1 / 8

Carboxylic acid

alcohols. p799 (special). p798 (special)**. Carboxylic acid. Amide. p814. p795-6 acid and base. p794-5. p803 - need to work out. p802. p810 acid and base. Acid chloride. p795 – need to work out. p807 – need to work out. Ester. Acid anhydride.

leiko
Download Presentation

Carboxylic acid

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. alcohols p799 (special) p798 (special)** Carboxylic acid Amide p814 p795-6 acid and base p794-5 p803 - need to work out p802 p810 acid and base Acid chloride p795 – need to work out p807 – need to work out Ester Acid anhydride

  2. Chapter 21 – addition then R drops off - substitution 1. R- is halide – Acid Halides 2. R – is RCOO – Acid anhydride (same as 1) 3. R- is RO - ester 4. R- is RNH – amide (same as 3) 5. R- is OH – carboxylic acid Increasingly unreactive

  3. Chapter 21 – addition then R drops off - substitution 1. R- is halide – Acid Halides Nu is H2O - Hydrolysis of Acid halides (21.4 p.802 – top) Nu is ROH – Esterification/alcoholysis (p 802 – bottom) Nu is RCOOH – Acid anhydride (p 802 middle) Nu is amine - amide/amminolysis (p 803)

  4. Chapter 21 – addition then R drops off - substitution 2. R- is carboxylate – Acid anhydride (mechanism exactly same as acid chloride) – carboxylate not so good leaving group so Slightly less reactive. Nu is H2O - Hydrolysis of Acid anhydride (p 806 bottom) Nu is ROH – Esterification/alcoholysis (p 807 – top) Nu is amine - amide/amminolysis (p 807 - middle) Classwork: 21.14

  5. Chapter 21 – addition then R drops off - substitution R- is alkoxide – Ester alkoxide not so good leaving group so must be catalysed by acid or base Slightly less reactive. Nu is H2O - Hydrolysis of ester base (Fig 21.7) / acid (Fig 21.8) Nu is ROH – trans esterification/alcoholysis Nu is amine - amide/amminolysis Classwork: 21.43

  6. Chapter 21 – addition then R drops off - substitution R- is amine – amide amine not so good leaving group so must be catalysed by acid or base Slightly less reactive – exactly same mechanism as ester Nu is H2O - Hydrolysis of ester / acid (p 814)

  7. Chapter 21 – addition then R drops off - substitution R- is OH – Carboxylic acid OH very bad leaving group so must be converted into a good leaving group by reacting with some reagent Nu is ROH - Esterification / acid catalysed (Fig 21.4) Nu is “amine” – induction with DCC (Fig 21.5) Nu is ‘halide” - SOCl2 (p 795 top) Classwork: 21.36(h); 21.41

  8. Chapter 21 – addition then R drops off - substitution Other types of nucleophiles (not covered in this module) “hydride ion” - reduction with LiAlH or NaBH4 Grignard reagent and other organometallics Homework: 21.44, 21.48, 21.52

More Related