 114°C. Emily measured a melting point of 96 - 104°C for the solid they collected. What can be said about this solid?
- Melting point does not indicate whether a sample is pure or not
- The experimental range is narrow and close to the literature value, suggesting it is not completely pure
- The experimental range is narrow…
arrow_forward
37 of 70 04:37 / 01:30:00
Below organic compound is
named as (E)-3-(4-
hydroxyphenyl)prop-2-enoic acid.
If it is correct, type True. If not,
type the correct nomenclature.
HO,
Answer:
arrow_forward
What are the three[3] detection tests of elements in organic compounds that you appreciated most, and give the method on how to determine the element?
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What sequence of steps can comvert benzene into 4-isobutylacetophenone
arrow_forward
questions 1,2, and 3 only pls disregard the experiment results
arrow_forward
FTIR Tables
List position (cm) & functional group 4.
5.
3.
7.
6.
1.
2.
arrow_forward
A student was trying to treat an alcohol with PCC and when they took the IR below they wanted to see if the product had formed. What evidence supports the suspicions that the product did form?
arrow_forward
Answer the questions
arrow_forward
Can someone please help me find what chemical this is? I know its an aldehyde but Im really lost.
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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
Be sure to answer all parts.
Give the systematic name for SnBr2.
(select)
V (select) V (select)
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None
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ab
scms/mod/flcn/view.php?id%315420208
Christin Jimmersor
HW 8
e- CHE 124A - Spring21 - SMITH > Activities and Due Dates > HW 8
O Resources
Give Up?
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O Assignment Score:
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< Question 20 of 34
A carboxylic acid reacts with water to form a carboxylate ion and H,O+. Complete the reaction.
reaction: CH,CHOHCOOH + H,0 = CH,CHOHCOO¯ + H,o+
Write the IUPAC name of the carboxylate ion formed in the reaction.
IUPAC name: 2-Hydroxypropoate
Incorrect
arrow_forward
25. NMR spectra (Figures a, b, c and d) of four isomers are shown. with formula Cl0HuOr Their infrared spectra show strong bands close to 1735 cm'1, do not interpret the aromatic proton region between 7.0 and 7.5 ppm, except to determine the number of protons attached to the aromatic ring. Draw as structures of compounds.
arrow_forward
Create a visualization that explains the process of synthesizing your chosen molecule (Melatonin) in a maximum of
five steps. Your visualization should show each reaction involved, and provide a brief explanation of what is
happening in each reaction. Some reaction types have been given names that you can use to describe the synthesis.
You may also want to show how the electrons are moved between the reactive groups to make or break covalent
bonds. You should also explain the role of your chosen instrument (Nuclear Magnetic Resonance (NMR)
spectroscopy) in verifying each step in your synthesis of the different intermediate product formed before the final
product of the entire process. This explanation should be for a non-scientific audience, as this visualization will be a
handout that you will be giving out to the audience as part of the pitch you will be giving next week.
