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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
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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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BENZALDEHYDE (C6H5CHO)
Oil of bitter almondsGeneral Method of Preparation :
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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
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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
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