CHM 234: Synthesis and Alcohol
CHM 234: Synthesis and Alcohol CHM 234
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This 9 page Class Notes was uploaded by Alvin Notetaker on Saturday January 30, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 35 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.
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Date Created: 01/30/16
Synthesis: I. Functional Group Transformations: __________________________________________________________________ Review: ● Elimination reaction is based on thebase used to determine whether the more or less substituted alkene is formed. ● Addition reaction is based on whether peroxide is used to formantiMarkovnikov or Markovnikov addition. ● Hydroxyl from must be made into a better leaving group like TsCl with pyridine . ● Regiochemical outcome can be manipulated by choice of reagents. __________________________________________________________________ II. Reactions that Change the Carbon Skeleton: A. Increasing Carbon Skeleton ● Alkylation of a terminal alkyne increases the carbon. B. Decreasing Carbon Skeleton ● Ozonolysis of Alkene ○ C=C is reactive toward oxidative cleavage ○ Ozone is in resonance Example: ● Ozonolysis of Alkynes ○ Oxidative cleavage with alkynes starts withozone and water to produce carboxylic acid . nternal Alkynes.) ○ When a terminal alkynes undergo oxidative cleavage, it produces carbon dioxide . Example: III. Retrosynthetic Analysis: Synthesis Backwards ○ Retrosynthetic Analysis is the process of mentally breaking down a molecule into the starting molecule. ○ Target Molecule is the molecule to be synthesized. ○ Retrosynthetic arrow indicate a reverse reaction. ○ Synthon are fragments resulting from a disconnection. ● Approaching synthesis problem: ○ Ask how the carbon chain has changed ○ Ask how the functional group has changed. 1) Regiosynthesis: Synthesis: 2) Regiosynthesis: Synthesis: Alcohol: 1. Structure and Properties of Alcohols ● Nomenclature a. Find the parent chain which should include the hydroxyl group. b. Find the substituents and name them. c. The hydroxyl group should have the lowest number. d. Put the name in alphabetical order e. the suffix ends with “ol” instead of “e”. ■ Replace “e” with “ol” Pentane Pentan1ol , 1pentanol ■ Longest chain Parent:Hexane Parent:Pentanol ■ OH have more precedence over the others like double bonds. (Bottom numbers are correct) ■ Name placement: just before the parent name or just before the ol suffix Pentan3ol , 3pentanol ■ R and S should be place before the name. (R)2chloro3phenylpropan1ol Phenyl ■ On cyclic alcohols, the OH group is one carbon 1 and it is omitted Cyclopentanol (R)3,3dimethylcyclopentanol ■ Common names isopropyl alcohol tertButyl alcohol Benzyl alcohol Benzyl ● Classification of Alcohols Type Primary alcohol Secondary alcohol Tertiary alcohol Structure ● When a OH group is on a benzene ring, it is called, phenol. Phenol 4chloro2nitrophenol ● Commercially Important Alcohols ○ Methanol ○ Ethanol ○ Denatured alcohol ethanol with small toxin compound (such as methanol) ○ Isopropanol industrial solvent, antiseptic and as a gasoline additive ● Physical properties of Alcohols Boiling point = −89°C Boiling point = 12°C Boiling point = 78°C ○ Since they can Hbond, they can attract water strongly ○ Alcohols with a small carbon chain are miscible in water (Right: Hydrophobic , Left: Hydrophilic) ○ The larger the chain, the less miscible 2. Acidity of Alcohols and Phenols ● Acidity of the Hydroxyl Functional group ● Reagents for Deprotonating an Alcohol ○ Deprotonation of an alcohol compound will produce an alkoxide ion ● Factors Affecting the Acidity ● ○ Resonance Cyclohexanol pka= 18 Phenol The resonancestabilized anion is called a phenolate or a phenoxide ion pka= 10 ○ Induction Ethanol pka= 16 Trichloroethanol pka= 12.2 ○ Solvation Effects ■ Less sterically hindered = more easily solvated ■ More sterically hindered = less easily solvated
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