Alkene

Chapter 15 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy Chaper 15 * Conjugated Systems Conjugated double bonds are separated by one single bond. Isolated double bonds are separated by two or more single bonds. Conjugated double bonds are more stable than isolated ones. Chaper 15 Chaper 15 * Heat of Hydrogenation of Conjugated Bonds For conjugated double bonds, the heat of hydrogenation is less than the sum for the individual double bonds. The more stable the compound, the less heat released during hydrogenation, Conjugated double bonds have extra stability. Chaper 15 Chaper 15 * Relative Stabilities twice 1-pentene more substituted Chaper 15 Chaper 15 * Structure of 1,3-Butadiene

Chapter 8 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Reactions of Alkenes Chapter 8 * Bonding in Alkenes Electrons in pi bond are loosely held. The double bond acts as a nucleophile attacking electrophilic species. Carbocations are intermediates in the reactions. These reactions are called electrophilic additions. Chapter 8 Chapter 8 * Electrophilic Addition Step 1: Pi electrons attack the electrophile. Step 2: Nucleophile attacks the carbocation. Chapter 8 Chapter 8 * Types of Additions Chapter 8 Chapter 8 * Addition of HX to Alkenes Step 1 is the protonation of the double bond. The protonation step forms the most stable carbocation possible. In step 2, the nucleophile attacks the carbocation, forming an alkyl halide.

Chapter 8 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Reactions of Alkenes Chapter 8 * Bonding in Alkenes Electrons in pi bond are loosely held. The double bond acts as a nucleophile attacking electrophilic species. Carbocations are intermediates in the reactions. These reactions are called electrophilic additions. Chapter 8 Chapter 8 * Electrophilic Addition Step 1: Pi electrons attack the electrophile. Step 2: Nucleophile attacks the carbocation. Chapter 8 Chapter 8 * Types of Additions Chapter 8 Chapter 8 * Addition of HX to Alkenes Step 1 is the protonation of the double bond. The protonation step forms the most stable carbocation possible. In step 2, the nucleophile attacks the carbocation, forming an alkyl halide.

Chapter 11 Reactions of Alcohols ?2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Chapter 11 * Types of Alcohol Reactions Dehydration to alkene Oxidation to aldehyde, ketone Substitution to form alkyl halide Reduction to alkane Esterification Tosylation Williamson synthesis of ether Chapter 11 Chapter 11 * Summary Table Chapter 11 Chapter 11 * Oxidation States Easy for inorganic salts: CrO42- reduced to Cr2O3. KMnO4 reduced to MnO2. Oxidation: Gain of O, O2, or X2; loss of H2. Reduction: Gain of H2 (or H-); loss of O or O2; and loss of X2. The gain or loss of H+, H2O, HX, etc. is neither an oxidation nor a reduction. Chapter 11 Chapter 11 * Oxidation States of Carbons Chapter 11 Chapter 11 *

Chapter 10 ?2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Structure and Synthesis of Alcohols Chapter 10 * Structure of Water and Methanol Oxygen is sp3 hybridized and tetrahedral. The H?O?H angle in water is 104.5?. The C?O?H angle in methyl alcohol is 108.9?. Chapter 10 Chapter 10 * Classification of Alcohols Primary: carbon with ?OH is bonded to one other carbon. Secondary: carbon with ?OH is bonded to two other carbons. Tertiary: carbon with ?OH is bonded to three other carbons. Aromatic (phenol): ?OH is bonded to a benzene ring. Chapter 10 Chapter 10 * Examples of Classifications C H 3 C C H 3 C H 3 O H * C H 3 C H O H C H 2 C H 3 * C H 3 C H C H 3 C H 2 O H * Primary alcohol Secondary alcohol Tertiary alcohol Chapter 10 Chapter 10 *