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ALDEHYDE, KETONEAND CARBOXYLIC ACID

rganic Compounds having C O group are called carbonyl compounds and

C O group is known as carbonyl or oxo group. It's general formula is Cn H2nO

(n = 1, 2, 3......) Carbonyl compounds are grouped into two categories.

In aldihydes,the carbonyl group is bonded to a carbon and hydrogen while in ketones,it is bonded to two carbon atoms.The carbonyl compounds in which carbonyl groupis bonded to oxygen are known as carboxylic acids, and their derivatives (e.g. esters,anhydrides) while in compounds where carbon is attached to nitrogen and to halogensare called amides and acyl halides respectively.

Aldehydes, ketones and carboxylic acids are play an important role in biochemicalprocesses, add fragrance and flavour to many food products and pharmaceuticals.

INTRODUCTION

In organic chemistry, we have learnt to derive from compoundscontaining only carbon and hydrogen i.e. from the hydrocarbons, allother types of combinations such as alcohol, aldehyde, ketones, acidsetc.

''OTTO WALLACH''

O

CHAPTER 12

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ALDIHYDE, KETONE & CARBOXYLIC ACID

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E ST TOO INS KEY PO

C OH,

O..

C X,

O..

C NH ,2

O..

C OR,

O..

In all the compounds given above, lone pair of electrons and double bond are conjugate.

C Z

O.. so resonance occurs. These compounds have C

O

group still they are not carbonyl compoundsbecause carbonyl group takes parts in resonance with the lone pair of electrons.

General Methods of Preparation :(A) For both Aldehydes and Ketones

By Oxidation of Alcohols :

Primary alcohols Aldehydes

Secondary alcohols Ketones

By K2Cr2O7 / H2SO4 :Oxidation of primary alcohols gives aldehyde and oxidation of secondary alcohols gives Ketones. Here,(K2Cr2O7 / H2SO4) is a strong oxidising agent.

2RCH OH RCHO (Aldehyde)

CH R

OH

R C R

O

R (Ketone)

Aldehydes are quite susceptible to further oxidation to acids -

RCH2OH R—CHO R—COOHThus oxidation of primary alcohols is made at the temperature much above the boiling point of aldehyde andthus aldehydes are vapourised out and prevented from being oxidised.Note : Aldehydes can be prepared from 1° alcohol, secondary alcohols can be oxidized to ketones, by oxidationwith pyridinium chlorochromate (PCC) in CH2Cl2 solvent, pyridinium dichromate (PDC) and with Jones reagent(CrO3+H2SO4) in acetone.

Oppenauer Oxidation :The oxidation of secondary alcohols to ketones by heating them with specific reagent : [(CH3)3CO]3Al(Aluminium-t-butoxide) in presence of acetone. Primary alcohols may also be oxidized to aldehydes if ketonesis replaced by a better hydrogen acceptor, e.g. p-benzoquinone. The equilibrium can be controlled by the amountof acetone, an excess of which favours the oxidation of the alcohol.

CHOHR

R + C O

CH3

CH3

C O +R

R CH OH

CH3

CH3

2O Alcohol Acetone Ketone Isopropyl alcohol

RCH2OH + O O R—CHO + HO— —OH

10 Alcohol Quinone Aldehyde QuinolNote : The reaction is the reverse of Meerwein-Ponndorf -verley reduction.

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CHEMISTRY FOR NEET & AIIMS

BENZALDEHYDE (C6H5CHO)

Oil of bitter almondsGeneral Method of Preparation :


ALDEHYDE, KETONE AND CARBOXYLIC ACID

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Ex. 1 Find out unknown in following reactions.

AlcoholDehydration

(B)(A)

Br2 (C)(i) alc. KOH(ii) NaNH2

(D)

Hg / H SO++2 4(E)

(CH –COO) Ca3 2

Reduction

Sol. Since E is obtained on dry distillation of calcium salt of acetic acid hence E will be . Thus otherunknowns are

A = B = CH3 – CH = CH2

C = D = CH3 – C C – H

Ex. 2 What will be structure of aromatic C8H8Cl2 (A), which on aqueous alkalihydrolysis gives product (B). (B) givespositive iodoform test.

