Draw the organic product of the Lewis acid-base reaction shown below. Include all lone pairs and charges as appropriate. draw as a skeletal structure Draw the organic product of the Lewis acid-base reaction shown below. Include all lone pairs and charges as appropriate. BF3

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.

As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.

Phenol (shown below) has a pKa10 . a. Based on pKa data, is phenol a stronger or weaker acid than an ordinaryalcohol (e.g.. CH3OH ) or water? b. Draw the conjugate base of phenol (called phenoxide) including allimportant resonance structures. c. Construct an explanation for why phenol is a stronger acid than anordinary alcohol. (You may want to consider first why phenoxide is lowerin PE than methoxide (RO) or hydroxide (HO) .

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Arrange the molecules and ions in   set in order of increasing acidity (from least acidic to most acidic).

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Which of compounds A and B is the stronger base? Why? A NH N.

Rank 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 V

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