Chapter 2: 38P (page 139)
Rank the following species in order of increasing basicity. Explain your reasons for ordering them as you do.
Chapter 2: 38P (page 139)
Rank the following species in order of increasing basicity. Explain your reasons for ordering them as you do.
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Get started for freeEthanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.
(a) Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. In each case, show the equation for the reaction with a generic base to give the conjugate base.
(b) Rank ethanol, methylamine, and acetic acid in decreasing order of basicity. In each case, show the equation for the reaction with a generic acid to give the conjugate acid.
The N-F bond is more polar than N-H bond, but NF3 has smaller dipole moment than NH3. Explain the curious result.
NH3: µ= 1.5 D, NF3: µ= 0.2D
Consider the following proposed Bronsted-Lowry acid-base reactions. In each case, draw the products of a transfer of the most acidic proton on the acid to the most basic site on the base. Use Appendix 4 to find the pKa values for the acids and the pKb values for the bases. Then determine which side of the reaction is favored, either reactants of products.
(a)
(b)
(c)
(d)
(e)
(f)
Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.
(a)
In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reaction. Draw any nonbonding electrons to show how they participate in the reactions.
(a)
(b)
(c)
(d)
(e)
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