chapter10 - Chapter 10 Problems 10.1-38, 42-43, 45-46. 10....

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Chapter 10 Problems 10.1-38, 42-43, 45-46. 10. Synthetic Uses of Substitution and Elimination Reactions This chapter discusses how one can use substitution and elimination reactions to synthesize organic molecules. 10.1 Substitution Reactions Reactions that proceed via the S N 2 mechanism are preferred. Changes in stereochemistry and rearrangements are observed for S N 1 reactions. Substrates with leaving groups attached to 1 o and methyl carbons are excellent S N 2 reactants, 2 o carbons are ok as long as the nucleophile is weakly basic. S N 1 reactions must be used for substrates with leaving groups attached to 3 o carbons. 10.2 Preparation of Alcohols Alcohols can be prepared for alkyl halides using either HO - or H 2 O as a nucleophile. Hydroxide ion reacts with 1 o alkyl halides or 2 o halides that are either benzylic, allylic, or adjacent to a carbonyl. Examples Hydroxide is not typically used for 3 o alkyl halides due to the competing E2 reaction. Water is used as the nucleophile and reactions follow an S N 1 mechanism. Example The reaction of 2 o alkyl halides with hydroxide gives poor yield of substitution products to the competing E2 reaction. So one can use a less basic hydroxide alternative – acetate (CH 3 CO 2 - ). Acetate gives better yield of substitution product and then subsequent reaction with hydroxide yields the desired alcohol. Example
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10.3 Preparation of Ethers Ethers can be formed by using alcohols or alkoxide as the nucleophile. When alkoxide is
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This note was uploaded on 04/17/2009 for the course CHM 227 taught by Professor Rosen during the Fall '08 term at Rhode Island.

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chapter10 - Chapter 10 Problems 10.1-38, 42-43, 45-46. 10....

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