Chemistry

Chapter 13 * The N + 1 Rule If a signal is split by N equivalent protons, it is split into N + 1 peaks. Chapter 13 Chapter 13 * Equivalent protons do not split each other. Protons bonded to the same carbon will split each other if they are nonequivalent. Protons on adjacent carbons normally will split each other. Protons separated by four or more bonds will not split each other. Spin-spin Splitting Distance Chapter 13 Chapter 13 * Long-Range Coupling When the hydrogen atoms are four bonds or more apart, spin-?spin splitting is not normally observed. When it actually does occur it is called ?long-range coupling.? Chapter 13 * Splitting for Ethyl Groups

Chapter 12 ?2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Infrared Spectroscopy and Mass Spectrometry Chapter 12 * Introduction Spectroscopy is a technique used to determine the structure of a compound. Most techniques are nondestructive (it destroys little or no sample). Absorption spectroscopy measures the amount of light absorbed by the sample as a function of wavelength. Chapter 12 Chapter 12 * Types of Spectroscopy Infrared (IR) spectroscopy measures the bond vibration frequencies in a molecule and is used to determine the functional group. Mass spectrometry (MS) fragments the molecule and measures their mass. MS can give the molecular weight of the compound and functional groups.

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 *