Aldehydes & Ketones

Aldehydes are compounds having general formulaH

CR O R= H, CH 3, C2 H5, C6 H5, etc…

Slide 2Ketones are compounds having general formulaR C

O

R R=CH 3,C2H5, C6H5 etc...

H

CR O R= H, CH 3, C2 H5, C6 H5, etc…

IUPAC names of AldehydesFormula Common Name IUPAC NameHCHO Fomaldehyde MethanalCH3CHO Acetaldehyde Ethanal

Slide 3

CH3CHO Acetaldehyde EthanalCH3CH2CHO Propionaldehyde PropanalCH3CH2CH2CHO Butyraldehyde Butanal(CH3)2CHCHO Isobutyraldehyde 2-Methylpropanal

IUPAC names of AldehydesFormula Common Name IUPAC NameCH2=CH-CHO Acrolein Prop–2–enalCH3CH=CH-CHO Crotonaldehyde But-2-enal

Slide 4

CH3CH=CH-CHO Crotonaldehyde But-2-enalC6H5CH=CH-CHO Cinnamaldehyde 3-Phenylprop-2-enalC6H5CHO Benzaldehyde BenzaldehydeC6H4(OH)CHO Salicyaldehyde 2-Hydroxybenzaldehyde

IUPAC Names of KetonesFormula Common Name IUPAC NameCH3COCH3 Acetone PropanoneCH3COCH2CH3 Ethyl methyl ketone Butanone

Slide 5

CH3COCH2CH3 Ethyl methyl ketone ButanoneCH3CH2COCH2CH3 Diethyl ketone Pentan-3-oneCH3COCH2CH2CH3 Methyl propyl ketone Pentan-2-oneC6H5COCH3 Methyl phenyl ketone orAcetophenone 1-phenylethanoneC6H5COC6H5 Diphenyl ketone orBenzophenone Benzophenone

Structure of Carbonyl groupC O

Sp2 - hybridised

C O120o

120o

Slide 6The carbon- oxygen double bond is polarized due to higherelectro negativity of oxygen than carbon. C+-O-

C O

Sp2 - hybridised

C O120o

120o

C ONucleophile

Electrophile

Hence

From oxidation of primary and secondary alcoholsR C

H

OH

H

PCC

[O]R C

OH

H

OH R C

H

O +H2O

Slide 8

R C

H

OH

H

PCC

[O]R C

OH

H

OH R C

H

O +H2O

R-CH(OH)-R’ KMnO4/KOH R-CO-R’ + H2O

By dehydrogenation of alcoholsR C

H

OH

H

Copper

300oCR C

H

O + H2

Slide 9

R C

H

OH

H

Copper

300oCR C

H

O + H2

R-CH(OH)-R’ Cu/573K R-CO-R’ + H2O

From alkene by ozonolysisR CH CH2 + O3

Zn

H2OR C

H

O + CH2OCH2

OO

CH

O

R

Slide 10

R CH CH2 + O3Zn

H2OR C

H

O + CH2OCH2

OO

CH

O

R

From Acyl ChlorideR C

O

Cl R C

O

H + HClH2

Pd - BaSO4

140oC

By Rosenmund reduction

Slide 11R C

O

Cl R C

O

H + HClH2

Pd - BaSO4

140oC

From Nitrile by Stephen’s ReductionR C N

SnCl2

+HClR CH NH

H2O

H+R C

H

O + NH3

Slide 12

R C NSnCl2

+HClR CH NH

H2O

H+R C

H

O + NH3

Preparation of Benzaldehyde fromTolueneCH3 CrO2Cl2

CS2

CHO+H2O

Etard's Reaction

Slide 13

CH3 CrO2Cl2

CS2

CHO+H2O

Etard's Reaction

By Gattermann – Koch reaction.

Slide 14C6H6 + CO + HCl Anh AlCl3/CuCl C6H5CHO

Dry distillation of calium salts give aldehyde and ketones.Calcium formate – FormaldehydeCalcium formate and calcium acetate - AcetaldehydeCalcium formate and calcium benzoate - BenzaldehydeCalcium acetate - AcetoneCalcium benzoate - BenzophenoneCalcium benzoate and calcium acetate - AcetophenoneSlide 15

Dry distillation of calium salts give aldehyde and ketones.Calcium formate – FormaldehydeCalcium formate and calcium acetate - AcetaldehydeCalcium formate and calcium benzoate - BenzaldehydeCalcium acetate - AcetoneCalcium benzoate - BenzophenoneCalcium benzoate and calcium acetate - Acetophenone

From nitrile and Grignard reagentR C N R

-| Mg

+x R C

R'

N. Mgx2 H2O

H+R C O

R'

