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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)

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)

Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter4: Chemical Reactions
Section: Chapter Questions
Problem 4.75P
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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 alkene

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
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
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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