Aldehyde Ketone and Acid

7/27/2019 Aldehyde Ketone and Acid

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Class-XII AldehydesKetonesCarboxylic Acids

Jayanta kumar sahuPGT : ChemistryKendriya Vidyalaya Sangathan Page - 1

ALIPHATIC PORTION

[1] Preparation of Aldehydes and Ketones

(a) From alcoholsPrimary alcohols in presence of oxidizing agents such as anhydrous CrO3 or PCC , or by

catalytic dehydrogenation with Cu at 573 K get oxidised to aldehydes whereas secondaryalcohols results in the formation of ketones.

R CH2 OHAnhydrous CrO 3 / PCC

OxidationR CHOR CHO

Cu / 573 K

Dehydrogenation1o AlcoholAldehyde Aldehyde

2 Cu O2 2 CuO+

R CH2 OH + CuO Cu OH2R CHO + +

Details of dehydrogenation

(b) From alkenesThe alkenes on treatment with ozone followed by reductive cleavage (by Zn dust and water)results in the formation of aldehydes whereas substituted alkenes form ketones.

CH CH2R O3+

O O

C C

OR

H

H

H

Zn / H2OH C

O

HR C

O

H +Alkene

Ozonide

Aldehydes

CH CH2R

R

O3+

O O

C C

OR

R

H

HZn / H2O

R C

O

R + H CO

H

Ketone Aldehyde

(c) From alkynesEthyne reacts with water in the presence of mercuric sulphate and sulphuric acid to yieldaldehyde i.e. ethanal. Other alkynes give ketones.

CH CH +HgSO 4H2SO4

H OHCH2 CH

O H

TautomerisationCH3 C

O

HEthyne Ethanalenol ( Unstable )

C CHR + H OH+ HgSO 4

H2SO4R C

O H

CH2

TautomerisationR C CH

3

O

Ketone

[2] Preparation of Aldehydes only

(a) From acid chlorides [ Rosenmund reduction ]

R C

O

ClH2

Pd - BaSO 4R C

O

H

Acid chloride Aldehyde


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(b) From Nitriles [ Stephen Reduction ]The reaction of alkanenitrile with HCl in the presence of anhydrous stannous chlorideyields corresponding imine, which on hydrolysis give corresponding aldehyde.

R C NSnCl 2

HClR CH NH

imine

OH3+

R CHO

(c) From Acid derivatives

AcidLiAlH4

AldehydeLiAlH4 1o Alcohol

In order to prevent formation of alcohol, we use a derivative of carboxylic acid ( Acidchloride, Ester and Nitrile ) that is more easily reduced and an derivative of aluminiumhydride ( DIBAL-H ) that is less reactive than lithium aluminium hydride.

AlH

Diisobutylaluminium hydride ( DIBAL-H ) is less reactive than LiAlH4, because

it is much more sterically hindered and ,therefore, have difficulty intransferring hydride ions.

R C NAl H (i-Bu) 2 i.e. DIBAL-H

OH2

R CHO

R C

O

OR1

Nitrile

Ester

Al H (i-Bu) 2 i.e. DIBAL-HOH2

R CHO

R C

O

ClAcid chloride

Al H (i-Bu) 2 i.e. DIBAL-HOH2

R CHO

[3] Preparation of Ketones only

(a) From Acid chlorides

Treatment of acyl chlorides with dialkylcadmium, prepared by the reaction of cadmiumchloride with Grignard reagent, gives ketones.

R Mg X CdCl 2 R2Cd 2 Mg(X)Cl2 + +

R1 C

O

Cl2 + R2Cd R1 CO

R2 + CdCl 2(b) From Nitriles

Treatment of nitrile with Grignard reagent followed by hydrolysis yields a ketone.