+ NH3

Dry

Ether+ Mg

X

OH

Slide 16

R C N R-| Mg

+x R C

R'

N. Mgx2 H2O

H+R C O

R'

+ NH3

Dry

Ether+ Mg

X

OHR-MgX + HCN dry ether R-CH=NMgX H2O/H+ R-CHO

Ketones from Acyl chloride and dialkylcadmium2 R' C

O

Cl + R2Cd 2 R' C

O

R + CdCl2

Slide 17

2 R' C

O

Cl + R2Cd 2 R' C

O

R + CdCl2

Aromatic ketones from Benzene by Friedel – CraftreactionR C

O

ClC R

O

+ HClAnhydrous

AlCl3

Slide 18

R C

O

ClC R

O

+ HClAnhydrous

AlCl3

• Physical state: HCHO – Gas, Up to C13 are liquids and higherones are solids.• Odour : Lower aldehydes have unpleasant odour where ashigher ones have pleasant odour.• Boiling points: These compounds have higher boiling pointsthan ethers and hydrocarbons due to dipole interactions butlower boiling points than that of alcohols due to the absenceof intermolecular hydrogen bonding.

Physical properties of Aldehydes and ketones

Slide 19

• Physical state: HCHO – Gas, Up to C13 are liquids and higherones are solids.• Odour : Lower aldehydes have unpleasant odour where ashigher ones have pleasant odour.• Boiling points: These compounds have higher boiling pointsthan ethers and hydrocarbons due to dipole interactions butlower boiling points than that of alcohols due to the absenceof intermolecular hydrogen bonding.

Reactions of Aldehydes and Ketones(i) Nucleophillic additiona

Cb

O

Planar

a

C

O

b

Nu

H+

a

C

OH

b

Nu

+ Nu

Tetrahedral intermediate Addition Product

slowfast

Slide 20

aC

bO

Planar

a

C

O

b

Nu

H+

a

C

OH

b

Nu

+ Nu

Tetrahedral intermediate Addition Product

slowfast

Reactions of Aldehydes and KetonesWith HCNBoth aldehydes and ketones react with HCN to form additionproduct Cynohydrin (in presence of a base)

HCN + OH- CN

- + H2O

C O

CNC

O

CN

H+

TetrahedralCyanohydrinIntermediate

COH

CN

Slide 21

HCN + OH- CN

- + H2O

C O

CNC

O

CN

H+

TetrahedralCyanohydrinIntermediate

COH

CN

Reactions of Aldehydes and KetonesWith NaHSO3

Bisulphite addition CompoundAll aldehydes react with NaHSO3 to form a white crystallinesolid, bisulphite addition compound. Many ketones also react.But acetophenone does not react with NaHSO3 due to stearichindrance.

C O

+ Na+ SO

-3 H C

O Na

SO3HC

OH

SO3Na

Proton Transfer

Slide 22

With NaHSO3

Bisulphite addition CompoundAll aldehydes react with NaHSO3 to form a white crystallinesolid, bisulphite addition compound. Many ketones also react.But acetophenone does not react with NaHSO3 due to stearichindrance.

C O

+ Na+ SO

-3 H C

O Na

SO3HC

OH

SO3Na

Proton Transfer

Reactions of Aldehydes and KetonesWith alcoholsOnly aldehydes react with alcohols in presence of dry HCl toform acetals.

Slide 23R C

H

Odry HCl

R C

HOR '

OR '+H2O2 R ' OH

acetal

Reactions of Aldehydes and KetonesWith alcoholsKetones react only with Ethylene Glycol to form cyclic product

C OR

R

CH2 OH

CH2 OH

RC

R

O

O

CH2

CH2

+H 2O

Ethylene Glycol Ketal

dry HCl

Slide 24

C OR

R

CH2 OH

CH2 OH

RC

R

O

O

CH2

CH2

+H 2O

Ethylene Glycol Ketal

dry HCl

Reactions of Aldehydes and KetonesWith ammonia derivativesWhere Z=OH, NH2, C6H5NH, NHCONH2 alkyl, aryl NH2 Z

Slide 25C O

NH2 Z COH

NH Z

C N Z +H2O

Reactions of Aldehydes and Ketones• NH2-NH2 CH3CH=N-NH2 Hydrozone• NH2-OH CH3CH=N-OH Oxime• NH2-NHC6H5 CH3CH=N-NHC6H5 Phenyl hydrozone• NH2NHCONH2 CH3CH=N-NHCONH2 Semicarbazone

