Organic Chemistry

260 CHAPTER 6 Reactions of Alkynes • Introduction to Multistep Synthesis Addition of hydrogen (Section 6.8) Removal of a proton ...

Problems 261 Give the systematic name for each of the following structures: a. c. b. d. What reagents could be used to carry ...

262 CHAPTER 6 Reactions of Alkynes • Introduction to Multistep Synthesis Which of the following pairs are keto–enol tautomers? ...

benzene cyclohexane A s you continue your study of organic chemistry, you will notice that the concept of having delocalized ele ...

264 CHAPTER 7 Electron Delocalization and Resonance • More About Molecular Orbital Theory with delocalized electrons. You will a ...

Section 7.1 Delocalized Electrons: The Structure of Benzene 265 In 1865, the German chemist Friedrich Kekulé suggested a way of ...

266 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory KEKULÉ’S DREAM Friedrich August Kekulé ...

Section 7.3 Resonance Contributors and the Resonance Hybrid 267 a. b. c. d. 7.2 The Bonding in Benzene Benzene is a planar molec ...

268 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory resonance structure. The actual structu ...

Section 7.4 Drawing Resonance Contributors 269 3-D Molecule: Cyclooctatetraene 7.4 Drawing Resonance Contributors We have seen t ...

270 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory δ+ resonance contributors resonance hyb ...

Section 7.4 Drawing Resonance Contributors 271 Tutorial: Drawing resonance contributors O O O O O O O O O O δ+ resonance contrib ...

272 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory δ δ δ δ δ δ resonance contributors reso ...

PROBLEM 3 a. Predict the relative bond lengths of the three carbon–oxygen bonds in the carbonate ion b. What would you expect t ...

274 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory Structures Cand Dare predicted to be eq ...

Section 7.6 Resonance Energy 275 We can summarize the features that decrease the predicted stability of a contributing resonance ...

276 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory ∆H ̊ = −85.8 kcal/mol (−359 kJ/mol) ∆H ...

contributors,the greater is the resonance energy. For example, the resonance energy of a carboxylate ion with two relatively sta ...

Then compare the predicted stabilities of the set of resonance contributors for each carbocation. Each carbocation has two reson ...

A benzylic cation has five resonance contributors. Notice that the positive charge is shared by four carbons. Not all allylic an ...