CHM231 Study Guide for Exam 3: Topics in Organic Chemistry (Fall, 2010) - Prof. Oliver Gra, Study notes of Organic Chemistry

Download CHM231 Study Guide for Exam 3: Topics in Organic Chemistry (Fall, 2010) - Prof. Oliver Gra and more Study notes Organic Chemistry in PDF only on Docsity! CHM231 study guide for test 3 (Fall, 2010) This study guide is intended to help you prepare for the third exam on Monday, November 15th. In general, anything covered in the lecture up to the exam could be part of the exam. However, this guide tries to help you focus on the main requirements. Chapter 7: Haloalkanes 7.9 Mechanisms of -eliminationseliminations -eliminations mechanisms of E1 and E2 reactions -eliminations equation for reaction rates -eliminations energy diagrams -eliminations preferred reaction products (most substituted alkene) -eliminations conditions when E1 mechanism is favored and when E2 mechanism is favored 7.10 Substitution vs. Elimination -eliminations conditions that favor substitution reactions -eliminations conditions that favor elimination reactions Chapter 8: Alcohols, Ethers, and Thiols 8.2 Alcohols -eliminations IUPAC nomenclature -eliminations be able to distinguish primary, secondary and tertiary alcohols -eliminations physical properties: boiling points and solubilities in water hydrogen bonds vs. dipole-eliminationsdipole interactions vs. London forces => how do they affect boiling points and water solubility 8.3 Reactions of Alcohols -eliminations acidity and basicity -eliminations reaction with Na and K -eliminations SN1, SN2 reactions i) preferred products ii) mechanisms; acid catalysis because OH-eliminations is a poor leaving group! iii) electronic and steric factors that determine the mechanism, e.g. 1°, 2°, and 3° carbocations iv) reaction with SOCl2 -eliminations E1 and E2: acid catalyzed dehydration of alcohols i) mechanisms ii) preferred products (most substituted alkene) -eliminations oxidation of primary and secondary alcohols i) with chromic acid, or sodium/potassium dichromate ii) with PCC (what distinguishes the oxidation of primary alcohols with PCC from oxidation with chromate or dichromate?) -eliminations tertiary alcohols are not oxidized by either PCC or chromic acid 8.4 Ethers -eliminations IUPAC nomenclature of aliphatic ethers -eliminations physical properties: boiling points and solubilities in water What distinguishes the intermolecular interactions in ethers from those in alcohols? -eliminations ether synthesis from alcohols and haloalkanes (nucleophilic substitution) 8.5 Epoxides