Chapter 11-Alcohol Reactions

Chapter 11-Alcohol Reactions - CH3CH2CH2 Br H C O H H H...

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CH 3 CH 2 CH 2 C H H Br O H H Chapter 11 Reactions of Alcohols
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CH 3 CH 2 CH 2 C H H Br O H H Types of Alcohol Reactions =>
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CH 3 CH 2 CH 2 C H H Br O H H 1º, 2º, 3º Carbons =>
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CH 3 CH 2 CH 2 C H H Br O H H
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CH 3 CH 2 CH 2 C H H Br O H H Oxidation of 1° Alcohols 1° alcohol to aldehyde to carboxylic acid Difficult to stop at aldehyde Use pyridinium chlorochromate (PCC) to limit the oxidation. PCC can also be used to oxidize 2° alcohols to ketones. CH 3 CH 2 CH 2 CH 2 OH N H CrO 3 Cl CH 3 CH 2 CH 2 CH O
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CH 3 CH 2 CH 2 C H H Br O H H Oxidation of 2° Alcohols 2° alcohol becomes a ketone • Reagent is chromic acid: Na 2 Cr 2 O 7 /H 2 SO 4 *3 ° alcohols do not oxidize CH 3 CHCH 2 CH 3 OH Na 2 Cr 2 O 7 / H 2 SO 4 CH 3 CCH 2 CH 3 O =>
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CH 3 CH 2 CH 2 C H H Br O H H Other Oxidation Reagents • Cr 2 O 3 in pyridine • KMnO 4 in H 2 O (strong oxidizer) CuO, 300°C (industrial dehydrogenation) Biological Oxidation- Catalyzed by ADH, alcohol dehydrogenase Ethanol oxidizes to acetaldehyde, then acetic acid, a normal metabolite.
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Chapter 11-Alcohol Reactions - CH3CH2CH2 Br H C O H H H...

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