R C R R=CH 3,C 2 H 5 , C 6. etc... H O R= H, CH 3, C 2 H 5, C 6 H 5, etc Ketones are compounds having general formula
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2 Aldehydes & Ketones Aldehydes are compounds having general formula H R C R= H, CH 3, C 2 H 5, C 6 H 5, etc Ketones are compounds having general formula R C R R=CH 3,C 2 H 5, C 6 H 5 etc... Slide 2
3 IUPAC names of Aldehydes Formula Common Name IUPAC Name HCH Fomaldehyde Methanal CH 3 CH Acetaldehyde Ethanal CH 3 CH 2 CH Propionaldehyde Propanal CH 3 CH 2 CH2CH Butyraldehyde Butanal (CH 3 ) 2 CHCH Isobutyraldehyde 2-Methylpropanal Slide 3
4 IUPAC names of Aldehydes Formula Common Name IUPAC Name CH 2 =CH-CH Acrolein Prop 2 enal CH 3 CH=CH-CH Crotonaldehyde But-2-enal C 6 H 5 CH=CH-CH Cinnamaldehyde 3-Phenylprop-2-enal C 6 H 5 CH Benzaldehyde Benzaldehyde C 6 H 4 (H)CH Salicyaldehyde 2-Hydroxybenzaldehyde Slide 4
5 IUPAC Names of Ketones Formula Common Name IUPAC Name CH 3 CCH 3 Acetone Propanone CH 3 CCH 2 CH 3 Ethyl methyl ketone Butanone CH 3 CH 2 CCH 2 CH 3 Diethyl ketone Pentan-3-one CH 3 CCH 2 CH 2 CH 3 Methyl propyl ketone Pentan-2-one C 6 H 5 CCH 3 C 6 H 5 CC 6 H 5 Methyl phenyl ketone or Acetophenone Diphenyl ketone or Benzophenone 1-phenylethanone Benzophenone Slide 5
6 Structure of Carbonyl group C 120 o C o Sp hybridised The carbon- oxygen double bond is polarized due to higher electro negativity of oxygen than carbon. C Hence C Electrophile Nucleophile Slide 6
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8 From oxidation of primary and secondary alcohols H R C H H PCC [] R H C H H H R C +H 2 R-CH(H)-R KMn4/KH R-C-R + H 2 Slide 8
9 By dehydrogenation of alcohols H R C H H Copper 300 o C H R C + H 2 R-CH(H)-R Cu/573K R-C-R + H 2 Slide 9
10 From alkene by ozonolysis R CH CH R CH CH 2 Zn H 2 H R C + CH 2 Slide 10
11 From Acyl Chloride By Rosenmund reduction R C H 2 Cl R C H + HCl Pd - BaS o C Slide 11
12 From Nitrile by Stephen s Reduction R C N SnCl 2 R CH NH +HCl H 2 H R C + NH 3 H + Slide 12
13 Preparation of Benzaldehyde from Toluene Etard's Reaction CH 3 Cr2 Cl 2 CH +H2 CS 2 Slide 13
14 By Gattermann Koch reaction. C 6 H 6 + C + HCl Anh AlCl3/CuCl C 6 H 5 CH Slide 14
15 Dry distillation of calium salts give aldehyde and ketones. Calcium formate Calcium formate and calcium acetate Calcium formate and calcium benzoate Calcium acetate Calcium benzoate Calcium benzoate and calcium acetate Formaldehyde - Acetaldehyde - Benzaldehyde - Acetone - Benzophenone Slide 15 - Acetophenone
16 From nitrile and Grignard reagent Dry R C N R - Mg + x R C Ether R' N. Mgx 2 H 2 R C + NH 3 H + R' + Mg X H R-MgX + HCN dry ether R-CH=NMgX H2/H+ R-CH Slide 16
17 Ketones from Acyl chloride and dialkylcadmium 2 R' C Cl + R 2 Cd 2 R' C R + CdCl 2 Slide 17
18 Aromatic ketones from Benzene by Friedel Craft reaction R C Cl Anhydrous AlCl 3 C R + HCl Slide 18
19 Physical properties of Aldehydes and ketones Physical state: HCH Gas, Up to C 13 are liquids and higher ones are solids. dour : Lower aldehydes have unpleasant odour where as higher ones have pleasant odour. Boiling points: These compounds have higher boiling points than ethers and hydrocarbons due to dipole interactions but lower boiling points than that of alcohols due to the absence of intermolecular hydrogen bonding. Slide 19
20 Reactions of Aldehydes and Ketones (i) Nucleophillic addition Nu Nu a b C Planar + Nu slow a C b Tetrahedral intermediate fast H + a C H b Addition Product Slide 20
21 Reactions of Aldehydes and Ketones With HCN Both aldehydes and ketones react with HCN to form addition product Cynohydrin (in presence of a base) HCN + H - CN - + H 2 C CN C CN H + C H CN Tetrahedral Intermediate Cyanohydrin Slide 21
