EBK LABORATORY MANUAL FOR GENERAL, ORGA
3rd Edition
ISBN: 9780321918352
Author: Timberlake
Publisher: YUZU
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Chapter 4, Problem 4.74AP
Determine whether each of the following is the cis or the trans stereoisomer:
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Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Synthesis of ZybanⓇ:
1. Write a mechanism for the bromination of m-chloropropiophenone.
Br₂
CH2Cl2
Cl
Br
2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks).
3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Chapter 4 Solutions
EBK LABORATORY MANUAL FOR GENERAL, ORGA
Ch. 4 - Prob. 4.1PPCh. 4 - Prob. 4.2PPCh. 4 - Prob. 4.3PPCh. 4 - Draw a skeletal structure for ethane, C2H6. Do you...Ch. 4 - Prob. 4.5PPCh. 4 - Prob. 4.6PPCh. 4 - Draw a Lewis structure for each of the following...Ch. 4 - Draw a Lewis structure for each of the following...Ch. 4 - Prob. 4.9PPCh. 4 - Prob. 4.10PP
Ch. 4 - Prob. 4.11PPCh. 4 - Prob. 4.12PPCh. 4 - Write the condensed structure for the...Ch. 4 - Write the condensed structure for the...Ch. 4 - Write the skeletal structure for the alkane shown:...Ch. 4 - Write the skeletal structure for the alkane shown:...Ch. 4 - Identify the family of hydrocarbon present in the...Ch. 4 - Identify the family of hydrocarbon present in the...Ch. 4 - Identify all the functional groups present in the...Ch. 4 - Prob. 4.20PPCh. 4 - The most prevalent fatty acid in coconut oil is...Ch. 4 - The most common fatty acid found in animals is...Ch. 4 - Draw the condensed structural formula for each of...Ch. 4 - Give the correct name for each of the following...Ch. 4 - Draw the skeletal structure for each of the...Ch. 4 - Prob. 4.26PPCh. 4 - Prob. 4.27PPCh. 4 - Prob. 4.28PPCh. 4 - Prob. 4.29PPCh. 4 - Prob. 4.30PPCh. 4 - Determine the relationship between each of the...Ch. 4 - Determine the relationship between each of the...Ch. 4 - Determine if each of the following cycloalkanes or...Ch. 4 - Determine it each of the following cycloalkanes or...Ch. 4 - Mark the chiral centers in the following...Ch. 4 - Mark the chiral centers in the following...Ch. 4 - Convert each of the Lewis structures shown into a...Ch. 4 - Convert each of the Lewis structures in Problem...Ch. 4 - Prob. 4.39APCh. 4 - Prob. 4.40APCh. 4 - Convert the skeletal structures shown to condensed...Ch. 4 - Convert the skeletal structures shown to condensed...Ch. 4 - Prob. 4.43APCh. 4 - Prob. 4.44APCh. 4 - Alkanes are also referred to as saturated...Ch. 4 - Are alkanes considered polar or nonpolar...Ch. 4 - Give the skeletal structure and name of the...Ch. 4 - Give the skeletal structure and name of the...Ch. 4 - Name the following straight-chain alkanes or...Ch. 4 - Name the following straight-chain alkanes or...Ch. 4 - Explain the structural difference between a...Ch. 4 - Prob. 4.52APCh. 4 - Identify all of the functional groups in each of...Ch. 4 - Identify all of the functional groups in each of...Ch. 4 - Prob. 4.55APCh. 4 - Prob. 4.56APCh. 4 - Prob. 4.57APCh. 4 - Draw skeletal structures for each of the following...Ch. 4 - Prob. 4.59APCh. 4 - Prob. 4.60APCh. 4 - Prob. 4.61APCh. 4 - Prob. 4.62APCh. 4 - Prob. 4.63APCh. 4 - Prob. 4.64APCh. 4 - Prob. 4.65APCh. 4 - Prob. 4.66APCh. 4 - How many structural isomers are possible for the...Ch. 4 - Prob. 4.68APCh. 4 - Prob. 4.69APCh. 4 - Prob. 4.70APCh. 4 - For each of the following compounds, indicate...Ch. 4 - Prob. 4.72APCh. 4 - Determine whether each of the following is the cis...Ch. 4 - Determine whether each of the following is the cis...Ch. 4 - Prob. 4.75APCh. 4 - Prob. 4.76APCh. 4 - Mark the chiral centers in the following...Ch. 4 - Mark the chiral centers in the following...Ch. 4 - Prob. 4.79APCh. 4 - Prob. 4.80APCh. 4 - Prob. 4.81CPCh. 4 - Prob. 4.82CPCh. 4 - Prob. 1IA.1QCh. 4 - Prob. 1IA.2QCh. 4 - Prob. 1IA.3QCh. 4 - Prob. 1IA.4QCh. 4 - Prob. 1IA.5QCh. 4 - Prob. 1IA.6QCh. 4 - Prob. 1IA.7QCh. 4 - Prob. 1IA.8QCh. 4 - Prob. 1IA.9QCh. 4 - Prob. 1IA.10QCh. 4 - Prob. 1IA.11QCh. 4 - Prob. 2IA.1QCh. 4 - Prob. 2IA.2QCh. 4 - Prob. 2IA.3QCh. 4 - Prob. 2IA.4QCh. 4 - Prob. 2IA.5QCh. 4 - What is the molecular shape (geometry) of the...Ch. 4 - Prob. 2IA.7QCh. 4 - Prob. 1ICCh. 4 - Prob. 2ICCh. 4 - Prob. 3ICCh. 4 - Prob. 4IC
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