R Mg XR1 C N +R1 C

NMgBr

R

OH3+

R1 C

O

R

AROMATIC PORTION(a) From alcohols

CH2

OHK2Cr2O7 / H

+

CHO

C CH3

O

K2Cr2O7 / H+

CH CH3

OH

CH

OH

C

O

K2Cr2O7 / H+


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(b) From acyl chloride ( Rosenmund reduction )

CCl

O

H2

Pd - BaSO 4

CH

O

Benzoyl chloride Benzaldehyde

(c) From nitriles ( stephen reaction )

SnCl 2

HCl

C NCH NH

BenzonitrileImine

OH2 C H

O

(d) From Methyl benzene ( Etard reaction )

CH3

CrO 2Cl 2CS2

+

Toluene

CH ( OCrOHCl 2 )2

Chromyl chloride Chromium complex

CH

O

OH3+

Benzaldehyde

CH3

+ CrO3 ( CH3CO ) 2O+Chromic oxide Acetic anhydride

273 K - 283 KCH ( OCOCH 3 )2

CH

O

OH3+

Benzylidene diacetateToluene

Not Etard reaction

(e) From benzene ( Gatterman - Koch reaction )An aldehyde group is directly introduced by treating benzene with carbon monoxide and

hydrogen chloride in the presence of aluminium chloride as a catalyst.

+ CO HClAlCl 3

+CHO

+ HCl

This is an electrophilic substitution reaction ( modified Friedel-crafts reaction ), wherethe most likely electrophile is acylium ion.

CO + HCl + AlCl 3 C O

H

+ + AlCl 4

(f) From Toluene by side chain chlorination

CH3

Cl2

/ hCHCl 2

373 K

OH2CHO

Benzalchloride

(g) From Grignard reagent

MgBr

R C N+Ether

CCH3

NMgBr

OH3+ C

CH3

O


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Properties of Aldehydes and KetonesNucleophilic Addition Reaction

C O

R1

R2

+ Nu C

Nu

R1O

R2

Slow H

+

FastC

Nu

R1OH

R2

[1] Addition of HCN in presence of a base

C

O

R1 R2 + HCNBase

C

OH

R1 R2

CN Cyanohydrin

Base is used to generate Cyanide ion : HCN + OH CN OH2+

Strong Nucleophile

[2] Addition of Sodium hydrogensulphite

C

O

R1 R2 + NaHSO 3 C

OSO2H

R1 R2

ONa

H+ Transfer C

OSO 2Na

R1 R2

OH

Bisulphite addition product

This bisulphite addition product is formed by all aldehydes and only by methyl ketones.The other ketones due to decrease in electrophilicity of carbonyl carbon and also becauseof steric factors due to alkyl groups, do not react with sodium bisulphite.

This reaction is used to separate and purify aldehydes andketones, because aldehydes and ketones may be recovered from their suphite adducts bywarming them up with sodium carbonate solution.

C

OSO 2Na

R1 R2

OH

Na2CO3C

O

R1 R2 + Na2SO3 NaHCO 3+

[3] Addition of Grignard Reagent

R Mg Br C

O

+ +

C

O Mg Br

R

+

OH2R C OH

Alcohol

+ Mg Br OH

Carbonyl compound

Formaldehyde results in the formation of 1o alcohol

Aldehyde ( Other than Formaldehyde ) results in the formation of 2o alcohol

Ketones result in the formation of 3o alcohol

[4] Addition of AlcoholsAddition of alcohols ( Weak nucleophile ) to aldehydes in acidic medium first formshemiacetals which on addition of second molecule of alcohol results in the formation ofacetals.

Addition of alcohols to ketones to form hemiketals and ketals does not occur readilybecause of the steric hindrance.

R C

O

H R1 OH+H

+R C

OH

OR1

H

R1 OHR C

OR1

OR1

HHemiacetal AcetalAldehyde


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R C

O

R R1 OH+H

+

R C

OH

OR1

R

R1 OHR C

OR1

OR1

RKetone

HemiketalKetal

Alcohol

C O

R

R

CH2

CH2

O

OC

R

R

+ HCl gasdil. HCl

CH2

CH2

OH

OH

Ethyleneglycol ketal

Acetals and ketals are hydrolysed with aqueous mineral acids to yield correspondingaldehydes and ketones.

