Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 23.5, Problem CQ
Interpretation Introduction

Interpretation:

Factor that accounts for the pyramidalization geometry of NH2 group present in aniline has to be identified from the given options.

Concept introduction:

Hybridization is the mixing of valence atomic orbitals to get equivalent hybridized orbitals that having similar characteristics and energy.

  • sp3  hybrid orbitals is produced by hybridization of single s-orbital and three p-orbital.
  • sp2  hybrid orbitals is produced by hybridization between one s-orbital and two p-orbitals.
  • sp  hybrid orbitals is produced by hybridization of single s-orbital and single p-orbital.

Resonance is an electron displacement effect for stabilizing a molecule through delocalization of bonding electrons in the pi orbital.

Delocalized electrons stabilize a compound. The extra stability gains from having delocalized electrons are called resonance stabilization or resonance energy.

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What accounts for the geometry (pyramidalization) of the NH2 group in aniline? 1. Resonance between the NH2 group and the benzene ring. 2. The electronic withdrawing nature of the sp2 carbons in the phenyl group. 3. Participation of the nitrogen lone pair to make the system aromatic. 4. Both 1 and 3.
Comment on the functional groups of rilpivirine. What functional groups does it contain and circle them. How do the aromatic rings interact? What are the intermolecular forces and how do they interact with the target.
Biphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.

Chapter 23 Solutions

Organic Chemistry

Ch. 23.5 - Prob. FQCh. 23.5 - Prob. GQCh. 23.5 - Select the stronger acid from each pair of...Ch. 23.6 - Prob. 23.7PCh. 23.6 - Prob. 23.8PCh. 23.6 - Prob. 23.9PCh. 23.7 - Prob. 23.10PCh. 23.8 - Prob. 23.11PCh. 23.8 - Prob. 23.12PCh. 23.8 - Prob. 23.13PCh. 23.9 - Prob. 23.14PCh. 23.10 - In Example 23.15, you considered the product of...Ch. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Prob. 23.19PCh. 23 - Prob. 23.20PCh. 23 - Prob. 23.21PCh. 23 - Prob. 23.22PCh. 23 - Account for the formation of the base peaks in...Ch. 23 - Prob. 23.24PCh. 23 - Select the stronger base from each pair of...Ch. 23 - The pKa, of the conjugate acid of morpholine is...Ch. 23 - Which of the two nitrogens in pyridoxamine (a form...Ch. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - Prob. 23.30PCh. 23 - Prob. 23.31PCh. 23 - Suppose you have a mixture of these three...Ch. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - Prob. 23.35PCh. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - (S)-Glutamic acid is one of the 20 amino acid...Ch. 23 - Prob. 23.39PCh. 23 - Propose a structural formula for the compound...Ch. 23 - Prob. 23.41PCh. 23 - The pyrolysis of acetic esters to give an alkene...Ch. 23 - Propose steps for the following conversions using...Ch. 23 - Show how to bring about each step in this...Ch. 23 - Show how to bring about each step in the following...Ch. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - Methylparaben is used as a preservative in foods,...Ch. 23 - Prob. 23.51PCh. 23 - Prob. 23.52PCh. 23 - Propose a synthesis for the systemic agricultural...Ch. 23 - Prob. 23.54PCh. 23 - Several diamines are building blocks for the...Ch. 23 - Prob. 23.56PCh. 23 - Prob. 23.57PCh. 23 - Prob. 23.58PCh. 23 - Prob. 23.59PCh. 23 - Following is a retrosynthesis for the coronary...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - Given this retrosynthetic analysis, propose a...Ch. 23 - Prob. 23.64PCh. 23 - Following is a series of anorexics (appetite...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Show how the synthetic scheme developed in Problem...Ch. 23 - Prob. 23.69PCh. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72P
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