Aldehydes,Ketones and. Dr.GSN 1
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1 Topics Aldehydes,Ketones and Haloalkanes Dr.GSN 1
2 Aldehydes and Ketones Aldehydes R=H, alkyl, aryl group group Ketones R&R'=alkyl /aryl Aldehydes and ketones are called carbonyl compounds.
3 Structure of Carbonyl Group Carbonyl group contains one sigma and one pi bond. Both carbon and oxygen atoms are in sp 2 hybridised d state. t Dr.GSN 3
4 Naming of aldehydes and ketones According to IUPAC: Aldehydes are named by replacing e of the corresponding alkane by suffix al. Ketones are named by replacing e of the alkane by suffix one. Aldehyde group is always at terminal hence position is normally not mentioned. In ketones we use position of carbonyl group whenever it is needed. Dr.GSN 4
5 Nomenclature R CH 2 CH 3 R CH CHO CHO R-CO-R Alkane Alkanal Alkanone CH 3 -CH 2 -CH 3 CH 3 -CH 2 -CHO CH 3 -CO-CH 3 Propane Propanal Propanone Dr.GSN 5
6 Preparation of Aldehydes and Ketones By oxidation of alcohols:- Using acidified K 2 Cr 2 O 7 Pi Primary alcohols l oxidises to aldehydes d Secondary alcohols oxidises to ketones RCH 2 OH + [O] Aldehyde + H 2 O RCHOHR' + [O] Ketone + H 2 O Dr.GSN 6
7 By Oppenauer Oxidation Secondary alcohols on refluxing with excess of acetone in the presence of aluminium tertiary butoxide forms ketones. RCHOHR' + CH 3 COCH 3 RCOR' + CH 3 CHOHCH 3 Ketone Dr.GSN 7
8 From calcium salts of fatty acids (Pyrolysis) Aldehydes are obtained by dry distilling calcium salts of fatty acids with calcium formate. Ketones are obtained by dry distillation of fatty acids other than calcium formate. Dr.GSN 8
9 Calcium salts Calcium formate Calcium formate + Calcium acetate Calcium formate + Calcium benzoate Calcium acetate Aldehyde / Ketone HCHO (fromaldehyde) CH 3 CHO (Acetaldehyde) C 6 H 5 CHO (Benzaldehyde) CH 3 COCH 3 (Acetone) Calcium benzoate C 6 H 5 COC 6 H 5 (Benzophenone) Calcium acetate + C 6 H 5 COCH 3 Calcium benzoate (Acetophenone) Dr.GSN 9
10 By Rosenmund ss Reduction Acid chlorides are reduced to aldehydes by reducing with hydrogen in the presence of palladium supported over BaSO 4. RCOCl + H c RCHO + HCl Dr.GSN 10
11 By Friedel Craft s reaction Acetophenone is obtained by this method. heat C 6 H 6 +CH 3 COCl Anhy.AlCl 3 C 6 H 5 COCH 3 + HCl Dr.GSN 11
12 By Etard s reaction When toluene is oxidised with chromyl chloride in CCl 4, benzaldehyde is formed. Even CrO 3 brings about this reaction. C 6 H 5 CH 3 +[O] CrO 2 Cl 2 / CCl 4 C C 6 H 5 CHO +H 2 O Toluene Benzaldehyde Dr.GSN 12
13 Properties of Aldehydes and Ketones 1. Lower members are soluble in water and higher members are insoluble. The solubility decreases with increase in size of alkyl groups. 2. Aldehydes and ketones have higher boiling points than the alkanes due to presence of polar carbonyl groups. However they have lower boiling points than the corresponding alkanes due to absence of hydrogen bonding. Dr.GSN 13
14 Chemical properties Addition reactions: Aldehydes and ketones undergo addition reactions with HCl, NaHSO 3 to form corresponding cynohydrines and bisulphites respectively. Dr.GSN 14
15 Condensation reactions Aldehydes and ketones undergo a number of condensation reactions with following reagents. 1. Hydroxyl amine (NH 2 OH) Oximes 2. Hydrazine (NH 2.NH 2 ) Hydrazones 3. Phenylhydrazine (NH 2 NHC 6 H 5 ) Phenyl hydrazones 4. Semicarbozide (NH 2 NHCONH 2 ) Semi carbazones 5. 2,4, dinitrophenylhydrazine (Borsche s reagent) Orange yellow crystalline compound Dr.GSN 15
16 With Grignard s reagent Formaldehyde + Grignard Reagent Addition compound Hydrolysis Primary alcohols Other aldehydes form secondary alcohols Dr.GSN 16