Nucleophilic Addition - Elimination Reaction

Addition of ammonia and its derivatives

C O

R

R

+ NH2 ZH

+

C N

R

R

Z + OH2

C

O

R R

H+

C

OH

R R+

NH2 Z

x x

C

R

R

OH

N+

H

H

Z H+

C

R

R

OH

N

H

ZOH2

C

R

R

N Z

C O

R

R

H2 NH+Ammonia Imine

C

R

R

N H

C O

R

R

+ H2 NR CR

R

N R

Amine Substituted i mine

( Schiff's base )

C O

R

R

+ H2 NOH

Hydroxyl amine

C

R

R

N OH

Oxime

C O

R

R

+ H2 N NH2 CR

R

N NH2Hydrazone

NHNH

H

Phenylhydrazine

C O

R

R

+ NHNC

R

RPhenylhydrazone

C O

R

R+ NHN

H

HNO2

O2N

NHNC

R

R

NO2

O2N

2, 4 - dinitrophenylhydrazine2, 4 - dinitrophenylhydrazone

( Yellow, Orange or Red solid )

C O

R

R

+ C NH2NH

O

NH

HSemicarbazide

C NH2NH

O

NC

R

R Semicarbazone

Hydrazine


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Reduction Reaction[1] Catalytic Reduction

R C

O

HH2 / Pt ( Primary alcohol )

AldehydeR CH2 OH

R C

O

R H2 / Pt R HC OH

RKetone( Secondary alcohol )

O

OH

H2 / Pt

( Secondary alcohol )

LiAlH4 / NaBH 4

LiAlH4 / NaBH 4

[2] Wolff - Kishner Reduction

C O

R

R

+ H2 N NH2 CR

R

N NH2Hydrazone

Hydrazine

KOH / ethylene glycol

HeatR CH2 R + N2

Alkane

[3] Clemmensen Reduction

R C R

O

Zn - Hg

Conc. HCl +R CH2 RAlkane

OH2

Carbonyl compounds

Oxidation Reaction

R C CH3

O

R C H

O

Ketone

Aldehyde

Strong oxidising agent

Strong oxidising agent

RCOOH HCOOH+

RCOOH

Mild oxidising agent

Mild oxidising agentRCOOH

No product

The oxidation of ketone required cleavage of carbon - carbon bond, which can not break by

mild oxidising agents such as Tollen's reagent and Fehling's solution.

O

Cyclohexanone

Tollen's reagent

Fehling's solutionNo product

K2Cr2O7 / H+

OR KMnO 4 / H+

OR CrO 3 / H+

( CH2 )4

COOH

COOH

Hexanedioic acid ( Adipic acid )Tollen's Test

Aldehyde + Tollen's reagent Silver mirror

Ketone No silver mirror+ Tollen's reagent

To aqueous silver nitrate,a drop of dilute sodium hydroxide is added, forming a brownprecipitate of silver oxide.

Concentrated ammonia is then added until the precipitate just dissolves

So Tollen's reagent is ammonical silver nitrate i.e.

2 AgNO 3 2 NaOH+ Ag2O 2 NaNO 3 OH2+ +

Ag2O + 2 NH 3 NaNO 3+ + OH2 [ Ag ( NH 3 )2 ] NO 3 2 NaOH

+[ Ag ( NH 3 )2 ] NO 3

RCHO 3 OH RCOO 2 H2O 2 e+ + +

[ Ag ( NH 3 )2 ]+

+ e

Ag 2 NH 3+ X 2

RCHO + 3 OH + 2 [ Ag ( NH3 )2 ]+

RCOO + 2 H2O + 4 NH 3 + 2 Ag

Silver mirror


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Fehling's TestFehling solution is a mixture of alkaline copper(II) sulphate solution and sodium poatssiumtartarate (Rochelle salt ) Aldehyde + Fehling's reagent

Ketone + Fehling's reagent No Reddish Brow n precipitateReddish Brow n precipitate

Aromatic aldehyde + Fehling's reagent No Reddish Brow n precipitate

RCHO 3 OH RCOO 2 H2O 2 e+ + +

2 Cu 2 OH Cu2O OH2++ 2 e

+

2+

RCHO + 2 Cu2+

+ 5 OH

RCOO

+ 3 H2O + Cu2O Reddish Brown precipitate

Hydroxyketones give positive Tollen's and Fehling test, because inhydroxyketones,thesecondary alcoholic group gets oxidised to ketonic group.

