Organic Chemistry

160 CHAPTER 4 Reactions of Alkenes How can we explain the regioselectivity of the preceding addition reaction? The electrophile ...

PROBLEM 18 Why are and unable to form covalent bonds? PROBLEM 19 What will be the product of the addition of I–Cl to 1-butene? ...

162 CHAPTER 4 Reactions of Alkenes Mechanistic Tutorial: Oxymercuration–reduction Synthetic Tutorial: Oxymercuration–reduction R ...

PROBLEM 22 How could the following compounds be synthesized from 3-methyl-1-butene? a. b. 4.9 Addition of Borane: Hydroboration– ...

164 CHAPTER 4 Reactions of Alkenes and borane is a Lewis acid. So the reagent actually used as the source of for the first step ...

Section 4.9 Addition of Borane: Hydroboration–Oxidation 165 carbon for the same reason: to form the more stable carbocation or c ...

166 CHAPTER 4 Reactions of Alkenes Mechanistic Tutorial: Hydroboration–oxidation Synthetic Tutorial: Hydroboration–oxidation The ...

PROBLEM-SOLVING STRATEGY A carbeneis an unusual carbon-containing species. It has a carbon with a lone pair of electrons and an ...

168 CHAPTER 4 Reactions of Alkenes hydrogens—isfollowed, however, because is the electrophile when HBr adds to an alkene in the ...

Section 4.10 Addition of Radicals • The Relative Stabilities of Radicals 169 When HBr reacts with an alkene in the absence of a ...

Initiation Steps.The first step is an initiation stepbecause it creates radicals. The second step is also an initiation step be ...

Section 4.11 Addition of Hydrogen • The Relative Stabilities of Alkenes 171 For the radical addition of HCl, the first propagati ...

172 CHAPTER 4 Reactions of Alkenes The details of the mechanism of catalytic hydrogenation are not completely under- stood. We k ...

bonded to its carbons, and the least stable of the three alkenes has only one alkyl substituent (an isopropyl group) bonded to i ...

When the large substituents are on the same side of the molecule, their electron clouds can interfere with each other, causing s ...

Section 4.12 Reactions and Synthesis 175 You will learn how alkenes are synthesized when you study compounds that undergo elimin ...

176 CHAPTER 4 Reactions of Alkenes Summary Alkenesundergo electrophilic addition reactions. Each re- action starts with the addi ...

Key Terms 177 c.Addition of halogen ( is the electrophile; Section 4.7) d.Acid-catalyzed addition of water and alcohols ( is the ...

178 CHAPTER 4 Reactions of Alkenes Problems Give the major product of each of the following reactions: Identify the electrophil ...

Problems 179 Draw curved arrows to show the flow of electrons responsible for the conversion of reactants into products. Give t ...