ch 20 - CHAPTER 20 Carboxylic Acid Derivatives The more...

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CHAPTER 20 Carboxylic Acid Derivatives
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The more resonance the shorter the C L bond The more resonance, the shorter the C-L bond.
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Alcohols convert alkanoyl chlorides into esters . A base is usually added to neutralize the HCl produced by the reaction. The basic or neutral conditions employed in this method avoid the equilibrium problem of acid- catalyzed ester formation. Amines convert alkanoyl chlorides into amides . Aqueous ammonia can be used for the synthesis of simple amines since it is a much stronger nucleophile than water. The HCl formed is neutralized by a base, which can be excess amine.
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Di-organo-cuprates convert alkanoyl chlorides into ketones . RLi or RMgX are unselective and may add more than once leading to alcohol formation. Alkanoyl chlorides are reduced to alcohols when NaBH 4 or LiAlH 4 are used directly are used directly. If LiAlH 4 is first reacted with three molecules of tert - butanol , which reduces the nucleophilicity of the remaining hydride ion, reduction stops at the aldehyde.
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Transesterification : Conversion of one ester into
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ch 20 - CHAPTER 20 Carboxylic Acid Derivatives The more...

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