Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 1, Problem 1.85P
Interpretation Introduction

(a)

Interpretation: The reason for difference in bond lengths of the bond [1] and bond [2] is to be stated.

Concept introduction: With an increase in the s character, bond strength increases and ultimately bond length decreases. This is because the electrons are held more tightly and closer to the nucleus by the hybrid orbitals.

Interpretation Introduction

(b)

Interpretation: The reason for equal bond length of bonds [3] and [4] and shorter bond length than bond [2] is to be stated.

Concept introduction: Resonance plays a significant role in stabililizing the molecule and it is responsible for properties exhibited by the molecule.

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Use the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?
3. (a) Draw a resonance structure for Molecule 1 in Box B, which satisfies the octet for all non- hydrogen atoms. Hint you may want to use curved arrows to move electrons over the skeleton of Molecule 3 to help you find the resonance structure. H H H H Molecule 1 H H 3. (b) Fill in the table below for Molecule 1 Box B: Resonance Structure of Molecule 1 VSEPR electron pair geometry around atom Molecular geometry Approximate bond or shape around atom angles around atom N atom CH3 C atom CH C atoms 3. (c) Given the information that resonating electrons are delocalized and so are not used to determine VSEPR geometry, how will the table you filled in for 3.(b) change?
Use the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?

Chapter 1 Solutions

Organic Chemistry

Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Draw a second resonance structure for each...Ch. 1 - Prob. 1.14PCh. 1 - Draw a second resonance structure for nitrous...Ch. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Simplify each condensed structure by using...Ch. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - Classify each bond in the following molecules as ...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Two radioactive isotopes of iodine used for the...Ch. 1 - Prob. 1.40PCh. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each N and O atom in the...Ch. 1 - Draw one valid Lewis structure for each compound....Ch. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 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 - Draw all reasonable resonance structures for each...Ch. 1 - Prob. 1.56PCh. 1 - Rank the resonance structures in each group in...Ch. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - Predict the geometry around each indicated atom....Ch. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Each of the following condensed or skeletal...Ch. 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 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Label the polar bonds in each molecule. Indicate...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.79PCh. 1 - The principles of this chapter can be applied to...Ch. 1 - a. What is the hybridization of each N atom in...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 1.85PCh. 1 - Prob. 1.86PCh. 1 - Prob. 1.87PCh. 1 - Prob. 1.88PCh. 1 - Prob. 1.89PCh. 1 - Prob. 1.90P
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