Slide 26

• NH2-NH2 CH3CH=N-NH2 Hydrozone• NH2-OH CH3CH=N-OH Oxime• NH2-NHC6H5 CH3CH=N-NHC6H5 Phenyl hydrozone• NH2NHCONH2 CH3CH=N-NHCONH2 Semicarbazone

Reactions of Aldehydes and KetonesMechanism

COH

N - Z

H

C O

: NH2 Z CO

-

N

H

HZ

H+ Transfer

Unstable

COH

N Z

H

C N Z +H2O Slide 27

COH

N - Z

H

C O

: NH2 Z CO

-

N

H

HZ

H+ Transfer

Unstable

COH

N Z

H

C N Z +H2O

Reactions of Aldehydes and KetonesOxidation:Aldehydes readily get oxidized to give CarboxyacidsR C

H

O[O]

Na2Cr2O7 + H2SO4

R COOH

Slide 28R C

H

O[O]

Na2Cr2O7 + H2SO4

R COOH

Reactions of Aldehydes and KetonesWith Tollen’s reagent

R C

H

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

- RCOO + 2 Ag + 2H2O + 4NH3

Silver Mirror

Slide 29

R C

H

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

- RCOO + 2 Ag + 2H2O + 4NH3

Silver Mirror

Reactions of Aldehydes and KetonesWith Fehling solution

Slide 30R C

H

O + 2Cu2+

+5OH RCOO + Cu2O +3H2O

Red ppt

Reactions of Aldehydes and KetonesOxidation of Ketones:In presence of strong oxidising agents at high temperatureketones get oxidized . Their oxidation involves C-C bondcleavage. A mixture of Carboxylic acids having lesser number ofcarbon atoms formed.

Slide 31

Oxidation of Ketones:In presence of strong oxidising agents at high temperatureketones get oxidized . Their oxidation involves C-C bondcleavage. A mixture of Carboxylic acids having lesser number ofcarbon atoms formed.CH3 C

O

CH3 CH3COOH + CO2 + H2OEx:alkaline

KMnO44[O]

Reactions of Aldehydes and KetonesReduction: Aldehydes and Ketones are reduced to primary andsecondary alcohol by using LiAlH4 /NaBH4

R C

H

OLiAlH4

THFR CH2 OH

Primary Alcohol

LiAlH4

THFR C

H

OH

R

Secondary Alcohol

R C

O

R Slide 32

R C

H

OLiAlH4

THFR CH2 OH

Primary Alcohol

LiAlH4

THFR C

H

OH

R

Secondary Alcohol

R C

O

R

Reactions of Aldehydes and KetonesReduction to Hydrocarbons (Clemmensen reduction)R C

H

O R CH3 + H2O

+ H2OR C

O

R R CH2 R

Zn - Hg

Concentrated HCl

Zn - Hg

Concentrated HCl Slide 33

R C

H

O R CH3 + H2O

+ H2OR C

O

R R CH2 R

Zn - Hg

Concentrated HCl

Zn - Hg

Concentrated HCl

Reactions of Aldehydes and KetonesWolf-Kishner reductionR C

H

O

R C

O

R

R CH3 + H2O

R CH2 R + H2O

KOH/NaOH

NH2 NH2

KOH

NH2 NH2

Slide 34

R C

H

O

R C

O

R

R CH3 + H2O

R CH2 R + H2O

KOH/NaOH

NH2 NH2

KOH

NH2 NH2

Reactions of Aldehydes and KetonesReactive α- HydrogenThe α-Hydrogen in aldehydes and ketones is acidic in nature. Itis due to the strong electron withdrawing group.C O

Slide 35

Reactive α- HydrogenThe α-Hydrogen in aldehydes and ketones is acidic in nature. Itis due to the strong electron withdrawing group.C O

Reactions of Aldehydes and KetonesAldol condensation

CH3 C

H

O CH3 C

H

Odil NaOH

CH3 C

H

OH

CH2 C

H

O

CH3 CH CH C

H

O

But - 2 - enalaldol

3 - Hydroxy butanal

acetaldehyde acetaldehyde

CH3 C

O

CH3 CH3 C

O

CH3

Ba(OH)2CH3 C

OH

CH3

CH2 C

O

CH3CH3 C CH C

O

CH3

CH34 - Methyl pent - 3en - 2 one

Ketal(4 - Hydroxy, 4 - Methyl Pentan - 2 one)

Slide 36

CH3 C

H

O CH3 C

H

Odil NaOH

CH3 C

H

OH

CH2 C

H

O

CH3 CH CH C

H

O

But - 2 - enalaldol

3 - Hydroxy butanal

acetaldehyde acetaldehyde

CH3 C

O

CH3 CH3 C

O

CH3

Ba(OH)2CH3 C

OH

CH3

CH2 C

O

CH3CH3 C CH C

O

CH3

CH34 - Methyl pent - 3en - 2 one

Ketal(4 - Hydroxy, 4 - Methyl Pentan - 2 one)

