Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions. McMurray Text Chapter 21

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1 Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution eactions McMurray Text Chapter 21

2 Carboxylic Acid Derivatives X Acid alide Ester ' Acid Anhydride ' N 2 Amide (1 )

3 Nomenclature Acid alides (Acyl alides) Change ic acid in the parent carboxylic acid to yl followed by the halide. 3 C Cl acetyl chloride (from acetic acid) Cl Cl hexanedioyl chloride (from hexanedioic acid) 3 C 2 CC C 3 Cl 2-methylbutanoyl chloride (from 2-methylbutanoic acid)

4 Nomenclature Symmetrical Acid Anhydrides Change acid in the parent carboxylic acid to anhydride. acetic anhydride (from 2 acetic acids) butanoic anhydride (from 2 butanoic acids)

5 Nomenclature Unsymmetrical Acid Anhydrides Name the two acids alphabetically and change acid to anhydride. acetic benzoic anhydride ethanoic methanoic anhydride

6 Nomenclature Esters Name group bonded to, followed by replacing ic acid in the parent acid with ate. ethyl acetate Et Et diethyl propanedioate methyl butanoate isopentyl acetate

7 Nomenclature Amides 1 amides: Change oic acid (IUPAC) or -ic acid (common) in the parent acid to amide. N 2 acetamide 2 and 3 amides: First identify the substituent groups (preceded by N- )and then the parent amide. N N N-Methylacetamide N,N-Dimethylformamide

8 Nucleophilic Acyl Substitution Lv + Nu Lv Nu Nu + Lv tetrahedral intermediate

9 eactivity of Acid Derivatives: Steric Effects C < < C C < C eactivity toward nucleophilic substitution Most indered Least indered

10 eactivity of Acid Derivatives: Electronic Effects N 2 Amide < < < ' ' Ester Acid Anhydride X Acid alide eactivity toward nucleophilic substitution Carbonyl carbon least electrophilic Carbonyl carbon most electrophilic

11 Nucleophilic Acyl Substitution xns 1 Alcoholysis 1 eduction - - Y Grignard eagent 1 MgX 1 1 MgX N 2 Aminolysis N 3 ydrolysis 2

12 Preparation of Acyl alides SCl 2 Cl PBr 3 Br Note: Acid fluorides are extremely reactive and require different preparation methods.

13

14 Preparation of Anhydrides eat Carboxylic acid Carboxylic acid Anhydride C C eat + 2 Cyclic Anhydride Succinic acid Succinic anhydride Na - Na + 1 Cl 1 Mixed Anhydride

15 Fischer Esterification Preparation of Esters Note: If one uses labeled alcohol, the label is retained in the product.

16 Preparation of Amides No simple method for the preparation of amides from carboxylic acids! Amides from acids discussed in 26.10

17 Interconversion of Derivatives All acid derivatives can be converted to carboxylic acids. A derivative can be converted to a less reactive derivative. A derivative cannot be converted to a more reactive derivative. Anhydrides can be converted to esters and amides, but not into acid halides.

18 Interconversion

19 Lecture 2 (with review)

20 eactivity of Acid Derivatives: Electronic Effects N 2 Amide < < < ' ' Ester Acid Anhydride X Acid alide eactivity toward nucleophilic substitution Carbonyl carbon least electrophilic Carbonyl carbon most electrophilic

21 Nomenclature Acid chloride: -yl chloride Anhydride: anhydride Ester: -ate Amide: amide 3 C Cl acetyl chloride (from acetic acid) isopentyl acetate

22 Nucleophilic Acyl Substitution Lv + Nu Lv Nu Nu + Lv tetrahedral intermediate

23 Interconversion

24 Acid alide ydrolysis Cl Acid 2 Cl 2 A base such as pyridine, triethylamine, or Na is used to remove the Cl that is formed.

25 Acid alides into Anhydrides Acid chloride/carboxylate reaction useful for preparing either symmetrical or unsymmetrical anhydrides. Na - Na + 3C Cl C 3 Mixed Anhydride

26 Acid alide Alcoholysis Cl + + N N Cl + Ester

27 Acid alide Aminolysis C Cl 2 N 3 C N 2 + N 4 Cl Formation of a primary amide Benzoyl Chloride Benzamide C Cl 2 N C 3 C N C 3 + C 3 N 3 Cl Formation of a secondary amide C Cl 2 N C 3 C N C 3 + N Cl - Formation of a tertiary amide C 3

28 Cl N Cl N m-toluyl chloride N N 3 amide! Cl N,N-diethyl-m-toluamide (DEET)

29 Acid alide eduction C Cl 1 Ester 1. LA C Aldehyde LA C Primary alcohol C Cl 1 MgX Grignard eagent C Ketone 1 1 MgX 1 1 C Tertiary alcohol

30 Acid alides into Ketones Gilman reagent: 2 CuLi (lithium diorganocopper) C Cl (C 3 ) 2 CuLi C C 3 No overoxidation as opposed to Grignard reactions! Note: Carboxylic acids, esters, acid anhydrides, and amides do not react with Gilman reagents.

31 Acid Anhydride eactions Less reactive than acid chlorides, but react in a similar fashion ydrolysis eact with water to form carboxylic acids Alcoholysis eact with alcohols to form esters Aminolysis eact with amines to form amides eduction eact with LiAl4 to form 1 alcohols

32 Alcoholysis: Acid Anhydride Ester Aminolysis: Amide

33 Ester ydrolysis base-catalyzed hydrolysis C 2 C C 2 C C C (C 2 ) 16 C 3 (C 2 ) 16 C 3 (C 2 ) 16 C 3 (saponification) C 2 Na 2 C C(C 2 ) 16 C C 2 Na Triglyceride Glycerol Sodium Stearate Soap C 1 C 1 C C + 1

34 Ester ydrolysis acid-catalyzed hydrolysis (reverse Fischer Esterification) C 1 C 1 C 1 C 1 C + 1 C C Acid

35 Ester Aminolysis Esters react with ammonia and with 1 and 2 amines to form amides. Ph Et + N 3 Ph + Et N 2

36 Ester eduction C 1 Ester 1. LA C Aldehyde LA C Primary alcohol C Cl 1 MgX Grignard eagent C Ketone 1 1 MgX 1 1 C Tertiary alcohol

37 Amide ydrolysis C N C Acid

38 Amide eduction Amides into Amines using LiAl 4 Product of reduction is an amine, not an alcohol as with the other acid derivatives C N 2 1. LA C N 2 Primary amine C N 2 Al 3 C N 2 N C C N 2 Primary amine

39 Nucleophilic Substitution xns Summary Product Starting Material Acid Chloride Acid Anhydride Carboxylic Acid Ester Amide Acid Chloride - xn xn xn xn Acid Anhydride 0 - xn xn xn Carboxylic Acid xn xn - xn xn Ester 0 0 xn - xn Amide 0 0 xn 0-0 = No reaction

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