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Related Questions
- In this lab you are performing your first organic synthesis and safety information on all the materials you are using must be obtained. Companies are required to provide material safety data sheets (MSDS) for chemical compounds they sell. Please examine the MSDS for acetic anhydride, available here. You will find GHS pictograms within the sheet that summarize the main hazards of this compound. The pictograms are essentially the same as the symbols on WHMIS labels, available here for reference. Based on the pictograms, whatare the main hazards for acetic anhydride? Select as many answers as appropriate Select one or more: Carcinogen Gas under pressure Acute oral or inhalation toxicity Corrosive Flammable material Oxidizing material Self-reactive substancearrow_forwardonly the questions pls disregard the experiment results thank youarrow_forwardWhat is the correct term for the type of reaction shown below? A Friedel-Crafts Alkylation B) Friedel-Crafts Acylation c) Nucleophilic Aromatic Substitution D) EAS Halogenation Br NaNH, NH3 (liq) -33 C NH₂ 6arrow_forward
- 1. Write the structure of the aminal or hemiaminal intermediate and the imine product formed in the reaction of Acetaldehyde and benzylamine, C6HSCH2NH2. 2. Write the structure of the hemiaminal intermediate and the enamine product formed in the reaction of 3-Pentanone and pyrrolidine. 3. Identify the alkene formed in the following reaction 'H. (CeHs)»P- 4. Predict the principal organic product for the following reaction. K2Cr2O7 H2SO4, H20 H. 5. What is the expected chemical shift for the aldehyde hydrogen in 'H NMR and aldehyde carbon in 13C NMR?arrow_forwardMatch column A (common active ingredients of insect repellants) to column B (IUPAC names). Column A Column B 1. Citronellol and Geraniol a. 6 parts DMP, 2 parts Indalone, and 2 part of Rutgers 612 b. Six esters (pyrethrins) 2. DEET 3. DMP c. 1-piperidine carboxylic acid-2(2- 4. 6-2-2 hydroxyethyl)-1-methylpropyl ester d. 3-(N-acetyl-N-butyl) aminopropionic acid 5. Picaridin 6. Citriodiol ethyl ester 7. IR-3535 e. butyl-3,3- dihydro-2,2-dimethyl-4-oxo-2H- pyran-6-carboохуlate f. para-menthane-3,8-diol 8. Rutgers 612 9. Indalone g. dimethyl phthalate 10. Pyrethrum h. 2-ethyl-1,3-hexanediol i. 3,7-Dimethyloct-6-en-1-ol j. N, N-diethyl-m-toluamidearrow_forwardWhich of the following correctly describes the movement of electrons in the reaction of nucleophile (Nu:) with a carbonyl group? A) Nu: B) Nu: C) Nu: D) Nu: ܤ ܗ + + R R R R R V R R R O: Nu- Nu- Nu Nu :Ö:* ¹R R :Ö: "R R :Ö: "R R :O: "R Rarrow_forward
- Question 5 ORC2601/102/0/202 [8] Using a suitable example (show the movement of electrons with arrows), explain why a Friedel-Craft acylation of aniline is likely to meet with a disaster. Total marks [40]arrow_forwardFollowing is a retrosynthetic analysis for the anthelmintic (against worms) diethylcarbamazine. N. `NET2 N. OEt Me Me Diethylcarbamazine (A) (2) OH MENH, CI OEt Me OH Me Methylamine Ethylene (C) (В) Ethyl oxide chloroformate Diethylcarbamazine is used chiefly against nematodes, small cylindrical or slender threadlike worms such as the common roundworm, which are parasitic in animals and plants. Given this retrosynthetic analysis, propose a synthesis of diethylcarbamazine from the three named starting materials.arrow_forward(neutralisation reaction) use the given guidelines to solve this questionarrow_forward
- Emily synthesized acetanilide by stirring aniline and acetic anhydride together in water at 100C. Acetanilide is a solid at room temperature, while everything else is a liquid. Emily noted that while the reaction was running, everything was dissolved and the liquid was a pale orange. Emily allowed the reaction to cool to room temperature and then cooled it in an ice bath. After the slow cooling, a solid appeared. 1. Based only on Emily's observations from this procedure, what solvent does she know will work to recrystallize the acetanilide if needed? aniline aqueous ethanol water acetic acidarrow_forwardEmily synthesized acetanilide by stirring aniline and acetic anhydride together in water at 100C. Acetanilide is a solid at room temperature, while everything else is a liquid. Emily noted that while the reaction was running, everything was dissolved and the liquid was a pale orange. Emily allowed the reaction to cool to room temperature and then cooled it in an ice bath. After the slow cooling, a solid appeared. 1. Based only on Emily's observations from this procedure, what solvent does she know will work to recrystallize the acetanilide if needed? aniline aqueous ethanol water acetic acid 2. According to PubChem, acetanilide melts at 114°C. Emily measured a melting point of 96 - 104°C for the solid they collected. What can be said about this solid? - Melting point does not indicate whether a sample is pure or not - The experimental range is narrow and close to the literature value, suggesting it is not completely pure - The experimental range is narrow…arrow_forward37 of 70 04:37 / 01:30:00 Below organic compound is named as (E)-3-(4- hydroxyphenyl)prop-2-enoic acid. If it is correct, type True. If not, type the correct nomenclature. HO, Answer:arrow_forward
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SEE MORE QUESTIONS
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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