A Small Scale Approach to Organic Laboratory Techniques
4th Edition
ISBN: 9781305799875
Author: Donald L. Pavia; George S. Kriz; Gary M. Lampman
Publisher: Cengage Learning US
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Chapter 16, Problem 2Q
Interpretation Introduction
Interpretation:
The commercial method for the production of absolute ethanol needs to be explained.
Concept Introduction:
Ethanol is an organic compound with chemical formula
Carbohydrates like disaccharides such as sucrose and maltose are used to prepare this alcohol. Disaccharides are composed of two saccharides which are bonded with glycosidic linkage. Sucrose is composed of one glucose and one fructose molecules whereas maltose is composed of two glucose units.
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Sodium Borohydride Reduction (continued on the next page):
1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number.
?
(1) NaBH
(2) acid
(1) NaBD4
(2) acid
?
2.
In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is
generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question
# 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z).
3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an
excess of butyrophenone.
4.
+ NaBH4
OH
(after workup with dilute
HCI)
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?
Aspirin from Wintergreen:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4.
3. Calculate the exact monoisotopic mass of aspirin showing your work.
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 Ibuprofen-Part 1:
1.
What characteristic absorption band changes would you expect in the IR spectrum on going from p-isobutylacetophenone to
1-(4-isobutylphenyl)-ethanol and then to 1-(4-isobutylphenyl)-1-choroethane as you did in the experiment today? Give
approximate wavenumbers associated with each functional group change.
Given that the mechanism of the chlorination reaction today involves formation of a benzylic carbocation, explain why the
following rearranged product is not formed.
محرم محمد
3. Why do we use dilute HCl for the first step of the reaction today and concentrated HCI for the second step?
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 16 Solutions
A Small Scale Approach to Organic Laboratory Techniques
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