Detailed Chapter Notes - Carboxylic Acids & Acids Derivatives, Class 12, Chemistry Class 12 Notes | EduRev

Class 12 : Detailed Chapter Notes - Carboxylic Acids & Acids Derivatives, Class 12, Chemistry Class 12 Notes | EduRev

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Nomenclature of Aldehydes and Ketones - Aldehydes, Ketones and Carboxylic Acids, Class 12, Chemistry

Introduction : 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Table – 1 : IUPAC Nomenclature of Acid derivatives :-

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Dicarboxylic Acids

If the subsituent is a second carboxyl gropu, we have a dicarboxylic acid. For example :

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important                    Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important                 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Oxalic acid                             Malonic acid -1, 3-         Succinic acid -1, 4-

Ethanedioic acid                      dioicacid                           dioic acid

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important                       Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important                    Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Glutaric acid                            Adipic acid                                 Pimelic acid

Pentane-1, 5-dioicacid          Hexane-1, 6-dioicacid        Heptane-1, 7- dioci acid

 

HOOCCH2COOH    HOOCCH2CH2COOH    HOOCCH2CH2CH2CH2COOH

Malonic acid                   Succinic acid              Adipic acid

Propanedioic acid        Butanedioic acid                Hexanedioic acid

 

========================================================

Physical Properties of Aldehydes and Ketones - Aldehydes, Ketones and Carboxylic Acids, Class 11, Chemistry

Physical properties of acids and acid derivatives :

 

Boiling point :

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important                    Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important            Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important                                                                                                                                                       Acetic acid,                             1-propanol                                          Propionaldehyde

bp 1180C                                   bp910C                                                 bp490C

The high boiling points of carboxylic acids is the result of formation of a stable hydrogen-bonded dimer.

 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

Hydrogen bonded acid dimer

Solubility :

Carboxylic acids form hydrogen bonds with water and the lower molecular –weight carboxylic acids (upto 4 carbon atoms) are miscible with water.

Acid derivatives (esters, acid chlorides, anhydride, nitriles and amides) are soluble organic solvents such as alcohols, ethers, chlorinated alkanes and aromatic hydrocarbons.

 

Methods of preparation of carboxylic acids

1. Synthese of carboxylic acids by the carboxylation of grignard reagentsAldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

2- Synthesis of Carboxylic acids by the hydrolysis of nitriles Mechanism :

 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

  Nitrile                                                                  carboxylic acid

 

Chemical Reactions

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Reaction of carbroxylic acid with aqueous sodium carbonatge solution produces brisk efferuescnce. However most phenols do not produce effervescence. Therefore, the reaction may be used to distinguish between carboxylic acids and phenols.

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

If we follow the forward in this mechanism, we have the mechanism for the acid catalysed esterification fo an acid. If however, we follow the reverse reactions, we have the meachanism for the acid catalysed hydrolysis of an ester. Acid catalysed ester hydrolysis.

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Formation of amides :

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Formation of acid anhydride :

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

4-     Decarboxylation reactions:

1   Soda-lime decarboxylation :

 

General reaction:

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

2   Decarboxylation of  b- keto carboxylic acids :

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

 



Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important- keto acid

 

3   Kolbe electrolysisAldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

4   Hunsdiecker Reaction (Brome-decarboxylation):Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

5.       HVZ Reaction (Halogenation of aliphatic acids and Substituted acids)

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

                              Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Carboxylic Acid Derivatives

Closely related to the carboxylic acids and to each other are a number of chemical families known as functional derivatives of carboxylic acids : acid chloride, anhydrides, amide, and esters, These derivatives are compounds in which the  -OH of a carboxyl group has been replaced by–Cl, -OOCR, -NR2 or –OR
Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

Acid chloride                       Anhydride                    Amide                                   Ester


Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

They all contain the acyl group ,

 (A)    Acid halides

Methods of preparations of Acyl halides

(i) RCOOH PCl5  → RCOCl POCl3  HCl

(ii) 3RCOOH PCl3 → 3RCOCl H3PO3

(iii) RCOOH SOClAldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important RCOCl SO2  HCl