CH3 CH2 CH

OH

C CH3

O3-Hydoxypentan- 2-one( hydroxyketone )

CH3 CH2 C

O

C CH3

OPentane- 2, 3 - dione

+Fehling's reagentTollen's reagent

2 H2O + 4 NH 3 + 2 AgSilver mirror

3 H2O

+Cu

2O

Reddish Brow n precipitate

Idoform TestThe reaction is used to detect the and groups in an organiccompound. The organic compounds containing the above groups when treated withhalogen in presence of an alkali results in the formation of Chloroform,bromoform oridoform. Idoform is a yellow solid.

CH3 C

O

CH3 CH

OH

R C CH3

O

+ NaOIsodium hypoiodite

i.e. I 2 & NaOHR C

O

ONa + CHI 3 Idoform( Yellow ppt. )

CH3CH

OH

R + I2 2 HI

CH3C

O

R+I2 NaOH

R C

O


This oxidation does not affect a carbon- carbon double bond, if present in the molecule.

CH3 CH C

CH3

C CH3

O

+ NaOIsodium hypoiodite

CH3 CH C

CH3

C

O


The iodoform reaction is given by:

(1) Ethanol [ The only 1o alcohol ]

(2) All secondary alcohols with group. (3) Acetaldehyde [ the only aldehyde ]CH3 CH

OH

CH3 C

O

CH3 C

O

group is necessary for idoform reaction, because the group is an

electron withdrawing group, which makes the H of methyl group acidic in nature.

C

O

The conjugate base, after removal of H, become resonance stabilised.

C CH

O

H B C CH

O

C CH

O

(4) All methyl ketones [ aliphatic and aromatic ] with group.


8/15



Aldol condensationAldehydes and ketones having at least one H undergo a reaction in presence of dilutealkali as catalyst to form hydroxy aldehydes or hydroxy ketones

[ ALDOL = ALD ehyde + alcoh OL ]

2 CH 3CHOdil NaOH

CH3 CH CH2 CHO

OH

OH2

CH3 CH CH CHO

3 -Hydroxybutanal [ Aldol ] But-2-enal

CH3 C

O

H

H CH2 C H

O

+dil NaOH

CH3 CH CH CHO

OH H

OH2

CH3 CH CH CHO

CH3 C

O

CH3

H CH2 C CH3

O

+dil NaOH

CH3 C CH C

OHH

O

CH3

CH3

OH2

Ethanal

CH3 C CH3

OBa(OH) 2

2 CH3 CH CH2 C

OH

CH3

O

CH3

OH2CH3 C CH C

CH3

O

CH3

Propanone

4-Hydroxy- 4-methylpentan- 2-one

4-Methylpent- 3-en- 2-one[ Ketol ]

CH3 C CH C

CH3

O

CH3

When aldol condensation is carried out between two different aldehydes or ketones, it is

called cross aldol condensation.

CH3CHO

CH3CH2CHO

1. NaOH

2. +

CH3 CH CH CHO + CH2 CH C CHOCH3

CH3

Selfcondensationproduct

H3C CH C CHO

CH3

+ CH2 CH CH CHOCH3MixedcondensationproductPent- 2-enal2-Methylbut- 2-enal

But- 2-enal 2-Methylpent - 2-enal

C

O

H

CCH2

O

H

Benzaldehyde

No hydrogen

+

Acetophenone

Having hydrogen

CH

OH

CH

H

C

O

CH CH C

O

dil NaOH

OH2

1,3-diphenylprop-2-en-1-oneCannizzaro Reaction

Aldehydes having nohydrogen,when treated with conc. alkali, undergo self oxidationand reduction [ disproportionation / dismutation / auto oxidation-reduction ] reaction.

