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 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.
Ozone has a dipole moment of 0.53 D. Carbon dioxide has a dipole moment of zero, even though C-O bonds are more polar than O-O bonds. Explain this apparent contradiction.
Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?
(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

(k)

(l)

Consider each pair of bases, and explain which one is more basic. Draw their conjugate acids, and show which one is a stronger acid.
(a)

(b)

(c)

(d)

N-Methylpyrrolidine has a boiling point of, and piperidine has a boiling point of.

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