Sol. Since (B) is showing iodoform test hence it will be methylketone only as it is obtained on aqueous alkali hydrolysisof (A) which will be non-terminal gem dihalides as –

KOH KOH

Now unknown 'R' can be known as :

= C8H8Cl2

R = C8H8Cl2 – C2H3Cl2 = C6H5 Hence 'A' is

Ex. 3 Write the products of the following reactions.

(A) (B)

(C) (D)

SOLVED EXAMPLE

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1. The end product in the following sequecne of reaction is

HC CH 1%HgSO

20%H SO

4

2 4

A CH MgX [O]3 B

(A) Acetic acid (B) Isopropyl alcohol (C) Acetone (D) Ethanol

2. In the following reaction, product P is R C Cl

OH

Pd — BaSO

2

4

P(A) RCH2OH (B) RCOOH (C) RCHO (D) RCH3

3. Acetophenone is prepared from(A) Rosenmund reaction (B) Sandmayer reaction (C) Wurtz reaction (D) Friedel craft reaction

4. Compound which gives acetone on ozonolysis(A) CH3 – CH = CH – CH3 (B) (CH3)2C = C(CH3)2 (C) C6H5CH = CH2 (D) CH3CH = CH2

5. Identify the reaction X and the product Y

CH3 – OH – CH3 + X (CH3)3C – OMg – Cl Hydrolysis Y + Mg (OH) Cl(A) X = MgCl2; Y = CH3CH = CH2 (B) X = CH3MgCl; Y = C2H5COCH3

(C) X = CH3MgCl; Y = (CH3)3 C – OH (D) X = C2H5MgCl; Y = (CH3)3C – OH

6. When m-chlorobenzaldehyde is treated with 50% KOH solution, the product (s) obtained is (are)

(A) CH CH

OH OH

OH OH

(B)

OH

COO—

+

OH

CH OH2

(C)

Cl

COO—

+

Cl

CH OH2

(D)

Cl

CH CH

OH OH

Cl

7. A and B in the following are

(A) (B)

(C) (D) A = RR' CH2CN, B = NaOH

8. Reduction of Aldehydes and Ketones to hydrocarbon take place in the presence of(A) Zn amalgam and HCl acid (B) Pd / BaSO4

(C) Anhydrous AlCl3 (D) Ni / Pt

9. Reduction of > C = O to CH2 can be carried out with(A) Catalytic reduction (B) Na / C2H5OH(C) Wolf-Kishmer reduction (D) LiAlH4

SINGLE OBJECTIVE NEET LEVELExercise # 1



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1.

||O

/HO

CHO–Ph 4LiAlH

[X], Product (X) in this reaction is :

(A) (B) (C) (D)

2.

OH/KMnO

.aq.dilCold

4 (Z)

The products of the above reaction is / are :

(A)

OH

CH3

(B)

CH3

O

CH3

(C) (D)

3. What will be the product of the following reaction

HRCO3 ?

(A) (B) Ph

O||

C —CH (C) PhCH(Me)OCOOMe (D) None of these

4. In which of the following reaction deuterium exchange is observed ?

(A) excessH O/OH2

(B)

OH/OD2

(C)

OH/OD2

O|| H

D HD

(D)

OH/OD2

SINGLE OBJECTIVE AIIMS LEVELExercise # 2

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1. Column-I Column-II

(A) (p) 1, 4-addition

(B) (q) Tautomerism

(C) CH3–CH=CH–CH = CH2 (r) AgNO3 / NH4OH

2. Column-I Column-II

(A) (p) Nucleophilic substitution

(B) (q) electrophilic substitution

(C) (r) Dehydration

(D) (s) Nucleophilic addition

3. Match the product of Column- II with the reaction given in Column- I.Column- I Column- II(A) RMgI + Acetonitrile ( NCCH3 ) (p) Alkanone(B) RMgI + Carbon disulphide (q) Ester(C) RMgI.(1eq) + Ethyl chloroformate (r) 1° Alcohol(D) RMgI + Oxirane (s) Dithionic acid