Reactions of Aldehydes and KetonesCross aldol condensationBenzaldehyde + Acetophenone OH-/ Δ 1,3-Diphenylprop-2-enone

Slide 37C

O

H CH3 C

O

C

OH

H

CH2 C

O

-H2O

CH CH C

O

1.3 . diphenyl Propzentone

OH

Dil NaOH

Reactions of Aldehydes and KetonesElectrophilic Substiution:Aromatic aldehydes and Ketones undergo electrophillicsubstitution to give meta- substituted product

C

H

OC

H

O

NO2Metanitro benzaldehyde

Concentrated HNO3

Concentrated H2SO4

Slide 38C

H

OC

H

O

NO2Metanitro benzaldehyde

Concentrated HNO3

Concentrated H2SO4

Reactions of Aldehydes and KetonesCannizzaro’s reaction(Reactions + Aldehydes which have no α – Hydrogen

2 H C O

HKOH

50%HCOOK + CH3OH

Potassiumformate

Methanol

2C

H

O KOH50%

COOK CH2 OH

PotassiumBenzoate

BenzylacloholSlide 39

2 H C O

HKOH

50%HCOOK + CH3OH

Potassiumformate

Methanol

2C

H

O KOH50%

COOK CH2 OH

PotassiumBenzoate

Benzylaclohol

Reactions of Aldehydes and KetonesUses(i) :FormaldehydeIn the manufacture of latex rubber.Preparation of Formalin(40% solution for preserving biologicalspecimen), Trioxane , Bakelite(Thermosetting polymer) &Urotropine(urinary antiseptic)Uses(ii) : AcetaldehydeIn the preparation of acetic acid , ethyl acetate & vinyl acetate.Paraldehyde(hypnotic) and metaldehyde(solid fuel) Slide 40

Uses(i) :FormaldehydeIn the manufacture of latex rubber.Preparation of Formalin(40% solution for preserving biologicalspecimen), Trioxane , Bakelite(Thermosetting polymer) &Urotropine(urinary antiseptic)Uses(ii) : AcetaldehydeIn the preparation of acetic acid , ethyl acetate & vinyl acetate.Paraldehyde(hypnotic) and metaldehyde(solid fuel)

Reactions of Aldehydes and KetonesUses(iii) : BenzaldehydeUsed in perfumery, dye industriesUsed as flavoring agentUsed in the preparation of Cinnamic acid, Malachite greenUses (iv) : AcetoneUsed as industrial solventUsed in the preparation chloretone(hypnotic), Mesityl oxide,Phorone, Mesityline, chloroform and iodoform Slide 41

Uses(iii) : BenzaldehydeUsed in perfumery, dye industriesUsed as flavoring agentUsed in the preparation of Cinnamic acid, Malachite greenUses (iv) : AcetoneUsed as industrial solventUsed in the preparation chloretone(hypnotic), Mesityl oxide,Phorone, Mesityline, chloroform and iodoform

Reactions of Aldehydes and KetonesUses (v) :AcetophenoneUsed in the preparation of Tear gas phenacyl chlorideUsed in the preparation of a hypnotic ‘Dypnone’

Slide 42

Uses (v) :AcetophenoneUsed in the preparation of Tear gas phenacyl chlorideUsed in the preparation of a hypnotic ‘Dypnone’

1. Which is the most suitable oxidising agent used to convertprimary alcohol into an aldehyde?(a) Acidified K2Cr2O7 (b) Acidified KMnO4(c) Alkaline KMnO4 (d)

Slide 44

1. Which is the most suitable oxidising agent used to convertprimary alcohol into an aldehyde?(a) Acidified K2Cr2O7 (b) Acidified KMnO4(c) Alkaline KMnO4 (d)2. When PCC is used as an oxidising agent, which is the solventused?(a) T.H.F (b) Diethyl ether(c) (d) Carbon disulphide

PCC

Dichloromethane

3. Which is the product obtained 2–Pentene undergoesozonolysis followed by treating with Zn + H2O?(a) Acetone (b) Acetaldehyde(c) Propionaldehyde (d) Acetaldehyde and propionaldehyde

Slide 454. What is product formed, when vapours of acetic acid arepassed over heated MnO at 573K?(a) Formaldehyde (b) Acetaldehyde(c) (d) Acetic anhydrideAcetone

5. What is the product formed when propyne is treated withdilute H2SO4 in presence of HgSO4 catalyst?(a) Propene (b) Propanal(c) Propanol (d)Propanone

