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Chapter 19: Q6P (page 988)

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

Short Answer

Expert verified

(a)

Basicity (pKb) of NaOH is 0.2

Basicity (pKb) of NH3 is 4.74

Basicity (pKb) of CH3NH2 is 3.38

Basicity (pKb) of Ph-NH2 is 9.38

Order of increasing basicity = Ph-NH2 < NH3 <CH3NH2 < NaOH

(b)

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of p-methylaniline is 9.21

Basicity (pKb) of p-nitroaniline is 12.99

Order of increasing basicity = p-nitroaniline< aniline < p-nitroaniline

(c)

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of pyridine is 8.77

Basicity (pKb) of piperidine is 4

Order of increasing basicity = pyrrole < aniline < pyridine < piperidine

(d)

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of imidazole is 7.0

3-nitropyrrole is formed by adding nitric acid to pyrrole i.e. nitration of pyrrole group.

Therefore it is less basic than pyrrole.

Order of increasing basicity = 3-nitopyrrole< pyrrole < imidazole

Step by step solution

01

Concept

pKb is the negative base -10 loh of the base dissociation constant (Kb) of the solution, which is used to determine the strength of base. Lower pkb value indicates a stronger base.

02

(a) NaOH, NH3, CH3NH2, Ph-NH2:

Basicity (pKb) of NaOH is 0.2

Basicity (pKb) of NH3 is 4.74

Basicity (pKb) of CH3NH2 is 3.38

Basicity (pKb) of Ph-NH2 is 9.38

Order of increasing basicity = Ph-NH2 < NH3 <CH3NH2 < NaOH

03

(b)  aniline, p-methylaniline, p-nitroaniline

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of p-methylaniline is 9.21

Basicity (pKb) of p-nitroaniline is 12.99

Order of increasing basicity = p-nitroaniline< aniline < p-nitroaniline

04

(c) aniline, pyrrole, pyridine, piperidine

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of pyridine is 8.77

Basicity (pKb) of piperidine is 4

Order of increasing basicity = pyrrole < aniline < pyridine < piperidine

05

(d) pyrrole, imidazole, 3-nitropyrrole

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of imidazole is 7.0

3-nitropyrrole is formed by adding nitric acid to pyrrole i.e. nitration of pyrrole group.

Therefore it is less basic than pyrrole.

Order of increasing basicity = 3-nitopyrrole< pyrrole < imidazole

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Most popular questions from this chapter

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(a) Explain this order:

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide to benzylamine

(b) 1-bromo-2-phenylethane to 3-phenylpropan-1-amine

(c) pentanoic acid to pentan-1-amine

(d) pentanoic acid to hexan-1-amine

(e) (R)-2-bromobutane to (S)-butan-2-amine

(f) (R)-2-bromobutane to (S)-2-methylbutan-1-amine

(g) hexan-2-one to 1-amino-2-methylhexan-2-ol

Propose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at 3-position.

Give the products expected from the following reactions:

(a) acetyl chloride + ethylamine

(b) benzoyl chloride +dimethylamine

(c) hexanoyl chloride + piperidine

The following partial IR spectra correspond to a primary amine, a secondary amine, and an alcohol. Give the functional group for each spectrum.
See all solutions

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