有机化学Chapter8_LIJI_简版.pptVIP

Chapter 8 Chapter 8 * Chapter 8 * Chapter 8 * Let’s first talk about the kinds of reactions in general: * In general alkenes undergo addition reactions. They do so in a specific way that is related to their bonding: ? p bond - two loosely held electrons ? weaker than s bond ? good nucleophile there are two patterns - Less common both electrophilic and nucleophilic character avoids carbocation- but strained ring In each case the alkene’s p elctrons act as a Lewis base There are many reactions in this chapter but the same features keep reappearing!! Chapter 8 electrophile nucleophile carbocation intermediate Chapter 8 * Addition of acids, HX (actually we’ll see that X can also be a whole lotta’ other things!) 1. overall reaction a. ionic addition - the most common 2. mechanism There are actually two different ones- Chapter 8 * Chapter 8 * The first step in the reaction mechanism leads directly to a orientational preference Markovinkov’s rule: the hydrogen atom from HX goes to the less substituted end of the alkene. Why? Chapter 8 * Chapter 8 * B. Addition of H-OH - hydration of alkenes 1. overall reaction Chapter 8 * 2. mechanism - exactly opposite to the dehydration reaction to form alkenes Chapter 8 * 3. orientation - Markovinkov addition Chapter 8 * C. Addition of H-OSO3H (H2SO4) and hydration ? industrial application ? substitution of H2O - prob. SN1 ? Markovnikov orientation Chapter 8 * H. Addition of halogens 1. overall reaction 2. mechanism ?note relationship to the addition of carbenes cyclic bromonium ion Chapter 8 * H. Ozonolysis 1. overall reaction Chapter 8 * 2. mechanism Chapter 8