4. Match the column Column I Column II

(A) MeCO(CH2)4COMe

/H)ii(

OH)i( (p)

(B) (CH2)4

OEt (q)

(C) PhCHO + –

3COOCH (r)

OH|

COO—C)Ph( –2

(D) PhCOCOPh OH (s)

Exercise # 3 PART - 1 MATRIX MATCH COLUMN



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1. During reduction of aldehydes with hydrazine andpotassium hydroxide, the first is the formation of

[CBSE AlPMT 2000](A) R CH = N NH2 (B) R C N

(C) C NH2R

O(D) R CH = NH

2. Polarisation of electrons in acrolein may be writtenas [CBSE AlPMT 2000]

(A) CH2

+ -CH CH O

(B) CH2

+ +CH CH O

(C) CH2

+ +CH CH O

(D) CH2

- +CH CH O

3. Reduction by LiAlH4 of hydrolysed product of anester gives [CBSE AlPMT 2000](A) two acids(B) two aldehydes(C) One molecule of alcohol and another of carboxlic

acid(D) two alcohols

4. Benzoic acid may be converted into ethyl benzoateby reaction with [CBSE AlPMT 2002](A) sodium ethoxide (B) ethyl chloride(C) dry HCl, C2H5OH (D) ethanol

5. In the following reaction, product P is[CBSE AlPMT 2002]

R – C – Cl PO

H2

Pd – BaSO4

(A) RCH2OH (B) RCOOH(C) RCHO (D) RCH3

6. In a set of the given reactions, acetic acid yielded aproduct C.

CH COOH + PCl3 5

OBC H6 6

anhy. AlCl3A C H MgBr2 5

Ether C

Product C would be [CBSE AlPMT 2003]

(A) CH3CH(OH)C6H5 (B) CH –C(OH)C H3 6 5

C H2 5

(C) CH3CH(OH)C2H5 (D) CH3COC6H5

7. Which one of the following orders of acidic strengthis correct ? [CBSE AlPMT 2003](A) RCOOH > HOH > HC CH > ROH(B) RCOOH > HC CH > HOH > ROH(C) RCOOH > ROH > HOH > HC CH(D) RCOOH > HOH > ROH > HC CH

8. A and B in the following reactions are[CBSE AlPMT 2003]

R R`CHCN/KCN

AB R

R`C

OH

CH NH2 2

(A) A = RR`CH2CN, B = NaOH

(B) OH

A = RR`C COOH

B=CH3

(C) CN

A = RR`C COOH

B=CH3

(D) CN

A = RR`C OH

B=LiAIH4

9. Which one of the following can be oxidised to thecorresponding carbonyl compound?

[CBSE AlPMT 2004](A) 2-hydroxy propane(B) Ortho-nitro phenol(C) Phenol(D) 2-methyl -2 hydroxy propane

10. In a set of reactions, acitic acid yielded a product D.

CH COOH A B C D3SOCl2 Benzene

anhy. AlCl3

HCN HOH

The structure of D would be [CBSE AlPMT 2005]

(A) COOHC

OH

CH3

(B) CH3C

COOH

OH

CH2

(C) CH3C

OH

CN

CH2

(D) CH3C

CN

OH

Exercise # 4 PART - 1 PREVIOUS YEAR (NEET/AIPMT)

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STRAIGHT OBJECTIVE TYPE1. PhCoCHBr2 OH

A OH

B H

C

The compound ‘C’ is

(A) PhCH(OH)CHO (B) PhCH(OH)COOH (C) PhCOCBr2

H(D) Ph

OC CH2 OH

2. Which stepis not fresh in the following loop?

CH (Br)CH CHO2 2

d alc. KOH

CH =CHCHO2

EtOH, H+

a CH2 CH OH(OE2

b alc. KOH

CH =CHCH(OEt)2 2H O, H2

+

c(A) step - a (B) step - b (C) step - c (D) step - d

3. CH3 COCHO OH

P 3H O

Q, 2Q R, The product R is

(A) CH3 CH(OH)COOH (B) CH3 CHC C

O C

O

O

CH CH3

(C) CH3 CH=CH COOH (D) CH3 CH

O

C

O

CH3

OH

4. CH3 C (CH )2 4 C CH3

O O OH

heat A Ph MgBr B Zn–HgConc.HCl C

The product ‘C’ is

(A) Ph

(B)