17 Oxidation of aldehydes Reducing property of aldehydes: Tollen s reagent + RCHO heat RCOOH +Ag Fehling s solution + RCHO heat Cu 2 O (red ppt) Benedict solution + RCHO heat Cu 2 O (red ppt) Dr.GSN 17
18 Oxidation of ketones Ketones are difficult to oxidise. Hence, they do not reduce Tollen s reagent, Fehling s solution and Benedict s reagent. But strong oxidising agents like acidified KMnO 4 and K 2 Cr 2 O 7 oxidises to carboxylic acids with less number of carbon atoms. In unsymmetrical ketones the keto group stays with the smaller alkyl group (Popoff s rule). Dr.GSN 18
19 Reduction of aldehydes and ketones 1. Aldehydes on reduction with Zn and dil. HCl, LiAlH 4 give primary alcohols. Ketones give secondary alcohols. 2. Clemmensen s reduction:- When Aldehydes and Ketones are reduced with Zn Hg/conc. HCl, hydrocarbons are formed. Dr.GSN 19
20 Special reactions Cannizzaro s reaction:- 1. Aldehydes which do not contain α hydrogen when treated with conc. NaOH undergo oxidation and reduction to give alcohol and sodium carboxylate 2C 6H 5CHO + NaOH C 6 H 5 CH 2 OH + C 6 H 5 COONa Dr.GSN 20
21 2. Aldol Condensation:- Aldehydes and ketones having α hydrogen undergo self condensation in the presence of dil. NaOH forming β hydroxy aldehydes or ketones Dr.GSN 21
22 3. Perkin s condensation:- Benzaldehyde on heating with acetic anhydride in the presence of fused sodium acetate at c gives cinnamic acid (unsaturated) C 6 H 5 CH=CHCOOH 4. Claisen condensation:- Benzaldehyde reacts with acetaldehyde in the presence of dil. NaOH to form cinnamaldehyde. C 6 H 5 CH=CH-CHO Dr.GSN 22
23 5. Benzoin condensation:- Benzaldehyde reacts with alcoholic KCN to form Benzoin. C 6 H 5 CH.OH.COC 6 H 5 Dr.GSN 23
24 Iodoform reaction:- Aldehydes and ketones having CH3CO group react with Iodine and NaOH to form yellow crystalline ppt of iodoform. (E.g., acetaldehyde and acetone) Schiff s reagent test:- t Aldehydes give immediate pink colour but ketones do not. Dr.GSN 24
25 Q1. The carbon atom of the carbonyl group is 1) sp 2 hybridised d 2) sp 3 hybridised 3) sp hybridised 4) dsp 2 hybridised Answer: (1) sp 2 hybridised Dr.GSN 25
26 Q2. Ketones can be prepared by 1) Clemmensen s s reduction 2) Rosenmund s reduction 3) Oppenauer s oxidation 4) Cannizzaro s reaction Answer (3) Oppenauer s oxidation Dr.GSN 26
27 Q3. Aldehydes are the first oxidation product of 1) Secondary alcohols 2) Primary alcohols 3) Tertiary alcohols 4) Dihydric alcohols Answer (2) Primary alcohols Dr.GSN 27
28 Q4. Ketones are the first oxidation products of 1) Primary alcohols 2) Secondary alcohols 3) Dihydric alcohols 4) Tertiary alcohols Answer (2) Secondary alcohols Dr.GSN 28
29 Q5. Which of the following will not be formed when calcium acetate is distilled with calcium benzoate 1) Acetone 2) Benzophenone 3) Acetophenone 4) Acetaldehyde Answer (3) Acetophenone is formed Dr.GSN 29
30 Q6. On heating calcium acetate and calcium formate, the major product formed is 1) CH 3 COCH 3 2) CH 3 CHO 3) HCHO + CaCOCO 3 4) CH 3 CHO + CaCO 3 Answer (4) CH 3 CHO + CaCO 3 is formed Dr.GSN 30
31 Q7. Aldehydes and Ketones do not give addition reaction with 1) HCl 2) NaHSO 3 3) HCN 4) HCl aq Answer (4) HCl aqueous Dr.GSN 31
32 Q8. Aldehydes may be distinguished from ketones by the useof 1) Conc. H 2 SO 4 2) Tollen s reagent 3) Pyrogallol 4) Grignard reagent Answer (2) Tollen s reagent (aldehydes d reduces it to Ag) Dr.GSN 32
