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Transcript
Organic Chemistry Chapter 7 Part II Alcohols, Phenols, and Thiols Nanoplasmonic Research Group Chemical Reactions with Alcohols • Dehydration to Alkenes • Conversion to Alkyl Halides • Oxidation Dehydration of Alcohols to Alkenes (E1 or E2) Protonation of the hydroxyl group Formation of carbocation intermediate Beta elimination The Reaction of Alcohols with Hydrogen Halides - Alkyl Halides Formation - Substitution Reaction (SN1 or SN2) Nucleophilicity of halide ion is not strong enough for SN2 Please refer to page 219 Another way to alkyl halides!!! - Treatment with thionyl chloride - Convert the hydroxyl group to a good leaving group!!!! Since hydrogen chloride and sulfur dioxide are gases and evolve from the product, we don’t need to separate the desired alkyl halide from the mixture!!!! Please take a look at equation 7.33 on page 221 Why doesn’t phenols undergo the substitution reactions ? Why not SN1 ? Due to extremely unstable phenyl cation Why not SN2 ? Because of the geometry of the ring!! Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids Primary Alcohol Aldehyde Secondary alcohol Carboxylic acid Ketone Please refer to a few reactions on page 222