Ex.       3CH3 COONa PCl3 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 3CH3 COCl Na3PO3

                                                                     Acetyl chloride

Ex.       2C6H5COONa POCl3 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 2C6H5COCl NaCl NaPO3

             Sod. benzoate                                 Benzoyl chloride

 

 

Chemical Reactions

 

Reaction with carboxylic acids

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Acyl                    Carboxylic                               Acid                    Hydrogen

chloride                   acid                               anhydride               chloride

 

2 Reaction with alcohols

Acyl chlorides react with alcohols to form esters. The reaction is typically carried out in the presence of pyridine.Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

 Acyl              Alcohol                          Ester             Hydrogen

choride                                                                      chloride

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

        

Hydrolysis

 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

                       

4 Reaction of acid halide with organometallic

(a) with Grignard reagent

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important           

(b) Reaction with Gilmann reagent

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

 

5 Reduction of acid halided

(a)  Reduction LiAlH4

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important           

 

(b) Reduction with H2/Pd/BaSO Rosenmund reduction

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

(B)     Acid amides

            Methods of preparation of acids amides

1. By reaction of esters with ammonia and amines

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Ammonia is more nucleophilic than water, making it possible to carry out this reaction using aqueous ammonia.

 

Ex.Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

2. From acid halides

RCOCl 2NH3 → RCONH2  NH4Cl

 

3. From anhydride

(RCO)2O 2NH3 → RCONH2  RCOO NH4

4. From esters

RCOOR NH3 → RCONH2  R’OH

 5. From ammonium salt of carboxylic acid

RCOONH4 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important RCONH2  H2O

CH3 COONH4 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3CONH2

 

6. From cyanides

R – C º N H2Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important R – CONH2

CH3C = N H2Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3 - CONH2

 

7.

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Chemical Reactions

(1)       Hoffmann rearrangement

General reaction

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

(2) Hydrolysis of amides

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

In acid, however, the amine is protonated, giving an ammonium ion, R2’ Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

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Summary of reaction of amide:

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(C) Esters

Methods of Preparation

(i) CH3 COOH C2H5OH Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3COOC2 H5  H2O

                        Acetic acid

 C6H5COOH CH3OH Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important C6H5 COOCH3  H2O

 

(ii) CH3 COCl C2H5OH Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3COOC2H5  HCl

Alcohols react with acyl chlorides by nucleophilic acyl substitution to yield esters. These reactions are typically perormed in the presence of a weak base such as pyridine.

 Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Summary of reaction of esters :

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

(D) Acid anhydrides

Methods of Preparation of acid anhydrides

            1- From carboxylic acids

Ex.      CH3COOH HOOCCH3  Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3CO.O.COCH3  H2O

            Acetic acid                                                       Acetic anhydride

Ex.

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Ex.     

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

 

2. From acid and acid halide

Ex.      CH3COOH CH3COCl Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3 CO.O.COCH3  HCl

Ex.      CH3COCl CH3COONa Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important CH3CO.O.COCH3  NaCl

 

Chemical Reactions

1   Reaction with aromatic compounds (Friedel crafts acylation)

 

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

Reaction with alcohols

Ex.

   Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

 

3  Reaction with ammonia and amines

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

4 Hydrolysis

 Acid anhydrides react with to yield two carboxylic. Cycylic anhydides yield dicarboxylic acids.

          Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

            Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

 

5-     Heating Effects: 

 a Heating effect on monocarboxylic acid

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

 

Heating effect on dicarboxylic acid

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

Heating effect on Hydroxy acids

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Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

 

1- Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, ImportantHydroxy acid

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, ImportantAldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important       

 

2. Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, ImportantHyroxy acid

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important    

 

3- Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, ImportantHydroxy acid

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important

Since 4 or 8 membered rings are less stable the refore b-Hydroxy acids on heating produce a, b unsaturated carboxylic acid.

 

4- aa -Hyroxy acid

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

 Û Heating effect on esters

Aldehydes, Ketones, Carboxylic Acids, CBSE, Class XII, IIT JEE, Syllabus, Preparation, AIPMT, NCERT, Important 

This reaction follows syn elimination & hoffman product is formes.

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