How do I calculate the percent yield based on the limiting reactant in this bromination of trans-cinnamic acid reaction? (See attachments for further information)
How do I calculate the percent yield based on the limiting reactant in this bromination of trans-cinnamic acid reaction? (See attachments for further information)
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
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How do I calculate the percent yield based on the limiting reactant in this bromination of trans-cinnamic acid reaction? (See attachments for further information)
0.149 g of trans-cinnamic acid was initial mass of the
1.0 mL of glacial acetic acid (AcOH) was used
1.0 mL of Br2 was used
0.128 g of (2R, 3S)/(2S, 3R)-2,3-dibromo-3-phenylpropanoic acid was the final mas of the product
![transition state for syn-addition
xperiment, the electrophilic addition reaction of trans-cinnamic acid with
d out and the stereochemistry assigned for the resulting product. As describ
c nature of the substituents on the double bond can have a significant i
ectivity that is observed. Here, the starting material contains two substituen
stabilize a positive charge at the benzylic position by resonance, while th
Is to disfavor carbocation formation since it is an electron-withdrawing grou
OH
trans-cinnamic acid
Br₂
ACOH
Br
Br
OH
2,3-dibromo-3-phenylpropanoic acid
eochemical outcome of the
bromination-syn-addition, trans-addition, or
can be determined based on the melting point of the product. As not
material is achiral and the reaction thus gives a pair of enantiomers (which I
point). One of the possible products is the enantiomeric pair (2R, 3R),
-3-phenylpropanoic acid, which has a melting point of 93.5-95 °C. The
is the enantiomeric pair (2R, 3S)/(2S, 3R)-2,3-dibromo-3-phenylpropanoi
elting point of 202-204 °C. Thus, the syn- and anti-products can be easily di
at impurities such as traces of solvent may lower the experimental meltir
on of several degrees from the literature melting point is acceptable. If
es a mixture of the syn- and anti-isomers, the observed melting point will
ange since it is essentially a mixed melting point. Based on this data, it
a mechanism that is consistent with the observed stereochemistry of the pro](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc62819af-1f81-4d59-bfb3-1ca1702855ed%2F68c15588-d56b-49e3-bb3c-29ed164a1e9a%2Fwi82fjb_processed.jpeg&w=3840&q=75)
Transcribed Image Text:transition state for syn-addition
xperiment, the electrophilic addition reaction of trans-cinnamic acid with
d out and the stereochemistry assigned for the resulting product. As describ
c nature of the substituents on the double bond can have a significant i
ectivity that is observed. Here, the starting material contains two substituen
stabilize a positive charge at the benzylic position by resonance, while th
Is to disfavor carbocation formation since it is an electron-withdrawing grou
OH
trans-cinnamic acid
Br₂
ACOH
Br
Br
OH
2,3-dibromo-3-phenylpropanoic acid
eochemical outcome of the
bromination-syn-addition, trans-addition, or
can be determined based on the melting point of the product. As not
material is achiral and the reaction thus gives a pair of enantiomers (which I
point). One of the possible products is the enantiomeric pair (2R, 3R),
-3-phenylpropanoic acid, which has a melting point of 93.5-95 °C. The
is the enantiomeric pair (2R, 3S)/(2S, 3R)-2,3-dibromo-3-phenylpropanoi
elting point of 202-204 °C. Thus, the syn- and anti-products can be easily di
at impurities such as traces of solvent may lower the experimental meltir
on of several degrees from the literature melting point is acceptable. If
es a mixture of the syn- and anti-isomers, the observed melting point will
ange since it is essentially a mixed melting point. Based on this data, it
a mechanism that is consistent with the observed stereochemistry of the pro
![Data Tables
Table 1-Results from experiment
Mass of Alkene
Mass of Product
Percent Yield Based on Limiting Reactant
(Show calculations in the space below)
Melting Point of Product
11499
•1289
176.3 °C -180.6°C](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc62819af-1f81-4d59-bfb3-1ca1702855ed%2F68c15588-d56b-49e3-bb3c-29ed164a1e9a%2Fvnh1djl_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Data Tables
Table 1-Results from experiment
Mass of Alkene
Mass of Product
Percent Yield Based on Limiting Reactant
(Show calculations in the space below)
Melting Point of Product
11499
•1289
176.3 °C -180.6°C
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