H C H

O

2 Conc. NaOH CH3OH HCOONa+Methanal Methanol Sodium methanoate

C

O

HConc. NaOH

2

Benzaldehyde

CH2 OH C

O

ONa+

Benzyl alcohol Sodium benzoate


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Electrophilic substitution reaction.Carbonyl groups act as deactivating and meta - directing group.

C

OR

R = H : aldehydeR = alkyl : Ketone

Cl 2 / AlCl 3

HNO 3 / H2SO4

H2SO4 / SO 3

C

O

R

Cl

C

O

R

NO2

C

O

R

SO3H

40%solutionofform

aldehydeisknownasform

alin.

ALIPHATIC PORTION

Preparation of Carboxylic Acids[a] From alcohol and aldehyde

R C H

O

RCH 2OH RCOOH1. alkaline KMnO 4

2. H3O+

1o alcohol

CH3 (CH2)8CH2OH

1-Decanol

CH3 (CH2)8COOH

Decanoic acid

1. alkaline KMnO 4

2. H3O+

Aldehyde

RCOOHStrong oxidising agent

Mild oxidising agentOR[b] From Grignard reagents

C O

O

R MgBr +- +

RC

O MgBr

O

Dry etherH3O

+

RCOOH

Dry ice

- +

[c] FromAcid derivatives

Acid chloride

Acid anhydride

Ester

Amide

R C

O

ClOH2

ClH+RCOOH

R C

O

OC R1

O

OH2RCOOH + R1COOH

R C

O

OR' RCOOH R' OH+H3O

+NaOH

RCOONa R' OH+H3O

+

RCOOH( Saponification)

R C

O

NH2

H3O+

RCOOH + NH3R C N

Nitrile

H3O+


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AROMATIC PORTION

CH2 R

Alkyl benzene

KMnO 4 - KOH

COOKH3O

+ COOH

[ The entire side chain is oxidised to the carboxylic acid irrespective of length of side chain ]

CONH 2

Benzamide

H3O+

COOH

NH3+

C

O

OC

CH3

O

H3O+

OH2

Benzoic ethanoic anhydride

COOH

+ CH3COOH

Benzoic acid

Benzoic acid

Benzoic acidEthanoic acid

C

O

OC2H5

Ethyl benzoate

COOH

+ C2H5OH

Properties of Carboxylic Acid[1] Acidity

Carboxylic acids dissociate in water to give resonance stabilised carboxylate anion.

R C

O

OH + OH2 R CO

O

R C

O

O

+ H3O+

2 RCOOH + 2 Na 2 RCOONa H2+

RCOOH NaOH+ RCOONa OH2+RCOOH + NaHCO 3 RCOONa + OH2 + CO2 [ Test for carboxylic group ]

[ Brisk effervescence ]

CH2 CH COOH CH3 CH2 COOHAcidity of >

SP2

SP3

C

O

OH CH2

C OH

O

>

SP2

SP3

carbon is more electronegative than carbon,SP2 SP3

[2] Esterification

CH3 C OH

O

H O CH3+Acid Alcohol

CH3 C O

O

CH3H

+

+ OH2Ester

CH3 C OH

O

+ OHH

+

OC

O

CH3 + OH2Phenyl ethanoateEthanoic acid Phenol

The water should remove from the mixture, because ester may undergohydrolysis.


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H2SO4 /

or P2O5 /

[3] Formation of Acid anhydride

CH3 C

O

OHC CH3

O

OH

CH3 C

O

O

C CH3

O

+

Ethanoic acid Ethanoic anhydride

+ OH2

[4] Formation of Acid chloride

CH3 C

O

OH PCl 5

PCl 3

SOCl 2

+ClHPOCl 3CH3 C

O

Cl + +

CH3 C

O

OH3 + CH3 C

O

Cl3 + H3PO 3

CH3 C

O

OH + CH3 C

O

Cl + SO2 + ClH

[5] Formation of Acid amide

CH3 C

O

OH + NH3 CH3 C

O

O NH4+

CH3 C

O

NH2

Ammonium ethanoate Ethanamide

COOH

+ NH3COO NH 4

OH2

OH2

CONH 2

Amm.benzoate Benzamide

COOH

COOH

+ NH3 COO NH4

COO NH4

- +

- + 2 H2O

CONH2

CONH2

Strong heating

C

C

NH

O

OPhthalic acid Ammonium phthalate Phthalamide

Phthalimide

NH3

[6] Formation of Alcohol [ Reduction ]