22 Reactions of Aldehydes and Ketones With NaHS 3 C + Na + S - 3 H C Na S 3 H Proton Transfer C H S 3 Na Bisulphite addition Compound All aldehydes react with NaHS 3 to form a white crystalline solid, bisulphite addition compound. Many ketones also react. But acetophenone does not react with NaHS 3 due to stearic hindrance. Slide 22
23 Reactions of Aldehydes and Ketones With alcohols nly aldehydes react with alcohols in presence of dry HCl to form acetals. R H C 2 R' H dry HCl R H C R' R' +H 2 acetal Slide 23
24 Reactions of Aldehydes and Ketones With alcohols Ketones react only with Ethylene Glycol to form cyclic product R R C H 2 C C H 2 H H dry HCl R CH 2 C R CH 2 +H 2 Ethylene Glycol Ketal Slide 24
25 Reactions of Aldehydes and Ketones With ammonia derivatives NH 2 Z Where Z=H, NH 2, C 6 H 5 NH, NHCNH 2 alkyl, aryl C H 2 N Z C H NH Z C N Z +H 2 Slide 25
26 Reactions of Aldehydes and Ketones NH2-NH2 CH3CH=N-NH2 Hydrozone NH2-H CH3CH=N-H xime NH2-NHC6H5 CH3CH=N-NHC6H5 Phenyl hydrozone NH2NHCNH2 CH3CH=N-NHCNH2 Semicarbazone Slide 26
27 Reactions of Aldehydes and Ketones Mechanism - C : NH 2 Z C Z N H H H C N Z C N Z +H 2 H H + Transfer H C N - Z H Unstable Slide 27
28 Reactions of Aldehydes and Ketones xidation: Aldehydes readily get oxidized to give Carboxyacids H R C [] R CH Na Cr + H S Slide 28
29 Reactions of Aldehydes and Ketones With Tollen s reagent R H C + 2[Ag(NH 3 ) 2 ] H - RC + 2 Ag + 2H 2 + 4NH 3 Silver Mirror Slide 29
30 Reactions of Aldehydes and Ketones With Fehling solution H R C + 2Cu 2+ +5H RC + Cu 2 +3H 2 Red ppt Slide 30
31 Reactions of Aldehydes and Ketones xidation of Ketones: In presence of strong oxidising agents at high temperature ketones get oxidized. Their oxidation involves C-C bond cleavage. A mixture of Carboxylic acids having lesser number of carbon atoms formed. Ex: C H 3 C CH 3 alkaline KMn4 4[] CH 3 CH + C 2 + H 2 Slide 31
32 Reactions of Aldehydes and Ketones Reduction: Aldehydes and Ketones are reduced to primary and secondary alcohol by using LiAlH 4 /NaBH 4 H R C LiAlH 4 R CH 2 H THF Primary Alcohol R C R LiAlH 4 THF R H C R H Secondary Alcohol Slide 32
33 Reactions of Aldehydes and Ketones Reduction to Hydrocarbons (Clemmensen reduction) H Zn - Hg R C R CH 3 + H 2 Concentrated HCl R C Zn - Hg R R CH 2 R Concentrated HCl + H 2 Slide 33
34 Reactions of Aldehydes and Ketones Wolf-Kishner reduction H H 2 N NH 2 R C R CH 3 + H 2 KH/NaH R C R H 2 N NH 2 KH R CH 2 R + H 2 Slide 34
35 Reactions of Aldehydes and Ketones Reactive α- Hydrogen The α-hydrogen in aldehydes and ketones is acidic in nature. It is due to the strong electron withdrawing C group. Slide 35
36 Reactions of Aldehydes and Ketones Aldol condensation H H 3 C C acetaldehyde C H 3 C CH 3 H H 3 C C acetaldehyde C H 3 C dil NaH C H 3 CH 3 H 3 C Ba(H) 2 H C H CH 2 aldol 3 - Hydroxy butanal H C CH 3 CH 2 Ketal (4 - Hydroxy, 4 - Methyl Pentan - 2 one) H C C CH 3 H H 3 C CH CH C But enal H 3 C C CH C CH 3 CH Methyl pent - 3en - 2 one Slide 36
37 Reactions of Aldehydes and Ketones Cross aldol condensation Benzaldehyde + Acetophenone H-/ Δ 1,3-Diphenylprop-2-enone C H C H 3 C H H C CH 2 C -H 2 CH CH C Dil NaH H 1.3. diphenyl Propzentone Slide 37
38 Reactions of Aldehydes and Ketones Electrophilic Substiution: Aromatic aldehydes and Ketones undergo electrophillic substitution to give meta- substituted product H C Concentrated HN 3 Concentrated H 2 S 4 H C N 2 Metanitro benzaldehyde Slide 38