Slide 46

5. What is the product formed when propyne is treated withdilute H2SO4 in presence of HgSO4 catalyst?(a) Propene (b) Propanal(c) Propanol (d)6. Phenyl cyanide treated with SnCl2+ con. HCl and the productformed treated with dilute acid gives(a) Phenol (b) Benzoic acid(c) (d) Benzyl alcohol

Propanone

Benzaldehyde

In this, reactant A is(a) CO2 (c) (d) CH3OH

7. CH3 MgI + ADry Ether

BH2O

H+CH3CHO

Slide 47

In this, reactant A is(a) CO2 (c) (d) CH3OH(b) CH3 C

OCH3

7. CH3 MgI + ADry Ether

BH2O

H+CH3CHO

HCN

8. In the reactionwhich is the electrophile?(a) (b) (c) (d)

CHO

+CO + HCl +HClAnhydrous

AlCl3

Slide 48

8. In the reactionwhich is the electrophile?(a) (b) (c) (d)CO CHO Cl CHO

CHO

+CO + HCl +HClAnhydrous

AlCl3

9. A dihaloalkane on alkaline hydrolysis produces a ketone withformula C3H6O. The compound is(a) 1,2-Dichloropropane (b) 1,1-Dichloropropane(c) (d) 1,3-Dichloropropane2,2-Dichloropropane

Slide 49

9. A dihaloalkane on alkaline hydrolysis produces a ketone withformula C3H6O. The compound is(a) 1,2-Dichloropropane (b) 1,1-Dichloropropane(c) (d) 1,3-Dichloropropane10. Which one of the following is present in the blood ofdiabetic patient?(a) Methanol (b) Ethanoic acid(c) (d) Propanal

2,2-Dichloropropane

Propanone

11. 3-Pentanone and 2-Pentanone are(a) (b) Chain Isomers(c) Functional isomers (d) Optical isomersMetamers

Slide 50

11. 3-Pentanone and 2-Pentanone are(a) (b) Chain Isomers(c) Functional isomers (d) Optical isomers12. In aldol condensation the intermediate formed is(a) Carbonium ion (b) Nitrene(c) Carbene (d) Enolate ion

13.The product formed when Benzaldehyde is treated withacetaldehyde in presence of dilute NaOH is(a) Benzyl alcohol (b) Ethanol(c) Benzoic acid (d)Slide 51

13.The product formed when Benzaldehyde is treated withacetaldehyde in presence of dilute NaOH is(a) Benzyl alcohol (b) Ethanol(c) Benzoic acid (d) 3–Phenyl prop-2-enal

14.Identify A in the above reaction.(a) Acetone (b) Acetaldehyde(c) Formaldehyde (d)

CH3 MgI + A B PropaneDry

Ether

NH2 - NH2

KOH

Slide 52

14.Identify A in the above reaction.(a) Acetone (b) Acetaldehyde(c) Formaldehyde (d)

CH3 MgI + A B PropaneDry

Ether

NH2 - NH2

KOH

Ethane nitrile

15. Haloform reaction is given by the compounds having(a) CH2 – OH group (b) – COOH Group(c) – COOCH3 group (d)C

O

CH3

Slide 53

15. Haloform reaction is given by the compounds having(a) CH2 – OH group (b) – COOH Group(c) – COOCH3 group (d)C

O

CH3

16. Acetaldehyde and Benzaldehyde differ in reaction with(a) Tollen’s Reagent (b) HCN(c) NaHSO3 (d)Dilute NaOH

17. Dypnone, a hypnotic is obtained from(a) Acetone (b) Acetaldehyde(c) (d) BenzaldehydeAcetophenone

Slide 54

17. Dypnone, a hypnotic is obtained from(a) Acetone (b) Acetaldehyde(c) (d) Benzaldehyde18. Phenacyl Chloride prepared from acetophenone is used as(a) Polymer (b) Antioxidant(c) (d) Antiseptic

Acetophenone

Lachrymater

19.Which one of the following statements is wrong?(a)(b) Aldehydes and ketones are polar compounds.(c) Aldehydes are more reactive than ketones.(d) Aldehydes and ketones are reduced to alcohols.

Aldehydes and ketones are good reducing agents.

Slide 55

19.Which one of the following statements is wrong?(a)(b) Aldehydes and ketones are polar compounds.(c) Aldehydes are more reactive than ketones.(d) Aldehydes and ketones are reduced to alcohols.

Aldehydes and ketones are good reducing agents.

