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 AQ
Interpretation Introduction

Interpretation:

Reason for why angle found in p-nitroaniline means that the amine group is planar and in the same plane as the benzene ring has to be determined 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.

Geometry of different types of molecule with respect to the hybridizations are mentioned are mentioned below,

TypeofmoleculeHybridaizationAtomicorbitalsusedforhybridaizationGeometryAX2sp1s+1pLinearAX3,AX2Bsp21s+2pTrigonalplanarAX4,AX3B,AX2B2sp31s+3pTetrahedralAX5,AX4B,AX3B2,AX2B3sp3d1s+3p+1dTrigonalbipyramidalAX6,AX5B,AX4B2sp3d21s+3p+2dOctahedralACentralatomXAtomsbondedtoABNonbondingelectronpairsonA

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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Students have asked these similar questions
Q.The angle found in p-nitroaniline means that the amine group is planar and in the same plane as the benzene ring. Why is this the case? 1. The nitro group withdraws the lone pair electrons from the amine, primarily via induction, making the N atom sp2 hybridized and hence trigonal planar. 2. The nitro group withdraws the lone pair electrons from the amine, primarily via resonance, making the N atom sp2 hybridized and hence trigonal planar. 3. The lone pair of the N atom of the NH2 must be in a p orbital to make the system aromatic. 4. The nitrogen of an amine is usually planar, and aniline and methylamine are exceptions.
Draw the Lewis diagram of Serotonin. Mark the electron geometry and molecular geometry of 6 interior atoms. Draw the Serotonin structure using skeletal notation here. Mark all sigma bonds, all pi bonds, and the hybridization of all interior atoms.
For the following descriptions of molecules, draw the Lewis structure (showing all atoms, lone pairs, formal charges) of the molecule and show all bond angles (assuming ideal VSEPR angles). An organic compound with the molecular formula H3CNO2. C is sp2 hybridized, N is sp3 hybridized, one O is sp² hybridized, while the second O is sp3 hybridized. An organic compound with the molecular formula H2CNO*. Both C and O are sp hybridized while N is sp³ hybridized.

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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