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 Introduction 2 Carboxylic acids are organic compounds containing the carboxyl group (-COOH), wherein the hydroxyl group (-OH) is directly attached

CARBOXYLIC ACIDS...Carboxylic Acids Introduction 2 Carboxylic acids are organic compounds containing the carboxyl group (-COOH), wherein the hydroxyl group (-OH) is directly attached

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

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

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 AND DERIVATIVES. Naming of Carboxylic acids.

CARBOXYLIC ACIDS AND DERIVATIVES. Naming of Carboxylic acids.

10.4 Carboxylic Acids and Esters Carboxylic Acids These are compounds with a carboxyl group, which consists of a carbonyl group and a hydroxyl group.

10.4 Carboxylic Acids and Esters Carboxylic Acids These are compounds with a carboxyl group, which consists of a carbonyl group and a hydroxyl group.

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

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

Chemistry 2100 Lecture 6. Carboxyl Derivatives In this chapter, we study three classes of compounds derived from carboxylic acids; anhydrides, esters,

Chemistry 2100 Lecture 6. Carboxyl Derivatives In this chapter, we study three classes of compounds derived from carboxylic acids; anhydrides, esters,

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

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

Chapter 4 Lipids - KSUfac.ksu.edu.sa/sites/default/files/4-bch302_lipids_i_0.pdf · Fatty acids are aliphatic carboxylic acids Fatty acids are long hydrocarbon chain preceded by carboxyl

Chapter 4 Lipids - KSUfac.ksu.edu.sa/sites/default/files/4-bch302_lipids_i_0.pdf · Fatty acids are aliphatic carboxylic acids Fatty acids are long hydrocarbon chain preceded by carboxyl

STRUCTURE OF CARBOXYLIC ACIDS contain the carboxyl functional group COOH the bonds are in a planar arrangement.

STRUCTURE OF CARBOXYLIC ACIDS contain the carboxyl functional group COOH the bonds are in a planar arrangement.

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

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

Carboxylic Acids Carboxyl group: -CO 2 H, -COOH Pure carboxylic acids form hydrogen bonded dimers very high boiling points (higher than alcohols) H-bond.

Carboxylic Acids Carboxyl group: -CO 2 H, -COOH Pure carboxylic acids form hydrogen bonded dimers very high boiling points (higher than alcohols) H-bond.

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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Chapter 16 Carboxylic Acids and Esters - Cerritos Collegecms.cerritos.edu/uploads/ahoang/Powerpoint/Unit4 - Carboxylic Acids... · A carboxylic acid Contains a carboxyl ... Esterification.

Chapter 16 Carboxylic Acids and Esters - Cerritos Collegecms.cerritos.edu/uploads/ahoang/Powerpoint/Unit4 - Carboxylic Acids... · A carboxylic acid Contains a carboxyl ... Esterification.

Chapter 10 Carboxylic Acids 1Chapter 10. 2 Introduction Carbonyl (-C=O) and hydroxyl (-OH) on the same carbon is carboxyl group. Carboxyl group is usually.

Chapter 10 Carboxylic Acids 1Chapter 10. 2 Introduction Carbonyl (-C=O) and hydroxyl (-OH) on the same carbon is carboxyl group. Carboxyl group is usually.

Chapter 12 Carboxylic Acids. Chapter 202 Introduction Carbonyl (-C=O) and hydroxyl (-OH) on the same carbon is carboxyl group. Carboxyl group is usually.

Chapter 12 Carboxylic Acids. Chapter 202 Introduction Carbonyl (-C=O) and hydroxyl (-OH) on the same carbon is carboxyl group. Carboxyl group is usually.

CARBOXYLIC ACIDS Since the carboxyl group is polar, carboxylic acids contain dipole-dipole forces, London forces and are able to hydrogen bond. Therefore.

CARBOXYLIC ACIDS Since the carboxyl group is polar, carboxylic acids contain dipole-dipole forces, London forces and are able to hydrogen bond. Therefore.

CARBOXYLIC ACIDS By Dale & Cameron. GENERAL STRUCTURE A carboxylic acid is an organic acid that contains a carboxyl group. A carboxyl group is simply.

CARBOXYLIC ACIDS By Dale & Cameron. GENERAL STRUCTURE A carboxylic acid is an organic acid that contains a carboxyl group. A carboxyl group is simply.

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

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

Carboxylic acids

Carboxylic acids