R C

O

OH

LiAlH4 / Ether

H3O+

R CH2 OH[ The reaction involve hydride transferand causes reuction of carbonyl group ]

R C

O

OHH3O

+

B2H6R CH2 OH

[ Diborane is better for this process, becauseit does not easily reduce ester,nitro and halogroups]

Sodium borohydride does not reduce the carboxyl group.[7] Formation of Alkane [ Decarboxylation ]

R C

O

ONa + NaO H

CaORH + Na2CO3

AlkaneSodium salt of carboxylic acid

[ NaOH & CaO in the ratioof 3:1 is known as sodalime ]

Kolbe electrolysis

RCOONaElectrolysis

R R + CO2 + NaOH H2+At anode At cathode


12/15



[8] Hell - Volhard - Zelinsky Reaction ( HVZ reaction )

R CH2 COOH

Having - hydrogen

(i) X2 / Red phosphorous

(ii) H 2O

R HC COOH

X

X : Cl , Br

If two hydrogens are present, both of them may be substituted by halogen.

[9] Ring substitution reactionCarboxylic group act as deactivating and meta directing group.

C

OHO

Cl 2 / AlCl 3

HNO 3 / H2SO4

H2SO4 / SO3

HOOC

Cl

HOOC

NO2

HOOC

SO3H

ExplanationsDue to polarity of carbonyl group to ward oxygen,the intermolecular association of carbonylcompounds occurs which makes the boiling point of carbonyl compounds higher than the

corresponding alkane of comparable mass.However carbonyl compounds can not form hydrogen bonding with

each other and their boiling points are lower compared to alcohol (of comparable mass)

The lower members of aldehydes and ketones are soluble in water in all proportions,because they associate with water molecules through hydrogen bonding.

The reaction of Grignard reagent with nitriles is considered to be the best method for thepreparation of carbonyl compounds, because, in the first stage of addition an imine isformed as an intermediate product. The imine is then isolated and hydrolysed to give acarbonyl compound as the final product.

Reaction of Grignard reagent with acid chloride and esters produce carbonylcompounds,but the reaction does not stop at this stage and proceeds further with another

molecule of Grignard reagent to give corresponding alcohol as the final product.Grignard reagent and dialkyl cadmium both are organometallic compounds, but reaction ofacid halides with[a] Grignard reagent is not satisfactory method for the preparation of ketones.[b] Dialkylcadmium is a satisfactory method for the preparation of ketones.Because, in case of dialkylcadmium, due to less reactivity of cadmium, reaction with acidchloride occurs only upto the formation of ketone. The reaction of Grignard reagent doesnot stop after formation of ketone, since magnesium is more reactive metal,and proceedsfurther to form tertiary alcohol.

Aryl ketones do not undergo addition of alcohol to form hemiacetals and ketals because ofsteric factor.

CR

O

+ R' OH

R = alkyl / aryl

H

+

No reaction


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Aryl ketones do not give addition product with sodium bisulfite due to steric factor.

C R

O

+ NaHSO 3 No reaction

R = alkyl / aryl

The order of reactivity of aldehydes and ketonestoward nucleophilic addition reaction: C

O

H HC

O

R HC

O

R R

Sterically the presence of two relatively large substituents in ketones hinder the approachof nucleophile to carbonyl carbon than in aldehydes.

Electronically two alkyl groups in ketone reduce the electrophilicity of the carbonylmore effectively than in aldehyde.

