Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH...

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Carboxylic Acids

Transcript of Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH...

Page 1: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Carboxylic Acids

Page 2: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Introduction

The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon.

Carboxyl group is usually written -COOH .

Aliphatic acids have an alkyl group bonded to -COOH.

Aromatic acids have an aryl group.

Fatty acids are long-chain aliphatic acids.>=

Page 3: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Common Names

Many aliphatic acids have historical names.

Positions of substituents on the chain are labeled with Greek letters.

CH3CH2CHC

Cl

OH

O

-chlorobutyric acid

CH3CH2CH2CHCH2COOH

Ph

-phenylcaproic acid

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Page 4: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

IUPAC Names

Remove -e from alkane (or alkene) name, add -oic acid.

The carbon of the carboxyl group is #1.

CH3CH2CHC

Cl

OH

O

2-chlorobutanoic acid

PhC

HC

H

COOH

trans-3-phenyl-2-propenoic acid (cinnamic acid)

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Page 5: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Naming Cyclic Acids

Cycloalkanes bonded to -COOH are named as cycloalkanecarboxylic acids.

Aromatic acids are named as benzoic acids.

COOH

CH(CH3)2

2-isopropylcyclopentanecarboxylic acid

COOH

OH

o-hydroxybenzoic acid(salicylic acid)

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Page 6: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Dicarboxylic Acids

Aliphatic diacids are usually called by their common names (to be memorized).

For IUPAC name, number the chain from the end closest to a substituent.

Two carboxyl groups on a benzene ring indicate a phthalic acid.

HOOCCH2CHCH2CH2COOH

Br

3-bromohexanedioic acid -bromoadipic acid =>

Page 7: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Structure of Carboxyl

Carbon is sp2 hybridized.

Bond angles are close to 120.

O-H eclipsed with C=O, to get overlap of orbital with orbital of lone pair on oxygen.

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Page 8: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Boiling Points

Higher boiling points than similar alcohols, due to dimer formation.

Acetic acid, b.p. 118C =>

Page 9: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Melting Points

Aliphatic acids with more than 8 carbons are solids at room temperature.Double bonds (especially cis) lower the melting point. Note these 18-C acids:

Stearic acid (saturated): 72COleic acid (one cis double bond): 16CLinoleic acid (two cis double bonds): -5C>=

Page 10: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Solubility

Water solubility decreases with the length of the carbon chain.

Up to 4 carbons, acid is miscible in water.

More soluble in alcohol.

Also soluble in relatively nonpolar solvents like chloroform because it dissolves as a dimer. >=

Page 11: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Acidity

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Page 12: Carboxylic Acids. Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Carboxyl group is usually.

Resonance Stabilization

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Carboxylic acids

Carboxylic acids

Carboxylic Acids, Esters & Amides. Carboxylic Acids Carboxyl group = functional group -COOH Easily produced through the oxidation of an aldehyde Carboxylic.

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1 Chapter 15: Carboxylic Acids and Esters. 2 CARBOXYLIC ACIDS The functional group of carboxylic acids is the carboxyl group. Many carboxylic acids have.

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Organic Acids - Carboxylic Acids

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Chapter 13 Carboxylic acids 13.1 Nomenclature 13.2 Acidity of carboxylic acids Factors affecting the acidity of carboxylic acids Dicarboxylic acids 13.3.

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Chemistry 2100 Chapter 19. Carboxyl Derivatives In this chapter, we study three classes of compounds derived from carboxylic acids; anhydrides, esters,

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Carboxylic acids: R – COOH COOH = “carboxyl group” · PDF fileStructure, nomenclature and occurrence of acid derivatives: Esters: Typically originate from a carboxylic acid and

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CONTENTS Structure of carboxylic acids Nomenclature Physical properties of carboxylic acids Preparation of carboxylic acids Chemical properties of carboxylic.

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Carboxylic Acids. Nomenclature of Carboxylic Acids Esters.

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CHAPTER 19: Carboxylic Acids and Derivatives I 19...CHAPTER 19: Carboxylic Acids and Derivatives I 19.1 Carboxylic Acids 19.2 Reactions of Carboxylic Acids 19.3 Esters Learning outcomes:

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Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education.

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1 Carboxylic Acids, Esters, Amines and Amides Carboxylic Acids Properties of Carboxylic Acids Esters Esterification and Hydrolysis.

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General structure Carboxyl group...SCH 206 Dr. Solomon Derese Carboxylic acids General structure R O O H Carboxyl group Acidic R= alkyl, alkenyl, alkynyl or aryl 17 The word carboxy

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Chapter 19: Carboxyl Derivatives In this chapter, we study three classes of compounds derived from carboxylic acids; anhydrides, esters, and amides. –

Chapter 19: Carboxyl Derivatives In this chapter, we study three classes of compounds derived from carboxylic acids; anhydrides, esters, and amides. –

Carboxylic Acids. A carboxylic acid contains a carboxyl group, which is a carbonyl group attach to a hydroxyl group. carbonyl group O CH 3 — C—OH hydroxyl.

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Structure and Naming of Carboxylic Acids Carboxylic acids contain a carbonyl attached to a hydroxyl group; this is called a carboxyl group Parent name.

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Carboxylic Acids The functional group of a carboxylic acid is a carboxyl group. Structure of Carboxylic Acids The general formula of an aliphatic carboxylic.

Carboxylic Acids The functional group of a carboxylic acid is a carboxyl group. Structure of Carboxylic Acids The general formula of an aliphatic carboxylic.