39 Reactions of Aldehydes and Ketones Cannizzaro s reaction (Reactions + Aldehydes which have no α Hydrogen 2 H H C KH 50% HCK + CH 3 H Potassium Methanol formate H 2 C KH 50% CK CH 2 H Potassium Benzoate Benzylaclohol Slide 39
40 Reactions of Aldehydes and Ketones Uses(i) :Formaldehyde In the manufacture of latex rubber. Preparation of Formalin(40% solution for preserving biological specimen), Trioxane, Bakelite(Thermosetting polymer) & Urotropine(urinary antiseptic) Uses(ii) : Acetaldehyde In the preparation of acetic acid, ethyl acetate & vinyl acetate. Paraldehyde(hypnotic) and metaldehyde(solid fuel) Slide 40
41 Reactions of Aldehydes and Ketones Uses(iii) : Benzaldehyde Used in perfumery, dye industries Used as flavoring agent Used in the preparation of Cinnamic acid, Malachite green Uses (iv) : Acetone Used as industrial solvent Used in the preparation chloretone(hypnotic), Mesityl oxide, Phorone, Mesityline, chloroform and iodoform Slide 41
42 Reactions of Aldehydes and Ketones Uses (v) :Acetophenone Used in the preparation of Tear gas phenacyl chloride Used in the preparation of a hypnotic Dypnone Slide 42
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44 1. Which is the most suitable oxidising agent used to convert primary alcohol into an aldehyde? (a) Acidified K 2 Cr 2 7 (b) Acidified KMn 4 (c) Alkaline KMn 4 (d) PCC 2. When PCC is used as an oxidising agent, which is the solvent used? (a) T.H.F (c) Dichloromethane (b) Diethyl ether (d) Carbon disulphide Slide 44
45 3. Which is the product obtained 2 Pentene undergoes ozonolysis followed by treating with Zn + H 2? (a) Acetone (b) Acetaldehyde (c) Propionaldehyde (d) Acetaldehyde and propionaldehyde 4. What is product formed, when vapours of acetic acid are passed over heated Mn at 573K? (a) Formaldehyde (c) Acetone (b) Acetaldehyde (d) Acetic anhydride Slide 45
46 5. What is the product formed when propyne is treated with dilute H 2 S 4 in presence of HgS 4 catalyst? (a) Propene (b) Propanal (c) Propanol (d)propanone 6. Phenyl cyanide treated with SnCl 2 + con. HCl and the product formed treated with dilute acid gives (a) Phenol (c) Benzaldehyde (b) Benzoic acid (d) Benzyl alcohol Slide 46
47 Dry Ether 7. CH3 MgI + A In this, reactant A is B H 2 H + CH 3 CH (a) C (b) H 3 C C CH 3 2 (c) HCN (d) CH 3 H Slide 47
48 8. In the reaction +C + HCl Anhydrous CH +HCl AlCl 3 which is the electrophile? (a) (b) (c) (d) C CH Cl CH Slide 48
49 9. A dihaloalkane on alkaline hydrolysis produces a ketone with formula C3H6. The compound is (a) 1,2-Dichloropropane (b) 1,1-Dichloropropane (c) 2,2-Dichloropropane (d) 1,3-Dichloropropane 10. Which one of the following is present in the blood of diabetic patient? (a) Methanol (c) Propanone (b) Ethanoic acid (d) Propanal Slide 49
50 11. 3-Pentanone and 2-Pentanone are (a) Metamers (b) Chain Isomers (c) Functional isomers (d) ptical isomers 12. In aldol condensation the intermediate formed is (a) Carbonium ion (c) Carbene (b) Nitrene (d) Enolate ion Slide 50
51 13.The product formed when Benzaldehyde is treated with acetaldehyde in presence of dilute NaH is (a) Benzyl alcohol (b) Ethanol (c) Benzoic acid (d) 3 Phenyl prop-2-enal Slide 51
52 14. Dry NH 2 - NH 2 CH 3 MgI + A B Propane Ether KH Identify A in the above reaction. (a) Acetone (b) Acetaldehyde (c) Formaldehyde (d) Ethane nitrile Slide 52
53 15. Haloform reaction is given by the compounds having (a) CH 2 H group (c) CCH 3 group (b) CH Group (d) C CH Acetaldehyde and Benzaldehyde differ in reaction with (a) Tollen s Reagent (c) NaHS 3 (b) HCN (d)dilute NaH Slide 53
