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Transcript
Chem 130 Fall 2004 Exam 3 Study Guide Chapter 8.1-8.4 – Alcohols 1. Nomenclature of Alcohols 2. Properties Hydrogen Bonding: boiling point 3. Reactions of Alcohols Conversion into alkyl halides (with HCl, HBr, SOCl2) Dehydration to form alkene (with H2SO4, concentrated, ∆) Oxidation: Primary alcohol to aldehydes (with PCC) Primary alcohol to carboxylic acids (with CrO3 or K2Cr2O7) Secondary alcohol to ketones (with PCC or CrO3 or K2Cr2O7) Tertiary alcohol: no reaction Conversion into ethers, ROR (with Na metal, then RCl) Chapter 9.1-9.4, 9.6-9.8 – Benzene and its Derivatives 1. Structure of the benzene ring 2. Electrophilic Aromatic Substitution: Benzene (nucleophile) + electrophile (E+) Bromination (Br+): Br2/FeBr3 Chlorination (Cl+): Cl2/FeCl3 Nitration (NO2+): HNO3/H2SO4 Sulfonation (+SO3H): SO3/ H2SO4 Alkylation (R+): RCl/AlCl3 Acylation (RC+=O): RCOCl/AlCl3 3. Substituent Effects (orientation effects for monosubstituted products) Ortho/Para activating substituents: -NH2, -OH, -OCH3, -R Ortho/Para deactivating substituents: -Cl, -Br Meta deactivating substituents: -NO2, -CN, -SO3H, -COCH3, -COOH, -CO2CH3, -CH=O (aldehyde) 4. Mechanisms of Electrophilic Aromatic Substitution Chapter 13.1-13.8, 13.10-13.11 – Aldehydes and Ketones 1. Nomenclature 2. Reactions Oxidation of aldehydes to carboxylic acids (with CrO3 or K2Cr2O7 or AgNO3 in NH4OH) Reduction of aldehydes to primary alcohol (with NaBH4) Reduction of ketones to secondary alcohol (with NaBH4) Grignard reaction and mechanism: synthesis of alcohols (formation of new carbon-carbon bond)