10. Draw the conjugate base of each acid below. Then draw all resonance that stabilizes the conjugate bases. Finally rank the acids (not the conjugate bases) from lowest to highest pKa. 요요애 요요
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- The following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)For the previous four questions, label each molecule that appears in the question or your answer asstrong acid, strong base, weak acid, or weak base.
- 2. Draw the most stable conjugate base and most stable conjugate acids for the following compounds. H₂N F2 Но ОН двоен дел одели по ОН H -CO2H ОН8) The compound below has 3 N atoms and each can potentially serve as a base. However, one N atom is more basic than the others. a) Circle the most basic electron pair. b) Draw the conjugate acid after it has been protonated. c) Explain your decision by describing the relative stability of the conjugate acid. CH,—NH—C NH NH₂A) for each compound show its conjugate base. lone pairs have been left out. B) rank the conjugate base in the order you would predict, from most to least stable. C) rank the original compounds in order, from strongest to weakest acid.
- Rank the following in order of decreasing basicity. You may use analogous structures in a table of acidity constants to guide your reasoning. Be sure to answer all parts. Drag each item to the correct box. Most basic ☐ ? de Least basic5. In each pair, which species is a stronger base? Justify your answer. FDraw the products of the following acid/base reactions, depict the proton exchange with electron-pushing arrows, AND circle the proper reaction arrow to indicate if reactants or products (or neither) are favoured at equilibrium. Using the provided 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.
- 2. a) For each compound show its conjugate base. Lone pairs have been left out but are assumed to be t Show all valence electrons. Show any resonance structures if applicable. b) Rank the conjugate bases in the order you would predict, from most stable to least stable. c) Rank the original compounds in order, from strongest acid to weakest acid. OH Br OH OH OHRank the following bases in order of decreasing basicity. HCEC: A B D CHỊCH, II E III > | > V > || > IV (C) V> I > III > II > IV III > V > IV > I>|| III > IV>II>V>I |V > || > | > ||I > V CH3CH2 III H₂N: IV H₂C=CH VWhich of the following bases has a conjugate acid with the smallest pKa? Select one: O (CH_CH,CH),N O NH, O CH,CH,CH,NH, O (CH,CH,CH,), NH