54 17. Dypnone, a hypnotic is obtained from (a) Acetone (b) Acetaldehyde (c) Acetophenone (d) Benzaldehyde 18. Phenacyl Chloride prepared from acetophenone is used as (a) Polymer (c) Lachrymater (b) Antioxidant (d) Antiseptic Slide 54
55 19.Which one of the following statements is wrong? (a) Aldehydes and ketones are good reducing agents. (b) Aldehydes and ketones are polar compounds. (c) Aldehydes are more reactive than ketones. (d) Aldehydes and ketones are reduced to alcohols. Slide 55
56 20. R C C H H 2 70 o C A A is H 2 S 4 +HgS 4 H R C CH 3 (a) (b) (c) RCH (d) R C R CH 2 H 21. Both formaldehyde and acetaldehyde give similar reactions with all the reagents except (a) Schiff reagent (c) Ammonia (b) Tollen s reagent (d) Fehling solution Slide 56
57 22. In the Cannizzaro s reaction, the slowest step is (a) Attack of H on Carboxyl group (b) The transfer of Hydride ion to the Carboxyl group (c) Removal of H + from CH (d) Attack of H + on Carboxyl group H 23. C 2 H 5 CH and 3 C C CH 3 can be distinguished using (a) Phenyl hydrazine (b) Hydroxyl amine (c) Sodium bisulphate (d) Fehling solution Slide 57
58 24. Acetophenone is converted into Ethyl benzene by using (a) NaBH 4 (b) LiAlH 4 (c) Sodium + Alcohol (d)zn Hg + Con. HCl 25. In Rosenmund reduction the role of BaS 4 is (a) Catalyst (b) Prometer (c) To absorb the heat evolved (d) To decrease the activity of catalyst palladium Slide 58
59 26. H H 3 C C + N H 2 H A LiAlH 4 B Here B is (a) CH 3 CH 2 H (c) CH 3 CH=N H (b) CH 3 CN (d) CH 3 CH 2 NH 2 Slide 59
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 Slide 60
61 28. H 3 C C CH 3 + CH 3 MgI Ether A H 2 H + B Copper 300 o C C Here C is (a) (b) H 3 C CH CH 2 C H 3 CH 3 C CH2 (c) (d) H 3 C CH 2 CH 2 H CH 3 CH Slide 61
62 29. A compound gave a positive Tollen s test. It also answered haloform test. The compound was (a) Ethanal (b) Acetone (c) Acetophenone (d) Propanal 30. n reduction with LiAIH 4, which of the following gives an optically active compound? (a) Propanal (c) Butanol (b) Propanone (d) Butanone Slide 62
63 31. Which of the following has highest boiling point? (a) Propanone (b) 2-Pentanone (c) Butanone (d) 2-Hexanone 32. Benzaldehyde does not react with (a) Tollen s reagent (b) Fehling solution (c) 2,4-DNP solution (d) NaHS 3 Slide 63
64 33. Which one of the following gives violet colour with neutral Ferric Chloride solution? (a) Acetaldehyde (c) Salicylaldehyde (b) Benzaldehyde (d) Formaldehyde 34. Which one of the following is used to convert Benzaldehyde into Toluene? (a) LiAlH 4 (b) NaBH 4 (c) Sodium and alcohol (d) Zn-Hg + Con. HCl Slide 64
65 35. A carbonyl compound reacts with hydrogen cyanide to form cyanohydrin 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 Slide 65
66 36. Iodoform test is not given by (a) Pentan-2-one (c) Pentan-3-one (b) Ethanol (d) Ethanal 37. CH 3 CH and C 6 H 5 CH 2 CH can be distinguished by (a) Benedict s test (c) Iodoform test (b) Tollen s reagent test (d) Fehling s reagent test Slide 66
67 38. An aromatic compound X with molecular formula C 9 H 10 gives 2,4-DNP test, Tollen;s test, undergoes Cannizaro reaction and on vigarous oxidation gives 1,2-benzene dicarboxylic acid. X is (a) 2-Methylacetophenone (b) 3-Ethylbenzaldehyde (c) 2-Ethylbenzaldehyde (d) 3-Methylacetophenone Slide 67
68 39. Aldol condensation between which of the following two compounds followed by dehydration gives methyl vinyl ketone? (a) Formaldehyde and acetone (b) Formaldehyde and acetaldehyde (c) Two molecules of acetaldehyde (d) Two molecules of acetone Slide 68
69 40. Which of the following reactions will not result in the formation of carbon-carbon bonds? (a) Friedel-Craft acylation (b) Reimer- Tiemann reaction (c) Wurtz reaction (d) Cannizzaro reaction Slide 69
