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Chapter 25: Q35P (page 1029)

In each pair of compounds, select the stronger base, and explain your choice.
(a) HOCH2NH2and CH3NH2 (b) PhNH2 and PhCH2CH2NH2

(c)(d)

Short Answer

Expert verified

(a)

CH3NH2 is more basic than OHCH2NH2

(b)

PhCH2CH2NH2is more basic than PhNH2.
(c)


(d)

Step by step solution

01

CH3NH2 is more basic than OHCH2NH2

CH3NH2 is more basic than OHCH2NH2because in the second one the OH group have electron withdrawing effect to takes electrons toward it and making less electrons nitrogen. So the second compound is less basic.

02

PhCH2CH2NH2 is more basic than PhNH2

PhCH2CH2NH2is more basic than PhNH2because in second structure there is a resonance contribution making the nitrogen less electrons available. So the first structurte[H2] is more basic thean the second.

03

Steric hinderence.

The cyclic compound is more basic because of lower steric hindrance.

04

Presence of extra methyl group in first structure.

In both structures the resonance makes less available of electrons. But in first structure the presence of methyl group makes the nitrogen lone pairs of electron more available. So first is more basic than the second.

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Most popular questions from this chapter

Question. Using any necessary reagents, show how you can accomplish the following multistep synthesis.

Question. Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.



  1. Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion,. Be careful to draw all the resonance structures of this intermediate.
  2. Explain why pyrrole reacts more readily than benzene, and also why substitution occurs primarily at the 2-position rather than 3-position.

Question. The following spectra for A and B correspond to two structural isomers. The NMR singlet at1.16in spectrum A disappears when the sample is shaken with . The singlet at 0.6 ppm in the spectrum B disappears on shaking with . Propose structures for these isomers, and show how your structures correspond to the spectra. Show what cleavage is responsible for the base peak at 44 in the mass spectrum of A and the prominent peak at 58 in the mass spectrum of B.

Question. Using any necessary reagents, show how you would accomplish the following syntheses.

Question. Synthesize from benzene. (Hint: Some of these require diazonium ions.)

  1. 4-methylaniline
  2. 3-ethylphenol
  3. 2-ethyl-5-hydroxybenzoic acid
  4. 4-ethoxyaniline
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