Chapter 15: Carboxylic Acid Derivatives

Chapter 15: Carboxylic Acid Derivatives Chapter 15: Carboxylic Acid Derivatives - Start

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Chapter 15: Carboxylic Acid Derivatives




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Presentations text content in Chapter 15: Carboxylic Acid Derivatives

Slide1

Chapter 15: Carboxylic Acid Derivatives

Nucleophilic Acyl Substitution

Slide2

2

Carboxylic Acids and

Their Derivatives

Carboxylic Acid Derivatives:

Acid Halides

Acid Anhydrides

Slide3

Slide4

Types of anhydrides

:

Slide5

Cyclic esters

Slide6

Types of amides

Slide7

Cyclic amides

Slide8

Nomenclature Acid Halides

Acyl

groups named by replacing –ic

acid ending and adding –yl When the –COCl group is bonded to a ring: change the suffix –carboxylic acid

to –carbonyl chloride.

Slide9

Practice

Slide10

Slide11

Nomenclature Anhydrides

Symmetrical anhydrides are named by changing the acid ending of the carboxylic acid to the word

anhydride.

Mixed anhydrides, which are derived from two different carboxylic acids, are named by alphabetizing the names for both acids and replacing the word acid with the word anhydride.

Slide12

practice

12

Slide13

Slide14

Nomenclature Ester

The alkyl group (R’ ) on oxygen is named first. Followed by the

acyl portion and substituting –ic

acid ending of the parent carboxylic acid to the suffix –ate.

Slide15

PRACTICE

Slide16

Slide17

Nomenclature Amides

All 1

°

amides are named by replacing the -ic acid, -oic acid, or -ylic

acid ending with the suffix amide.

Slide18

Name the alkyl group (or groups) bonded to the N atom of the amide. Use the prefix “

N-

” preceding the name of each alkyl group to show that it is bonded to a nitrogen atom. This becomes the first part of the name.

For 3° amides, use the prefix di- if the two alkyl groups on N are the same. If the two alkyl groups are different, alphabetize their names. One “

N-” is needed for each alkyl group, even if both R groups are identical.

Name the acyl

group by replacing the –

ic

acid

,

-

oic

acid

, or

ylic

acid

ending by the suffix amide.

Slide19

Practice

Slide20

Slide21

Introduction to Nucleophilic Acyl Substitution

Nucleophilic

acyl substitutions is the characteristic reaction of carboxylic acid derivatives.This reaction occurs with both negatively charged nucleophiles and neutral nucleophiles

.

Slide22

Other

nucleophiles

that can participate in this reaction include:

Nucleophile: An atom or a group of atoms that donates a pair of

electron to another atom or group of atoms to form a new covalent bond. (Electron Rich)

Nucleophilic acyl substitution: A reaction in which a nucleophile bonded to a

Carbonyl carbon is replaced by another nucleophile.

Slide23

To draw any

nucleophilic

acyl product:

[1] Find the sp2 hybridized carbon with the leaving group.[2] Identify the nucleophile

.[3] Substitute the nucleophile for the leaving group. With a neutral nucleophile, the proton must be lost to obtain a neutral substitution product.

Slide24

Based on this order of reactivity, more reactive compounds can be converted into less reactive ones. The reverse is not usually true.

Amides

Carboxylic acids

Esters

Anhydrides

Acid Halides

Slide25

Acid chlorides react with oxygen nucleophiles to form anhydrides, carboxylic acids and esters.

Slide26

Acid chlorides also react with ammonia ,

1

° and 2° amines to form 1°, 2° and 3° amides respectively.

Two equivalents (the same chemical environment) of NH3 or amine are used.One equivalent acts as the nucleophile to replace

Cl, while the other reacts as a base with the HCl by-product to form an ammonium salt.

Slide27

As an example, reaction of an acid chloride with

diethylamine

forms the 30 amide N,

N-diethyl-m-toluamide, popularly known as DEET

.DEET is the active ingredient in the most widely used insect repellents.

Slide28

Reactions of Anhydrides

Nucleophilic

attack occurs at one carbonyl group, while the second carbonyl becomes part of the leaving group.

Slide29

Reactions of Esters

Esters are hydrolyzed with water in the presence of either acid or base to form carboxylic acids or

carboxylate anions respectively.

Basic hydrolysis of an ester is also called

saponification.

Slide30

Esters react with NH3

and amines to form 1°, 2°, or 3° amides.

Slide31

Reactions of Amides

Amides are the least reactive of the carboxylic acid derivatives.

Amides are hydrolyzed in acid or base to form carboxylic acids or

carboxylate anions.

Slide32

In acid, the amine by-product is

protonated

as an ammonium ion, whereas in base, a neutral amine forms.

Slide33


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