70 41. Trichloroacetataldehyde is subjected to Cannizzaro s reaction by using NaH. The mixture of the products contains sodium trichloroacetate and another compound. The other compound is (a) Trichloromethanol (b) 2,2,2-Trichloropropanol (c) Chloroform (d) 2,2,2-Trichloroethanol Slide 70
71 42. Consider the reaction: RCH+NH 2 NH 2 RCH=N-NH 2 What 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 Slide 71
72 43. Which of the following ketones cannot be prepared by pyrolysis of a suitable calcium salt of a fatty acid? (a) Benzophenone (b) Pentan-3-one (c) Butanone (d) Propanone 44. Cyanohydrin of which of the following gives lactic acid on hydrolysis? (a) CH 3 CCH 3 (c) C 6 H 5 CH 2 CH (b) HCH (d) CH 3 CH Slide 72
73 45. Which of the following reagents can help in separating a mixture of acetone and isopropyl alcohol? (a) NaH (b) NaCl (c) NaHS 3 (d) NaHS 4 Slide 73
74 46. Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions; Ethanal(I), Propanal(II), Propanone(III) and Butanone(IV). (a) III<II<I<IV (c) IV<III<II<I (b) II<I<III<IV (d) I<II<III<IV Slide 74
75 47. Which of the following compounds does not react with sodium bisulphate? (a)benzaldehyde (b) Acetophenone (c)acetone (d)acetaldehyde Slide 75
76 48. A compound A has molecular formula C 2 Cl 3 H. It reduces Fehling s solution and on oxidation gives a monocarboxylic acid B. A is obtained by the action of Cl 2 on ethyl alcohol. A is (a) Chloral (b) Chloroform (c) Chloromethane (d) Chloroacetic acid 49. Acetone on distillation with conc. H 2 S 4 forms (a) Phorone (c) Mesitylene (b) Acrolein (d) Mesityl oxide Slide 76
77 50. Compound A C 5 H 10 forms a phenylhydrozone and gives negative Tollen s & iodoform test. n reduction it gives n-pentane. A is (a) Pentanal (b) Pentan-2-one (c) Pentan-3-one (d) Amyl alcohol 51. With which of the following reagents, carbonyl compound shows addition cum elemination reaction? (a) Carbonium ion (b) Brady s reagent (c) HCN (d) NaHS 3 Slide 77
78 52. Which one of the following is crotonaldehyde? (a) CH 2 =CH-CH (b) C 6 H 5 -CH=CH-CH (c) CH 3 -CH=CH-CH (d) C 6 H 5 (H)CH 53. Which of the following will give negative test with Brady reagent? (a)ch 3 CH (c) CH 3 -C-CH 3 (b) CH 3 --CH 3 (d) C 6 H 5 CH Slide 78
79 54. The reaction of chloroform with acetone gives (a) Mesityline (b) Ethylidene chloride (c) Chloretone (d) Chloral 55. Hexamethylene tetramine is used as (a) Analgesic (c) Hypnotic (b) Antipyrtic (d) Urinary antiseptic Slide 79
80 56. Reaction involving formation of trioxane from methanal is called (a) Aldol condensation (b) Condensation polymerization (c) Addition polymerzation (d) Cannizzaro s reaction Slide 80
81 57. What is Stephan s reaction? (a) An alkyl isocyanide is reduced with Na/alcohol. (b) An alkyl cyanide is reduced with LiAlH 4. (c) An alkanoyl chloride is reduced with Pd/BaS 4. A (d) An alkyl cyanide is reduced with SnCl 2 and HCl. Slide 81
82 58. Schiff s reagent is: (a) Magenta solution decolourised with chlorine. (b) Ammonical cobalt chloride solution. (c) Rosaniline hydrochloride decolourised with H 2 S 3. (d) Cannizzaro s reaction Slide 82
83 59. Which of the following reactions is a condensation reaction? (a) HCH Paraformaldehyde (b) CH 3 CCH 3 Mesityl oxide (c) CH 3 CH Paraldehyde (d) H 2 C=CH 2 Polyethylene Slide 83
84 60. In the following sequence of reaction, end product is CaC H2 2 A Hg2+/H2S4 B [] C Ca(H)2/ heat D (a) Acetaldehyde (b) Formaldehyde (c) Acetic acid (d) Acetone Slide 84
85 Thank You. Slide 85
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