Download Alcohols and Thiols - Lecture Slides | CHEM 30B and more Study notes Organic Chemistry in PDF only on Docsity! CH3 CH3CH2CH CH2 CH2 C CH3 CH2 C(CH3)2 BH3 THF Hg(OAc)2 H2O OH H CH3 AcOHg H BR2 H3C H NaBH4 HD_30BWinter2003Page 1 of 3 Chem30B_Winter_2003 Prof. Miguel A. Garcia-Garibay (MGG) TA: Hung Dang, dang@chem.ucla.edu Discussion Sections: Fridays: 9-10am (Geol 6704), 12-1pm (Geol 4645) Office Hour: Friday 10-11am (Young Hall 1379) and by appt. PS1 - Alcohols and Thiols (Chapter 9) 10January03 Review TOPICS: 1) Nomenclature - it is expected that you should be able to write the IUPAC names for a given structure and vice versa. To understand Organic Chemistry, we must be able to communicate our ideas and that entails being able to name compounds. However, for this class, you are only responsible to draw the structures when the name is provided. 2) Preparation of alcohols - Alcohols can be prepared from a variety of functional groups (e.g. alkenes, alkyl halides, ketones, esters, and aldehydes, among others) and they can be transformed into a wide range of compound types. a) Hydration of alkenes: H2O2 - OH trans-2-methylcyclohexanol (84%)syn non-Markovnikov Markovnikov 1-methylcyclohexanol (90%) Examples: Predict the product with stereochemistry where applicable. (a) 1. BH3 2. H2O2, NaOH (b) 1. Hg(OAc)2, H2O 2. NaBH4 (c) Reaction of cis-5-decene with OsO4, followed by NaHSO3 reduction. Be sure to indicate the stereochemistry of the product. CH3 NBS CCl4 H3O + H H CH2Br HO OH H OH HD_30BWinter2003Page 2 of 3 PS1 - Alcohols and Thiols (Chapter 9) 10January03 b) Alcohols from Reduction of Carbonyl Compounds: - In inorganic chemistry, reduction is defined as the gain of electrons (GER), and oxidation is defined as the loss of electrons (LEO). "LEO" the lion says "GER" Lose Electrons Oxidation (LEO) Gain Electrons Reduction (GER) However, in organic chemistry, deciding whether an atom loses or gains electrons during a reaction is difficult. For our purposes, an ORGANIC REDUCTION is a reaction that either increases the hydrogen content or decrease the oxygen, nitrogen, or halogen content of a molecule. Conversely, an ORGANIC OXIDATION is a reaction that either decreases the hydrogen content or increases the oxygen, nitrogen, or halogen content of a molecule. Example: - Catalytic hydrogenation of an alkene is clearly a reduction, since two hydrogens are added to the material. - Hydroxylation of an alkene with OsO4, however, is an oxidation because oxygen is added. - NBS allylic bromination of an alkene is an oxidation since a hydrogen is replaced by a halogen. - Hydration of an alkene is neither an oxidation nor a reduction, since both hydrogen and oxygen are added to the alkene at the same time. H2/Pd Ethanol 1. OsO4 2. NaHSO3
