Chapter 2: 37P (page 139)
Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do.
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Chapter 2: 37P (page 139)
Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do.
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The pKa of ascorbic acid (vitamin C, page 9) is 4.17 , showing that it is lightly more acidic than acetic acid (CH3COOH,pKa =4.74) .
(a)Show four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.
(b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.
(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH ) group
Predict which member of each pair is more soluble in water. Explain your prediction.
(a)

(b)

(c)

(d)

(e)

(f)

The preceding equation for the protonation of acetamide shows a hypothetical product that is not actually formed. When acetamide is protonated by a strong enough acid, it does not protonate on nitrogen, but at different basic site. Draw the structure of the actual conjugate acid of acetamide, and explain (resonance) why protonation occurs where it does rather than on nitrogen. Calculate the pKa of this conjugate acid.
The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.
Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.
(a)

(b)

(c)

(d)

(e)
(f)

(g)

(h)

(i)

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