Worksheet 4-Acid Base

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Pennsylvania State University *

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202

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Chemistry

Date

Feb 20, 2024

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6

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1 Worksheet 4-Acid and Base Chemistry For extra practice, please read the book (Chapter 2) and do the following practice problems: Chapter 2 #1-31, 34, 38-49, 50-52, 54, Tutorial pages 65-72 1. For each of the following molecules, determine if it is more or less acidic than ethanol (CH3CH2OH). Then, briefly explain why. Referencing pKa values is not an explanation! Use the trends! Molecule More/Less Acidic than Ethanol Why? CF 3 CH 2 OH CH 3 CH 2 SH CH 3 CH 2 NH2 CH 3 CH 2 CH 3
2 2. Consider cyclohexanol and phenol drawn below. Draw the conjugate bases of each molecule and then explain why cyclohexanol is a weaker acid.
3 3. Put the following compounds in order from weakest acid to strongest acid. Then, explain in words why you ranked the acids in the designated order. Remember, pKa values are not enough to explain! Use the trends! 4. Even though it is usually difficult to remove a proton from a neutral nitrogen atom, the proton on this molecule below (glutarimide) is fairly acidic! Draw the structure of the conjugate base, the two additional resonance contributors, and the resonance hybrid in the indicated boxes.
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4 5. Draw the products of the following acid/base reactions, depict the proton exchange with mechanistic arrows, AND circle the proper reaction arrow to indicate if reactants or products (or neither) are favored at equilibrium. Using our pKa table, write all relevant pKa values (i.e. for the two reactants if available and the conjugate acid). Finally, label the Acid, Base, Conjugate Acid, and Conjugate Base.
5 6. Circle the side of the following reactions where the equilibrium lies in each of the following acid/base reactions. pKa tables may help you but will not be absolute. Briefly explain your reasoning. Remember the 5 things that influence base stability as that is what you will be primarily comparing (the conjugate base on the right versus stability to the original base on the left). The equilibrium will lie to the side of the most stable, less reactive base (the happy chappy).
6
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