33 Q9. Which of the following does not undergo Cannizzaro s reaction on heating with an alkali solution? 1) CCl 3 CHO 2) (CH.. 3 ) 3 C CH O 3) HCHO 4) C 6 H 5. CHO Answer (1) CCl 3 CHO (because it will cleave in presence of base) CCl 3 CHO + NaOH CHCl 3 + HCOONa 3 3 Dr.GSN 33
34 Q10. Aldol condensation will not occur in 1) HCHO 2) CH 3 CH 2 CHO 3) CH 3 COCH 3 4) CH 3 CHO Answer (1) HCHO (because it does not contain α Hatom) Dr.GSN 34
35 Q11. In which of the following reactions, aromatic aldehyde d is treated t with acid anhydride in the presence of corresponding salt of the acid to give unsaturated t aromatic acid 1) Friedel Crafts reaction 2) Perkin s reaction 3) Wurtz reaction 4) Kolbe s reaction Answer (2) Perkin s reaction C 6 H 5 CHO+(CH 3 CO) 2 O C 6 H 5 CH=CHCOOH+ CH 3 COOH Dr.GSN 35
36 Q12. Aldehydes and ketones can be reduced d to corresponding hydrocarbons by 1) Refluxing with strong acids 2) Passing the vapours over heated lead oxide 3) Refluxing with zinc amalgam and conc. HCl 4) Refluxing it with strong alkali Answer (3) Refluxing with zinc amalgam and conc. HCl (Clemmensen s reduction) Dr.GSN 36
37 Q13. The IUPAC name of is 1) 3 methyl 3 formyl 2 propane 2) 2 methyl 3 oxobutanal 3) 2 acetylpropanal 4) 3 methylbutan 3 one 1 al 3 al Answer (2) 2 methyl 3 oxobutanal Dr.GSN 37
38 Q14. Identify the compound X and Y in the following reactions. 1) Benzoic acid and Calcium acetate 2) Benzaldehyde and Calcium formate 3) Benzoic acid and Sodium formate 4) Benzaldehyde and Sodium acetate Answer (2) Dr.GSN 38
39 Q15. Decreasing order of reactivity towards nucleophilic addition reactions for the following compound I) HCHO II) CH 3 COCH 3 III) CH 3 CHO IV) C 6 H 5 COCH 3 is 1) I > III >II > IV 2) I >III > IV >II 3) III > I >II> IV 4) II >IV >III >I Answer (1) I > III >II > IV Steric hinderance to carbonyl group and +I effect of substituents decreases the reactivity HCHO>CH 3 CHO>CH 3 COCH 3 > C 6 H 5 COCH 3 Dr.GSN 39
40 Q16. Benzaldehyde can be prepared by the action of chromyl chloride on toluene dissolved in CS 2, the reaction is known as 1) Etard s reaction 2) Hoffmann s reaction 3) Schotten Baumann reaction 4) Fittig s reaction Answer (1) Etard s reaction C 6H 5CH 3 + [O] CrO 2 Cl 2 /CCl 4 C 6H 5CHO + H 2O Dr.GSN 40
41 Q17. The end product in the reaction 1) Acetaldehyde oxime 2) Formaldehyde oxime 3) Methyl nitrate 4) Acetoneoxime Answer (4) Acetoneoxime A=(CH 3 COO) 2 Ca, B=CH 3 COCH 3, C=Acetoneoxime Dr.GSN 41
42 Q.18 Acetone and acetaldehyde are 1) Functional isomers 2) Position isomers 3) Chain isomers 4) Not isomers Answer (4) Not isomers CH 3 COCH 3 &CH 3 CHO do not have same molecular formula
43 Q19. Benzaldehyde is different from aliphatic aldehydes in its reaction towards 1) Fehling s solution 2) Schiff s reagent 3) Tollen s reagent 4) NaHSO 3 solution Answer (1) Fehling s solution (because benzaldehyde undergo Cannizzaro s reaction due to presence of NaOH) Dr.GSN 43
44 Q20. If formaldehyde d and KOH are heated, we get 1) Ethyl formate 2) Acetylene 3) Methane 4) Methyl alcohol Answer (4) Methyl alcohol 2HCHO + KOH HCOOK + CH 3 OH Dr.GSN 44
45 Haloalkanes (R-X) Alkanes -H Haloalkanes C n H 2n+2 +X C n H 2n+1. X Monohalogen derivatives of alkanes are called haloalkanes (alkyl halides) Dr.GSN 45
46 Classification Based upon the type of carbon atom to which halogen atom is attached CH 3 CH 3 CH 3 -*CH 2 -Cl CH 3 -CH-Cl CH 3 -C-Cl CH 3 Chloro ethane 2-chloropropane 2-chloro-2-methyl propane Pi Primary (1 0 ) Secondary(2 0 ) Tertiary(3 0 ) Dr.GSN 46
47 Nomenclature of Haloalkanes CH 3 Cl Chloromethane CH 3 CH 2 Br Bromoethane Methods of preparation: 1. From alcohols: a. Action with halogen acid b. Action with phosphorus halides c. Action with thionyl chloride Dr.GSN 47
