Chapter 19: Q38P (page 1029)
Predict the products of the following reactions:
(a)
(b)
(c)

(d)
(e)

(f)
(g)

(h)

(i)

(j)
(k)

(l)

Short Answer
(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

(k)

(l)

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Chapter 19: Q38P (page 1029)
Predict the products of the following reactions:
(a)
(b)
(c)

(d)
(e)

(f)
(g)

(h)

(i)

(j)
(k)

(l)

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

(k)

(l)

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We have considered nucleophilic aromatic substitution of pyridine at the 2-position and 3-position but not the at the 4-position. Complete the three possible cases by showing the mechanism for the reaction of methoxide ion with 4-chloropyridine. Show how the intermediate is stabilized by delocalization of the charge onto the nitrogen atom.
Rank each set of compounds in order of increasing basicity
(a) NaOH, NH3, CH3NH2, Ph-NH2
(b) aniline, p-methylaniline, p-nitroaniline
(c) aniline, pyrrole, pyridine, piperidine
(d) pyrrole, imidazole, 3-nitropyrrole
Predict the products from the reactions of the following amines with sodium nitrite in dilute.
The following partial IR spectra correspond to a primary amine, a secondary amine, and an alcohol. Give the functional group for each spectrum.
Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

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