20.(a) (b) (c) RCOOH (d)R C C H

H2O 70 oC

H2SO4 +HgSO4

A A is

R C O

H R C CH3

O

Slide 56

20.(a) (b) (c) RCOOH (d)

21. Both formaldehyde and acetaldehyde give similar reactionswith all the reagents except(a) Schiff reagent (b) Tollen’s reagent(c) (d) Fehling solution

R C O

H R C CH3

OR CH2 OH

Ammonia

22. In the Cannizzaro’s reaction, the slowest step is(a) Attack of OH on Carboxyl group(b)(c) Removal of H+ from COOH(d) Attack of H+ on Carboxyl groupThe transfer of Hydride ion to the Carboxyl group

Slide 57

22. In the Cannizzaro’s reaction, the slowest step is(a) Attack of OH on Carboxyl group(b)(c) Removal of H+ from COOH(d) Attack of H+ on Carboxyl group23. C2H5CHO and can be distinguished using(a) Phenyl hydrazine (b) Hydroxyl amine(c) Sodium bisulphate (d)CH3 C

O

CH3

Fehling solution

24. Acetophenone is converted into Ethyl benzene by using(a) NaBH4 (b) LiAlH4(c) Sodium + Alcohol (d)Zn–Hg + Con. HCl

Slide 58

25. In Rosenmund reduction the role of BaSO4 is(a) Catalyst(b) Prometer(c) To absorb the heat evolved(d) To decrease the activity of catalyst palladium

26.Here B is(a) CH3CH2OH (b) CH3CN(c) CH3CH=N – OH (d)

CH3 C O

H

+ NH2 OH

LiAlH4A B

Slide 59

26.Here B is(a) CH3CH2OH (b) CH3CN(c) CH3CH=N – OH (d)

CH3 C O

H

+ NH2 OH

LiAlH4A B

CH3 – CH2 – NH2

27. Crossed aldol condensation is not given by(a) Acetaldehyde and Acetone(b) Acetaldehyde and Benzaldehyde(c) Propionaldehyde and Acetaldehyde(d) Slide 60

27. Crossed aldol condensation is not given by(a) Acetaldehyde and Acetone(b) Acetaldehyde and Benzaldehyde(c) Propionaldehyde and Acetaldehyde(d) Benzaldehyde and Formaldehyde

28.Here C is(a) (b)(c) (d)

CH3 C CH3

O

+ CH3 MgIEther H2O

H+A B

Copper

300 oCC

Slide 61

28.Here C is(a) (b)(c) (d)CH3 CH CH2 CH3 C

CH3

CH2

CH3 CH2 CH2 OH CH3 COOH

29. A compound gave a positive Tollen’s test. It also answeredhaloform test. The compound was(a) (b) Acetone(c) Acetophenone (d) PropanalEthanal

Slide 62

29. A compound gave a positive Tollen’s test. It also answeredhaloform test. The compound was(a) (b) Acetone(c) Acetophenone (d) Propanal30. On reduction with LiAIH4, which of the following gives anoptically active compound?(a) Propanal (b) Propanone(c) Butanol (d) Butanone

31. Which of the following has highest boiling point ?(a) Propanone (b) 2-Pentanone(c) Butanone (d) 2-Hexanone

Slide 63

31. Which of the following has highest boiling point ?(a) Propanone (b) 2-Pentanone(c) Butanone (d)32. Benzaldehyde does not react with(a) Tollen’s reagent (b)(c) 2,4-DNP solution (d) NaHSO3

2-HexanoneFehling solution

33. Which one of the following gives violet colour with neutralFerric Chloride solution?(a) Acetaldehyde (b) Benzaldehyde(c) (d) FormaldehydeSalicylaldehyde

Slide 64

33. Which one of the following gives violet colour with neutralFerric Chloride solution?(a) Acetaldehyde (b) Benzaldehyde(c) (d) Formaldehyde34. Which one of the following is used to convert Benzaldehydeinto Toluene?(a) LiAlH4 (b) NaBH4(c) Sodium and alcohol (d)

Salicylaldehyde

Zn-Hg + Con. HCl

35. A carbonyl compound reacts with hydrogen cyanide to formcyanohydrin which on hydrolysis forms a racemic mixture of α-hydroxy acids. The carbonyl compound is(a) Diethyl ketone (b) Dimethyl ketone(c) Formaldehyde (d)Slide 65

35. A carbonyl compound reacts with hydrogen cyanide to formcyanohydrin which on hydrolysis forms a racemic mixture of α-hydroxy acids. The carbonyl compound is(a) Diethyl ketone (b) Dimethyl ketone(c) Formaldehyde (d) Acetaldehyde