NH2 NH C

O

NH2x xx x

[Semicarbazide]

Involved in the formationof semicarbazone

The right side -NH2 group is in conjugation with electron

withdrawing carbonyl group and acquires positive charge and notin a position to act as the nucleophile, so does not involvein the formation of semicarbazone.

O

Cyclohexanone

OH

CN

O

CH3 CH3

CH3

HCNHCN No product

cyanohydrin

2, 4, 6-trimethylcyclohexanoneIn 2,4,6-trimethylcyclohexane, the three methyl groups will increase the electron densityon the carbonyl carbon atom and the nucleophile attack does not seem to be feasible.Moreover,the two methyl substituents at the ortho position will also hinder the attack of

nucleophile CN ion on the carbonyl group.

Upon heating , formic acid loses a molecule of water and gets dehydrated to give carbonmonoxide. Therefore it does not form anhydride upon heating.

HCOOH H2OCOHeat

+Phenoxide ion has more number of resonating structures than carboxylate ion, butcarboxylic acid is a stronger acid than phenol. Because, in carboxylate ion the negative

charge is dispersed on two electronegative oxygen atoms while incase of phenoxide ion,there is only one oxygen atom to disperse the negative charge.

Benzaldehyde and other aromatic aldehydes form silver mirror with Tollen's reagent butfail to react with fehling's solution and Benedict's solution. Due to resonance, the electrondensity on the carbonyl carbon atom inbcreases, as a result the CH bond becomesstronger. It can be oxidised to C OH with strong oxidising agents like Tollen's reagent

( EoAg2+|Ag = +0.8 V ) but not with weaker Fehling's or Bendedict's reagent

( Eo Cu2+ |Cu = +0.34 V )

In Fehling solution , copper sulphate forms a soluble complex of Cu2+ ions with tartarate

ion of the Rochelle's salt. The complex provides the Cu2+ ions and also checks the

precipitation of copper hydroxide in the reaction.


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Predict the ProductsOH

PCC , CH 2Cl 2O

Cyclohex- 2-en- 1-ol? Cyclohex- 2-en- 1-one

+ H5C2C

O

Cl ?Anhy. AlCl 3

CS2

( C6H5CH2)2Cd 2 CH3COCl+ ?CH3 C CH

Hg2+

H2SO4 ?CH3 NO2

1. CrO 2Cl 2

2. H3O+ ?

CC2H5

O

CCH3

O

CH2

CH3

C

CH3

O

OHC NO2

OHONH 2

H+

?+

O

NH NO2

O2N

NH2+ ?

R CH CH CHO NH2 C

O

NH NH2+ H+

?C

CH3

O

CH3CH2NH2+ H+

N OH

NH NO2

O2N

N

R CH CH CH N NH C

O

NH2

C

CH3

N CH2CH3

?

CH2 CH3KMnO 4

KOH , Heat ?

COOH

COOH

SOCl 2

Heat ?

CHONH2 C

O

NH NH2 ?O

CHO

[ Ag(NH 3)2]+

?

COOK

COCl

COCl

N NH C

O

NH2CH

O

COO


15/15



CHO

COOH

NaCN / HCl

?

C6H5CHO CH3CH2CHOdil. NaOH+ ?

CH3COCH 2COOC 2H5(i) NaBH 4

(ii) H+

OHCrO3

?

?

COOH

CH

OH

CN

H5C6 CH C

CH3

CHO

CH3 CH

OH

CH2 COOEt

O

(i) O3

(ii) Zn - H 2O

O

?

CHO

+ C6H5MgBrH3O

+ CHC6H5

OH

?

[ Ag(NH 3)2]+

OH-

CHO

+ + ?COO

-

CHO

+ NH2 C

O

NH NH2 ?CH NHCONH 2

C O

H

H OC 2H5+

H OC 2H5 ? CH

OC2H5

O C2H5

O

+dil. NaOH

OH

O

?

O

O

O

Raney Ni / H 2

NaBH 4 / CH 3OH

OH

?

?OH

CH C6H5(i) O3

(ii) Zn / H 2O?

O

C6H5CHO+

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Aldehyde Ketone and Acid