1 / 14

Acid Halides from Carboxylic Acids

Acid Halides from Carboxylic Acids. Synthesis of Acid Halides. SOCl 2 = thionyl chloride PCl 5 can also be used. Problems. Give the major product for the following reaction:

nieve
Download Presentation

Acid Halides from Carboxylic Acids

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Acid Halides from Carboxylic Acids

  2. Synthesis of Acid Halides • SOCl2 = thionyl chloride • PCl5 can also be used

  3. Problems • Give the major product for the following reaction: • Draw the products you would get from reacting the following molecule with PCl5. What product would you obtain from reacting it with PBr3?

  4. Anhydrides from Carboxylic acids • Anhydride = “without water” 20.9 Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides

  5. Problem • The second reaction on the previous page happens through a nucleophilic acyl substitution reaction. Draw the mechanism. • What product might you get upon heating of succinic acid?

  6. Reduction of Carboxylic Acids • The powerful reducing agent LiAlH4 is required • NaBH4 does not reduce carboxylic acids • The overall sequence for reduction is summarized as: 20.10 Reduction of Carboxylic Acids to Primary Alcohols

  7. Problems • Draw the reactant that forms the following product upon reduction with lithium aluminum hydride: • How might you prepare 2-phenylehtanol from benzyl bromide? More than one step is necessary.

  8. Decarboxylation of Carboxylic Acids • Decarboxylation: The loss of CO2 from RCO2H • Most ordinary carboxylic acids do not participate, but the following types do: 1. b-keto acids 2. Malonic acid derivatives (diacids) 3. Carbonic acid derivatives 20.11 Decarboxylation of Carboxylic Acids

  9. Decarboxylation from b-keto acids 20.11 Decarboxylation of Carboxylic Acids

  10. Decarboxylation from Malonic Acid Derivatives • This reaction also does not occur in base

  11. Decarboxylation of Carboxylic Acids • Decarboxylation from carbonic acid derivatives

  12. Problems • Give the products for the following reactions:

  13. Draw the mechanism for the decarboxylation reaction below:

More Related