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The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction
Fall 2022
Lab 6: NBS Bromination Lab Report
Item
Points
Out of
Format
3
Title & Abstract
1
Introduction
4
Results & Discussion
8
Yield
5
Experimental
5
Conclusion
2
References
2
TOTAL
30
The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction
Tyler Hutcherson, CHEM301L, 007, 10/21/2022
Department of Biology and Chemistry, Liberty University
ABSTRACT:
In this experiment, a reflux
apparatus was used in the process of the
bromination of hydrocinnamic acid. The
product is then isolated by the use of
vacuum filtration. The compound was then
allowed to sit for seven days. It was then
analyzed for impurities by determining its
melting point range. Which was revealed
that it was impure. (57 words)
A reflux apparatus
1
1
The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction
Fall 2022
Lab 6: NBS Bromination Lab Report
■
INTRODUCTION
Hydrocinnamic acid (3-phenylpropanoic acid)
2
is used in many different things, such as soaps,
detergents, and softeners because of its sweet scent. It is also used to preserve the aroma of
different frozen foods and is also added to food to help with the manufacturing and processing of
food.
3
The brominated hydrocinnamic acid (3-Bromo-3-phenylpropanoic acid)
4
can be used to
produce other acids.
5
The bromination was conducted via the use of NBS and AIBN. The NBS
was a reagent used as the brominating agent for selective bromination and it illustrates a radical
bromination reaction. The AIBN was a reagent that was used as the radical initiator for the
bromination reaction.
6
This reaction is shown below in Scheme 1.
Scheme 1.
Bromination of hydrocinnamic acid
Water is used to wash off impurities and dissolves the solute Succimide which is soluble
in water at 1g per .07 ml at boiling point.
7
The product was isolated by using vacuum filtration. It
was then air-dried for 10 minutes. To determine its purity its melting point range was analyzed.
The range was 128 – 131.3 °C. This melting point range is lower than the literature value of the
melting point range of 135 – 138 °C. This means the compound was impure. When a compound
has impurities, it will melt at a lower temperature.
In their research Kauffman, R.F, and Palkowitz A.D, used 12.35g in 300ml of
dichloromethane and added 3.2ml of bromine dropwise to a solution of hydrocinnamic acid. The
mixture was illuminated for 15 minutes then stirred for 15 minutes and concentrated. The residue
was triturated with hexanes and ether and yielded 14.7g (78%).
8
The experiment which was
conducted in the lab produced a yield of 85%. The reactions were similar however there were
key differences. The compound was not stirred for as long and then placed on a hot water bath.
Then cooled with ice-cold water and then isolated with vacuum filtration. (316 words)
■
RESULTS AND DISCUSSION
Yield and Appearance
The solid had an appearance that looked similar to spheres and powder. The solid had an off-
white and yellow color. The reaction produced 2.720g (85% yield) of brominated hydrocinnamic
acid which was recovered from the reaction and .007g were produced after sublimation.
The reaction had an atom economy of .698 and a reaction efficiency of 59.33%.
Melting Point
The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction
Fall 2022
Lab 6: NBS Bromination Lab Report
The melting point range of the brominated hydrocinnamic acid that was produced was 128 –
131.3 °C. The literature value of the melting point range is 135 – 138 °C.
The product is impure, this is seen because it had a melting point range of 128 – 131.3 °C
compared to the literature value of 135 – 138 °C has a difference greater than 2 °C.
The reaction that was conducted in the lab had a yield of 85% and
Kauffman, R.F, and
Palkowitz A.D, had a yield of 78%
. The lab experiment had an atom economy of .698 and a
reaction efficiency of 59.33%. Whereas Kauffman had an atom economy .739 and a reaction
efficiency of 57.6%. The lab experiment that was conducted was more successful since it had a
higher yield and slightly higher reaction efficiency.
■
EXPERIMENTAL SECTION
The hydrocinnamic acid was produced by Acros Organics and had a purity of 99%. NBS
was produced by Arcos Organics and had a purity of 99%. AIBN has been provided by
Instructor. Acetic acid (glacial) was produced by Alfa Aesar and had a purity of 99%. A hot water
bath was used and heated to 85 °C over 45 minutes.
3-Bromo-3-phenylpropanoic acid
: A reflux apparatus was set up and used to brominate
the hydrocinnamic acid. 3.206 grams of brominated hydrocinnamic acid (.014 moles) was
synthesized by adding NBS (.014 moles) to brominate the hydrocinnamic acid (.014 moles) and
then added .30 mg of AIBN (.00018 moles). The compound was stirred at room temperature for
3 minutes. It was then heated on a hot water bath for 45 minutes at approximately 85 °C.
Throughout the reaction, several color changes occurred. At the beginning of the 45-minute time
period, it was bright yellow, it then turned bright orange, then to a dark orange, then finally
yellow and transparent. The initial temperature was 75 °C and the final temperature was 82 °C. It
was then cooled for 3 minutes. An ice-cold water bath was set up and the solids were isolated
using vacuum filtration. The crystals were washed with ice-cold water. The product was then
allowed to dry for 10 minutes.
