Organic Chemistry

140 CHAPTER 3 Alkenes• Thermodynamics and Kinetics CALCULATING KINETIC PARAMETERS In order to calculate and for a reac- tion, ra ...

A cyclic bromonium ion W e have seen that an alkene such as 2-butene undergoes an electrophilic addition reactionwith HBr (Secti ...

142 CHAPTER 4 Reactions of Alkenes This reactivity makes alkenes an important class of organic compounds because they can be use ...

Section 4.2 Carbocation Stability 143 The greater the number of alkyl substituents bonded to the positively charged carbon, the ...

144 CHAPTER 4 Reactions of Alkenes C H H H hyperconjugation δC δ+ + H H + H C H H CH 3 CH 2 + ethyl cation +CH 3 methyl cation F ...

Section 4.3 The Structure of the Transition State 145 George Simms Hammondwas born in Maine in 1921. He received a B.S. from Bat ...

146 CHAPTER 4 Reactions of Alkenes closely resemble the structure of the reactant than that of the product. In an endergonic rea ...

Section 4.4 Regioselectivity of Electrophilic Addition Reactions 147 The carbon that does notbecome attached to the proton is th ...

148 CHAPTER 4 Reactions of Alkenes The two different products in each of these reactions are called constitutional iso- mers. Co ...

We can say that adds preferentially to C-1 because C-1 is bonded to two hydro- gens, whereas C-2 is bonded to only one hydrogen. ...

150 CHAPTER 4 Reactions of Alkenes Mechanistic Tutorial: Addition of HBr to an alkene Because all the alkyl halide formed from 3 ...

Section 4.5 Addition of Water and Addition of Alcohols 151 Mechanistic Tutorial: Addition of water to an alkene PROBLEM 6 The a ...

152 CHAPTER 4 Reactions of Alkenes *At a pH of 4, for example, the concentration of is whereas the concentration of water in a d ...

Section 4.5 Addition of Water and Addition of Alcohols 153 a. How many transition states are there? b. How many intermediates ar ...

154 CHAPTER 4 Reactions of Alkenes Synthetic Tutorial: Addition of alcohol to an alkene Frank (Rocky) Clifford Whitmore (1887–19 ...

Section 4.6 Rearrangement of Carbocations 155 F. C. Whitmore was the first to suggest that the unexpected product results from a ...

156 CHAPTER 4 Reactions of Alkenes Carbocation rearrangements also can occur by ring expansion, another type of 1,2-shift. In th ...

Section 4.7 Addition of Halogens 157 d. This carbocation will not rearrange because it is a secondary carbocation and a carbo- c ...

158 CHAPTER 4 Reactions of Alkenes 3-D Molecule: Cyclic bromonium ion of cis-2-butene Mechanistic Tutorial: Addition of halogens ...

Section 4.7 Addition of Halogens 159 dissolves both reactants, but does not participate in the reaction. The foregoing reac- tio ...