Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 1, Problem 1.29P
Interpretation Introduction

(a)

Interpretation:

For the given ion, all the resonance structures are to be drawn.

Concept introduction:

If a molecule or ion has one of the following features, another resonance structure will exist:

  1. A lone pair on an atom adjacent to a multiple bond
  2. An atom with incomplete octet next to a multiple bond or next to an atom with one or more lone pairs.
  3. Alternating double/triple and single bonds.

The movement of an electron pair is shown with a curved arrow, starting at the pair and ending on the atom or region where it moves. The movement must be from a relatively electron rich atom or region to a relatively electron deficient atom or region.

Interpretation Introduction

(b)

Interpretation:

For the given ion, all the resonance structures are to be drawn.

Concept introduction:

If a molecule or ion has one of the following features, another resonance structure will exist:

  1. A lone pair on an atom adjacent to a multiple bond
  2. An atom with incomplete octet next to a multiple bond or next to an atom with one or more lone pairs.
  3. Alternating double/triple and single bonds.

The movement of an electron pair is shown with a curved arrow starting at the pair and ending on the atom or region where it moves. The movement must be from a relatively electron rich atom or region to a relatively electron deficient atom or region.

Interpretation Introduction

(c)

Interpretation:

For the given ion, all the resonance structures are to be drawn.

Concept introduction:

If a molecule or ion has one of the following features, another resonance structure will exist:

  1. A lone pair on an atom adjacent to a multiple bond
  2. An atom with incomplete octet next to a multiple bond or next to an atom with one or more lone pairs.
  3. Alternating double/triple and single bonds.

The movement of an electron pair is shown with a curved arrow starting at the pair and ending on the atom or region where it moves. The movement must be from a relatively electron rich atom or region to a relatively electron deficient atom or region.

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(a) Draw all resonance contributors of the following ion. In drawing each additional resonance structure, use curved arrows to indicate which pairs of electrons are being shifted. (b) Draw the resonance hybrid. (c) Which c–C bond is the longest?
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Chapter 1 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Prob. 1.14PCh. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Prob. 1.27PCh. 1 - Prob. 1.28PCh. 1 - Prob. 1.29PCh. 1 - Prob. 1.30PCh. 1 - Prob. 1.31PCh. 1 - Prob. 1.32PCh. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Prob. 1.35PCh. 1 - Prob. 1.36PCh. 1 - Prob. 1.37PCh. 1 - Prob. 1.38PCh. 1 - Prob. 1.39PCh. 1 - Prob. 1.40PCh. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - Prob. 1.56PCh. 1 - Prob. 1.57PCh. 1 - Prob. 1.58PCh. 1 - Prob. 1.59PCh. 1 - Prob. 1.60PCh. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Prob. 1.68PCh. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Prob. 1.75PCh. 1 - Prob. 1.76PCh. 1 - Prob. 1.77PCh. 1 - Prob. 1.78PCh. 1 - Prob. 1.79PCh. 1 - Prob. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.1YTCh. 1 - Prob. 1.2YTCh. 1 - Prob. 1.3YTCh. 1 - Prob. 1.4YTCh. 1 - Prob. 1.5YTCh. 1 - Prob. 1.6YTCh. 1 - Prob. 1.7YTCh. 1 - Prob. 1.8YTCh. 1 - Prob. 1.9YTCh. 1 - Prob. 1.10YTCh. 1 - Prob. 1.11YTCh. 1 - Prob. 1.12YTCh. 1 - Prob. 1.13YTCh. 1 - Prob. 1.14YTCh. 1 - Prob. 1.15YTCh. 1 - Prob. 1.16YTCh. 1 - Prob. 1.17YT
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