36. Iodoform test is not given by(a) Pentan-2-one (b) Ethanol(c) (d) EthanalPentan-3-one

Slide 66

36. Iodoform test is not given by(a) Pentan-2-one (b) Ethanol(c) (d) Ethanal37. CH3CHO and C6H5CH2CHO can be distinguished by(a) Benedict’s test (b) Tollen’s reagent test(c) (d) Fehling’s reagent test

Pentan-3-oneIodoform test

38. An aromatic compound X with molecular formula C9H10O gives2,4-DNP test, Tollen;s test, undergoes Cannizaro reaction and onvigarous oxidation gives 1,2-benzene dicarboxylic acid. X is(a) 2-Methylacetophenone (b) 3-Ethylbenzaldehyde(c) (d) 3-MethylacetophenoneSlide 67

38. An aromatic compound X with molecular formula C9H10O gives2,4-DNP test, Tollen;s test, undergoes Cannizaro reaction and onvigarous oxidation gives 1,2-benzene dicarboxylic acid. X is(a) 2-Methylacetophenone (b) 3-Ethylbenzaldehyde(c) (d) 3-Methylacetophenone2-Ethylbenzaldehyde

39. Aldol condensation between which of the following twocompounds followed by dehydration gives methyl vinyl ketone?(a)(b) Formaldehyde and acetaldehyde(c) Two molecules of acetaldehyde(d) Two molecules of acetoneFormaldehyde and acetone

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39. Aldol condensation between which of the following twocompounds followed by dehydration gives methyl vinyl ketone?(a)(b) Formaldehyde and acetaldehyde(c) Two molecules of acetaldehyde(d) Two molecules of acetone

40. Which of the following reactions will not result in the formationof carbon-carbon bonds?(a) Friedel-Craft acylation(b) Reimer- Tiemann reaction(c) Wurtz reaction(d) Slide 69

40. Which of the following reactions will not result in the formationof carbon-carbon bonds?(a) Friedel-Craft acylation(b) Reimer- Tiemann reaction(c) Wurtz reaction(d) Cannizzaro reaction

41. Trichloroacetataldehyde is subjected to Cannizzaro’s reactionby using NaOH. The mixture of the products contains sodiumtrichloroacetate and another compound. The other compound is(a) Trichloromethanol(b) 2,2,2-Trichloropropanol(c) Chloroform(d) Slide 70

41. Trichloroacetataldehyde is subjected to Cannizzaro’s reactionby using NaOH. The mixture of the products contains sodiumtrichloroacetate and another compound. The other compound is(a) Trichloromethanol(b) 2,2,2-Trichloropropanol(c) Chloroform(d) 2,2,2-Trichloroethanol

42. Consider the reaction:RCHO+NH2NH2 → RCH=N-NH2What sort of reaction is this?(a) Electrophilic addition-elimination reaction(b) Free radical addition-elimination reaction(c) Electrophilic substitution-elimination reaction(d) Slide 71

42. Consider the reaction:RCHO+NH2NH2 → RCH=N-NH2What sort of reaction is this?(a) Electrophilic addition-elimination reaction(b) Free radical addition-elimination reaction(c) Electrophilic substitution-elimination reaction(d) Nucleophilic addition-elimination reaction

43. Which of the following ketones cannot be prepared bypyrolysis of a suitable calcium salt of a fatty acid?(a) Benzophenone (b) Pentan-3-one(c) (d) Propanone

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43. Which of the following ketones cannot be prepared bypyrolysis of a suitable calcium salt of a fatty acid?(a) Benzophenone (b) Pentan-3-one(c) (d) Propanone44. Cyanohydrin of which of the following gives lactic acid onhydrolysis?(a) CH3COCH3 (b) HCHO(c) C6H5CH2CHO (d)

Butanone

CH3CHO

45. Which of the following reagents can help in separating amixture of acetone and isopropyl alcohol?(a) NaOH (b) NaCl(c) (d) NaHSO4

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45. Which of the following reagents can help in separating amixture of acetone and isopropyl alcohol?(a) NaOH (b) NaCl(c) (d) NaHSO4NaHSO3

46. Arrange the following compounds in increasing order of theirreactivity in nucleophilic addition reactions; Ethanal(I),Propanal(II), Propanone(III) and Butanone(IV).(a) III<II<I<IV (b) II<I<III<IV(c) (d) I<II<III<IV

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46. Arrange the following compounds in increasing order of theirreactivity in nucleophilic addition reactions; Ethanal(I),Propanal(II), Propanone(III) and Butanone(IV).(a) III<II<I<IV (b) II<I<III<IV(c) (d) I<II<III<IVIV<III<II<I

47. Which of the following compounds does not react with sodiumbisulphate?(a)Benzaldehyde (b)(c)Acetone (d)AcetaldehydeSlide 75