■
CONCLUSION
The reaction was successful with a yield of 85% however the reaction was impure. If the
experiment was continued and run again with the previous product, the product would most
likely be purer. Even though the impurities are present the reaction overall was a success.
■
REFERENCES
(1)
Safety in academic chemistry laboratories students
https://chemistry.unt.edu/sites/default/files/users/owj0001/SMALL
%20ACS_safety_chemistry_laboratories_2017.pdf
(Accessed 10/24/22)
(2) SciFinder:
3-Phenylpropanoic acid
https://scifindern.cas.org/searchDetail/substance/63569979555b613272e69c61/substance
Details
(Accessed 10/24/22)
Your preview ends here
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The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction
Fall 2022
Lab 6: NBS Bromination Lab Report
(3
) Metabocard for Hydrocinnamic acid:
https://hmdb.ca/metabolites/HMDB0000764
(10/24/22)
(4)
Scifinder:
3-Bromo-3-phenylpropanoic acid
https://scifinder-
n.cas.org/searchDetail/substance/63569a3b555b613272e6a701/substanceDetails
(Accessed
10/24/22)
(5)
LookChem:
https://www.lookchem.com/3-Bromo-3-phenylpropionic-Acid/
(10/24/22)
(6)
Radical Polymerization. College of Saint Benedict/Saint John’s University. Collegeville,
MN (2021, September 12).
https://chem.libretexts.org/@go/page/238858
(Date Accessed
10/23/22)
(7) Wiley Online Library (Succimide):
https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rs126
( Accessed 10/23/2022)
(8)
Kauffman, R.F ., and Palkowitz, A.D,
"Treatment of congestive heart failure with growth
hormone secretagogues." U.S. Patent No. 6,329,342. 11 Dec. 2001.
https://worldwide.espacenet.com/patent/search/family/022002400/publication/WO9908697A1?
q=WO9908697A1
(Accessed 10/23/22)
This work is my own work and all help or outside sources have clearly been marked
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estion 21 of 34 >
Complete this reaction of a carboxylic acid with a strong base.
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Incorrect
Insert charges where appropriate for this generic carboxylic acid salt.
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2.
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HW 8
e- CHE 124A - Spring21 - SMITH > Activities and Due Dates > HW 8
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O Attempt 10
< 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
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Learning Target 10
Criteria for satisfactory score
Calculations must be without errors. The diagram must satisfy all listed conditions.
Tasks
1. The reaction below shows radical-mediated halogenation of hydrocarbons. Determine whether the net reaction is
exo- or endothermic by calculating AH for each step and for the net reaction?
(1)
H3C-CH3
F'
H3C-CH, +
H-F
Bond
BDE (kJ/mol)
F-F
157
H,C-CH2
F-F
H3C-CH,F
F'
Cl-CI
243
+
Br-Br
193
I-I
151
H-F
569
H-CI
432
H-Br
366
H-I
299
C=C (x)
272
C-F
481
C-CI
350
С-Br
284
C-I
209
CH;CH,-H
423
Figure 7: Multi-step reaction sequence
2. Draw the energy diagram for a reaction with the following paramaters:
• The reaction has 2 steps
• The overall reaction is not spontaneous.
• The first step is a slow equilibrium (K = 1).
• The second step is faster than the first step.
Label substrate, product, transition states, and intermediates on your diagram.
REACTION PROGRESS
Figure 8: Reaction energy diagram
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6. Give a reaction mechanism for the formation of a hemiacetal starting material below.
the final product.
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None
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V a reaction in which all bond-breaking and bond-forming occurs at the same time
a reaction in which bond forming occurs first
O a substitution reaction
QUESTION 28
Which of the fallowing is the rate equation for the following SN2 reaction?
CN
Br
NaCN
+ NaBr
O Rate = kl1-bromopropane]
O Rate = kINaCN)
Rate = k1-bromopropane] [NACN]
Rate = k[1-bromopropane]2
O Rate = k[1-bromopropane]2 [NACNJ2
QUESTION 29
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Question 2
The reaction of sodium ethoxide with iodoethane to form diethyl ether is classified as:
O an electrophilic substitution
O a nucleophilic substitution
O a radical substitution
O an electrophilic addition
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Experiment
1
2
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(CH3)3CBr + OH → (CH3)3COH + Br
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b) Write the rate law.
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need to use the information you calculated in step c in order to first calculate
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O Attempt 2
Complete this reaction of a carboxylic acid with a strong base.
reaction: C,H,COOH + NAOH C,H, + COO¯Na* + H,0
Incorrect
Insert charges where appropriate for this generic carboxylic acid salt.
Na
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27. Which of the following compounds is a tautomer of the following compound?
HO.
HO.
a.
b.
OH
C. Both a and b
d. Neither a nor b
28. NaBH4 reduces aldehydes to primary alcohols.
a. True
b. False
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Aspirin can be synthesized from
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catalytie H90,
d183 gimi.
(0.05 mol) according to the reaction
saieylie acid CHO
MW-13812 amal
acetyi chleride CHO.
M 100 0 d
d1.08 gim
anpirie CO,
MW 180.1s gmel
shown.
If 1.0 mol of salicylic acid and 3.0
A) H,SO,
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