48 Anly HX ZnCl 2 R-X +H 2 O R-OH- PX 3 R-X +H 3 PO 3 SOCl 2 R-X + SO 2 + HX pyridine (Darzen s Process) Dr.GSN 48
49 2. From alkenes: R-CH=CH 2 + HX R-CH-CH 3 X 2 0 Dr.GSN 49
50 Dr.GSN 50
51 Differences between S N 1 and S N 2 reactions S N 1 Reactions It is a two step reaction Rate of the reaction depends upon only the concentration of haloalkanes It follows first order kinetics S N 2 Reaction It is a single step reaction Rate of the reaction depends upon the concentration of haloalkanes and nucleophile It follows second order kinetics The order of reactivity is The order of reactivity is 3 0 >2 0 >1 0 >CH 3 CH 3 >1 0 >2 0 >3 0 Reaction is favoured by polar solvents Reaction takes place with weak bases Reaction is favoured by non polar solvents Reaction requires strong bases Racemic mixture is obtained as the product The product has inversion of configuration Dr.GSN 51
52 Q21. Which of the following alkyl halides is unreactive in an S N 2 reaction? 1) Primary 2) Secondary 3) Tertiary 4) Methyl chloride Answer (3) Tertiary alkyl halides react by S N 1 reaction (not S N 2) Dr.GSN 52
53 Q22. On reaction with alcoholic KOH, 1 chlorobutane gives 1) 1 Butene 2) 2 Butene 3) 1 Butanol 4) 2 Butanol Answer (1) 1 Butene (dehydrohalogenation) ClCH 2 CH 2 CH 2 CH 3 KOH CH 2 =CHCH 2 CH 3 Dr.GSN 53
54 Q23. Which of the following compounds will produce an isocyanide on treatment with alkyl halide? 1) NaCN 2) KCN 3) AgCN 4) HCN Answer (3) AgCN RX + AgCN RNC + AgX Dr.GSN 54
55 Q24. S N 1 reaction of alkyl halide leads to 1) Retention of configuration 2) Racemisation 3) Inversion of configuration 4) None of these Answer (2) Racemisation Dr.GSN 55
56 Q25. Alkyl halides react with magnesium in dry ether to form 1) MgX 2 2) Grignard s reagent 3) Alkene 4) Alkyne Answer (2) Grignard s reagent RX + Mg dry ether RMgX Dr.GSN 56
57 Q26. Which of the following haloalkane is most reactive? 1) 1 Bromopropane 2) 1 Chloropropane 3) 2 Bromopropane 4) 2 Chloropropane Answer (3) 2 Bromopropane The order of reactivity for alkyl group is 3 0,2 0,1 0 and for halogen I > Br > Cl Dr.GSN 57
58 Q27. Which of the following statements about benzyl chloride is incorrect? 1) It is a lachrymatory liquid and answers Beilstein s i testt 2) It gives a white precipitate with alcoholic li silver nitrate t 3) It is less reactive than alkyl halides 4) It can be oxidised to benzaldehyde by boiling with cupric nitrate solution Answer (3), but benzyl chloride is more reactive than alkyl halides due to resonance Dr.GSN 58
59 Q28. On heating a mixture of two alkyl halides with sodium metal in dry ether, 2 methyl propane was obtained. The alkyl halides are 1) Chloromethane and chloroethane 2) Chloromethane and 1 chloropropane 3) 2-Chloropropane and chloromethane 4) 2-Chloropropane and chloroethane Answer (3) (CH 3 ) 2 CHCl+2Na+ClCH ClCH 3 (CH 3 ) 2 CHCH 3 +2NaCl Dr.GSN 59
60 Q29. The order of reactivities of methyl halides in the formation of Grignard s reagent is 1) CH 3 Br > CH 3 I>CH 3 Cl 2) CH 3 Br > CH 3 Cl > CH 3 I 3) CH 3 Cl > CH 3 Br > CH 3 I 4) CH 3 I>CH 3 Br > CH 3 Cl Answer (4), the order of reactivity is for the formation of Grignard s reagent is CH 3 I > CH 3 Br > CH 3 Cl Dr.GSN 60
61 Q30. The name of the product obtained by the addition of HI to propene in the presence of peroxide catalyst is 1) 1-Iodopropane 2) 2-Iodopropane 3) 1-Iodopropene p 4) Propyl iodide Answer (2), CH 3 CH=CH 2 +HI peroxide (CH 3 ) 2 CHI It is Markownikov s addition. HI does not undergo anti Markownikov s addition. Dr.GSN 61
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