47. Which of the following compounds does not react with sodiumbisulphate?(a)Benzaldehyde (b)(c)Acetone (d)AcetaldehydeAcetophenone

48. A compound A has molecular formula C2Cl3OH. It reducesFehling’s solution and on oxidation gives a monocarboxylicacid B. A is obtained by the action of Cl2 on ethyl alcohol. A is(a) (b) Chloroform(c) Chloromethane (d) Chloroacetic acidSlide 76

48. A compound A has molecular formula C2Cl3OH. It reducesFehling’s solution and on oxidation gives a monocarboxylicacid B. A is obtained by the action of Cl2 on ethyl alcohol. A is(a) (b) Chloroform(c) Chloromethane (d) Chloroacetic acid49. Acetone on distillation with conc. H2SO4 forms(a) Phorone (b) Acrolein(c) (d) Mesityl oxide

Chloral

Mesitylene

50. Compound A C5H10O forms a phenylhydrozone and gives negativeTollen’s & iodoform test. On reduction it gives n-pentane. A is(a) Pentanal (b) Pentan-2-one(c) (d) Amyl alcohol

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50. Compound A C5H10O forms a phenylhydrozone and gives negativeTollen’s & iodoform test. On reduction it gives n-pentane. A is(a) Pentanal (b) Pentan-2-one(c) (d) Amyl alcohol51. With which of the following reagents, carbonyl compound showsaddition cum elemination reaction?(a) Carbonium ion (b)(c) HCN (d) NaHSO3

Pentan-3-oneBrady’s reagent

52. Which one of the following is crotonaldehyde?(a) CH2=CH-CHO (b) C6H5-CH=CH-CHO(c) (d) C6H5(OH)CHOCH3-CH=CH-CHO

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52. Which one of the following is crotonaldehyde?(a) CH2=CH-CHO (b) C6H5-CH=CH-CHO(c) (d) C6H5(OH)CHO53. Which of the following will give negative test with Brady’reagent?(a)CH3CHO (b)(c) CH3-CO-CH3 (d) C6H5CHOCH3-O-CH3

54. The reaction of chloroform with acetone gives(a) Mesityline (b) Ethylidene chloride(c) (d) ChloralChloretone

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54. The reaction of chloroform with acetone gives(a) Mesityline (b) Ethylidene chloride(c) (d) Chloral55. Hexamethylene tetramine is used as(a) Analgesic (b) Antipyrtic(c) Hypnotic (d) Urinary antiseptic

56. Reaction involving formation of trioxane from methanal iscalled(a) Aldol condensation(b) Condensation polymerization(c)(d) Cannizzaro’s reactionSlide 80

56. Reaction involving formation of trioxane from methanal iscalled(a) Aldol condensation(b) Condensation polymerization(c)(d) Cannizzaro’s reactionAddition polymerzation

57. What is Stephan’s reaction?(a) An alkyl isocyanide is reduced with Na/alcohol.(b) An alkyl cyanide is reduced with LiAlH4.(c) An alkanoyl chloride is reduced with Pd/BaSO4.(d)Slide 81

A57. What is Stephan’s reaction?(a) An alkyl isocyanide is reduced with Na/alcohol.(b) An alkyl cyanide is reduced with LiAlH4.(c) An alkanoyl chloride is reduced with Pd/BaSO4.(d) An alkyl cyanide is reduced with SnCl2 and HCl.

58. Schiff ’s reagent is:(a) Magenta solution decolourised with chlorine.(b) Ammonical cobalt chloride solution.(c)(d) Cannizzaro’s reactionSlide 82

58. Schiff ’s reagent is:(a) Magenta solution decolourised with chlorine.(b) Ammonical cobalt chloride solution.(c)(d) Cannizzaro’s reactionRosaniline hydrochloride decolourised with H2SO3.

59. Which of the following reactions is a condensation reaction?(a) HCHO → Paraformaldehyde(b)(c) CH3CHO → Paraldehyde(d) H2C=CH2 → PolyethyleneCH3COCH3 → Mesityl oxide

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59. Which of the following reactions is a condensation reaction?(a) HCHO → Paraformaldehyde(b)(c) CH3CHO → Paraldehyde(d) H2C=CH2 → Polyethylene

60. In the following sequence of reaction, end product isCaC2 H2O A Hg2+/H2SO4 B [O] C Ca(OH)2/ heat D(a) Acetaldehyde (b) Formaldehyde(c) Acetic acid (d)

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60. In the following sequence of reaction, end product isCaC2 H2O A Hg2+/H2SO4 B [O] C Ca(OH)2/ heat D(a) Acetaldehyde (b) Formaldehyde(c) Acetic acid (d) Acetone

Slide 85Thank You.