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Not all tertiary haloalkanes undergo SN1 reactions readily. For example, the bicyclic

Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote ISBN: 9781133952848 483

Solution for problem 9.27 Chapter 9

Organic Chemistry | 7th Edition

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Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Organic Chemistry | 7th Edition

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Problem 9.27

Not all tertiary haloalkanes undergo SN1 reactions readily. For example, the bicyclic com-pound shown below is very unreactive under SN1 conditions. What feature of this mol-ecule is responsible for such lack of reactivity? You will find it helpful to examine a modelof this compound.

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Hybridization of Atomic Orbitals Linus Pauling­ 1935 Hybridization (combined) Atomic Orbitals­ different atomic orbitals can combine to give new hybrid orbitals These hybrid orbitals reflect the geometry of the molecule The problem comes from not knowing which molecules hybridize and which ones don’t Predicting Hybridization of Atomic Orbitals Difficult to predict Rules 1. Determine the geometry of the regions of high electron density 2. Assign the set of hybridized orbitals that corresponds to the geometry Sp ­ linear, 180° 2 Sp ­ trigonal, 120° 3 Sp ­ tetrahedral, 109.5° 3 Sp d ­ trigonal bipyramidal, 120°, 90° 3 2 Sp d ­ octahedral, 90° Only three possible hybridization modes for Carbon­ Sp, Sp , Sp2 3 Geometry of Hybridization of Orbitals 180° Sp Linear (180°) Sp 120° Sp 2 Sp Trigonal planar (120°) flat 3 Sp 109.5° Tetrahedral (109.5°) This is the most common type of Carbon found 90° 3 Sp d Trigonal bipyramidal 120° (120°, 90°) Sp d 2 90° Octahedral (90°) 90° *Black outline = flat region Red outline = vertical region Hybridization of Carbon Structure of carbon and methane Structure of ground carbon: C: 1s , 2s , 2Px, 2Py

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Chapter 9, Problem 9.27 is Solved
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Textbook: Organic Chemistry
Edition: 7
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
ISBN: 9781133952848

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 7. Since the solution to 9.27 from 9 chapter was answered, more than 275 students have viewed the full step-by-step answer. The answer to “Not all tertiary haloalkanes undergo SN1 reactions readily. For example, the bicyclic com-pound shown below is very unreactive under SN1 conditions. What feature of this mol-ecule is responsible for such lack of reactivity? You will find it helpful to examine a modelof this compound.” is broken down into a number of easy to follow steps, and 44 words. This full solution covers the following key subjects: . This expansive textbook survival guide covers 24 chapters, and 1131 solutions. The full step-by-step solution to problem: 9.27 from chapter: 9 was answered by , our top Chemistry solution expert on 03/16/18, 05:02PM. Organic Chemistry was written by and is associated to the ISBN: 9781133952848.

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Not all tertiary haloalkanes undergo SN1 reactions readily. For example, the bicyclic