Alcohols, Phenols, and Thiols Nanoplasmonic Research Group Organic Chemistry Chapter 7 Part II.

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Presentation transcript:

Alcohols, Phenols, and Thiols Nanoplasmonic Research Group Organic Chemistry Chapter 7 Part II

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 (S N 1 or S N 2) Nucleophilicity of halide ion is not strong enough for S N 2 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 S N 1 ? Why not S N 2 ? Because of the geometry of the ring!! Due to extremely unstable phenyl cation

Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids Primary Alcohol Secondary alcohol AldehydeCarboxylic acid Ketone Please refer to a few reactions on page 222