Ph O

(C)

Ph

(D)

Ph

5. The structure of major proeduct (pseudoionone) is,

CHO

Geranial

+

O

EtONa/EtOH( 5 C) (Pseudoinone)

(A)

O

H

O

(B)

O

H (C)

O

(D)

O

H

MOCK TEST

PHYSICS

Module-11. Physical World &

Measurements2. Basic Maths & Vector3. Kinematics

Module-21. Law of Motion & Friction2. Work, Energy & Power

Module-31. Motion of system of

particles & Rigid Body2. Gravitation

Module-41. Mechanical Properties

of Matter2. Thermal Properties of Matter

Module-51. Oscillations2. Waves

CHEMISTRY

Module-1(PC)1. Some Basic Conceps of

Chemistry2. Atomic Structure3. Chemical Equilibrium4. Ionic Equilibrium

Module-2(PC)1. Thermodynamics &

Thermochemistry2. Redox Reaction3. States Of Matter (Gaseous &

Liquid)

Module-3(IC)1. Periodic Table2. Chemical Bonding3. Hydrogen & Its Compounds4. S-Block

Module-4(OC)1. Nomenclature of

Organic Compounds2. Isomerism3. General Organic Chemistry

Module-5(OC)1. Reaction Mechanism2. Hydrocarbon3. Aromatic Hydrocarbon4. Environmental Chemistry &

Analysis Of Organic Compounds

BIOLOGY

Module-11. Diversity in the LivingWorld2. Plant Kingdom3. Animal Kingdom

Module-21. Morphology in Flowering Plants2. Anatomy of Flowering Plants3. Structural Organization inAnimals

Module-31. Cell: The Unit of Life2. Biomolecules3. Cell Cycle & Cell Division4. Transport in Plants5. Mineral Nutrition

Module-41. Photosynthesis in Higher Plants2. Respiration in Plants3. Plant Growth and Development4. Digestion & Absorption5. Breathing & Exchange of Gases

Module-51. Body Fluids & Its Circulation2. Excretory Products & TheirElimination3. Locomotion & Its Movement4. Neural Control & Coordination5. Chemical Coordination andIntegration

11th Class Modules Chapter Details

Physics5

Modules

Chemistry5

Modules

Mathematics5

Modules



PHYSICS

Module-11. Electrostatics2. Capacitance

Module-21. Current Electricity2. Magnetic Effect of Current

and Magnetism

Module-31. Electromagnetic Induction2. Alternating Current

Module-41. Geometrical Optics2. Wave Optics

Module-51. Modern Physics2. Nuclear Physics3. Solids & Semiconductor

Devices4. Electromagnetic Waves

CHEMISTRY

Module-1(PC)1. Solid State2. Chemical Kinetics3. Solutions and Colligative

Properties

Module-2(PC)1. Electrochemistry2. Surface Chemistry

Module-3(IC)1. P-Block Elements2. Transition Elements

(d & f block)3. Co-ordination Compound4. Metallurgy

Module-4(OC)1. HaloAlkanes & HaloArenes2. Alcohol, Phenol & Ether3. Aldehyde, Ketone &

Carboxylic Acid

Module-5(OC)1. Nitrogen & Its Derivatives2. Biomolecules & Polymers3. Chemistry in Everyday Life

BIOLOGY

Module-11. Reproduction in Organisms2. Sexual Reproduction inFlowering Plants3. Human Reproduction4. Reproductive Health

Module-21. Principles of Inheritance andVariation2. Molecular Basis of Inheritance3. Evolution

Module-31. Human Health and Disease2. Strategies for Enhancement inFood Production3. Microbes in Human Welfare

Module-41. Biotechnology: Principles andProcesses2. Biotechnology and ItsApplications3. Organisms and Populations

Module-51. Ecosystem2. Biodiversity and Conservation3. Environmental Issues

Physics5

Modules

Chemistry5

Modules

Mathematics5

Modules


12th Class Modules Chapter Details


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