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    Chapter 6 ALDEHYDES, KETONES AND CARBOXYLIC ACIDS ALDEHYDES AND KETONES INTRODUCTION | Vanillin structure - 2 Sabeybldehyde structure - cH= CHCHO 3, Name the structure - 4, Benzophenone structure - 5, Name this structure - cHo 6, Draw 3-Oxepentanal 1 Pentane-|S-dal structure 3, Draw propane-|2,3-tricarbaldehyde 4 Valeraldehyde structure - 10. Acrolein structure CHO I Name the structure - ‘CHO 12. Isophthalaldehyde structure - 1B Terephthaldehyde structure - 1h. Mesty! oxide formule 15 Acetaldehyde formule 16. Formaldehyde formula - PREPARATION OF ALDEHYDES AND KETONES. 21. Reaction in the previous question is called - 22, DIBAL-H fl form i - 23, DIBAL-H do not attack on double bond because - oy Au 24, RON 2.H,0 25, CH, — CH=CH-CH,CH,-cN > CH, — CH=CH-CH,CH,-CHO S 6 i] 1. DIBAL-H CH,(CH,), — C— 00,4, “TG CH, ACT + cro, ? Ho, ween 28 Above reaction is called - (NEET) CH, Ml CHO ” Co + c40, + (cH,Co,0 272280, ? te, Co (NET 2018) 30. i/o, Ho, co aan ’ (NEET 2020) CHO 3 Co ———- oy (NEET 32. Above reaction is vid - 33. RMgX + CaCl2 > 34, RCOCI + R2Cd > pNMaBr . 35, CH, — CH, — C = N + C,H.MgBr—S“£"> CH,CH, — C, — ‘C,H, 36 (C6HSCH2)2Cd + 2CH3C0CI > CH, 31. 1.€r0,C1, 2.H,O* No, | PHYSICAL PROPERTIES 38. The boing points of aldehydes and kelones ore higher than hydrocarbons and ethers of comporable molecular masses. T/F 34 Compare the bp of alcohol, ether ketone, aldehyde, hydrocarbons when they have almost the some molecular mass. 40, Metharal is» gas/iquid 4 Ethanol is a gas/lqud 42. Aldehyde from H-bond with water. T/F CHEMICAL REACTIONS Nucleophilic addition & reducti 43. Ketones are generally more reactive than aldehydes in nucleophilic addtion reactions. 1/F bb \_/080,H1_ proton transfer \ c=0 + NaHso, —=c - 7 Nona 45, Keetale are gem-datkony compounds. T/F ROH OR’ 46 HCl gas, a ROH RCHO == | RCH =— OH aL AGB HCl gas R,_ /0- Ch, Cc H,O dil. HCL R% No—cu * 48 What is the function of dry HCl in the above reaction ? 44 OH Net 7 wuz =o + H.N-Z 50. Schiffs base ie - (NET) 51. Nome the reagent and product nome of each species of compounds SS ae Deonit Doone Deon Hon NH, Dean, —m) denn 6 i i ra, dears La, 52. 2.4-DNP test is for - 53. _______ colour solution is obtained if 24-DNP test is positive. Nn, 2H 5h C=0 Har? 55. Above reaction is called - (NEET) , NH.NH, ? \ 86 Somo SENS 2) Do + ee 511 Above reaction is called - (NEET) oO Ok a . oO S54 on O28 : oO 60. Date cr oO tk ae HO’ oO 62. A HO: fo} ow |__} Siiylene glyco? HO Oxidation 6h, Toles and Fehings reagent oxide aldehydes. T/F 65, What is Toller’ reagent ? 66 Tolen's test and fehlng test are used fo distinguish - 61 Tellen's test for fructose is ve. T/F 68 If the tollens test is +ve, _____ is produced (NEET) 64 Tellens and fehling fests occur in acide/akalne medum 10. Write the Toles test reackon 1 Fehling testis ove for ~ (2) 10. Febling solution A is __ 1B. Rochell salt is called Th, On heating am aldehyde with Fehling’s reagent, colour preiptate is obtained 15 Write the reaction of the Fehling test 16. Aromatic aldehyde also give fehlng test. 1/F T1 In benedics tet, instead of rochele sal ______ is used and all other things are some as feng fest oO IL B at oy, BOX i é Ln He _ and febling solution B is Naoct ae Hy CH, C7 \ 80, lodoform test is used to fest the presence of Aldol condensation & Cannizzaro 31, B-hydrony ketones are caled - group. (NEED ail. NaOH, 82. 2. CH,-CHO CH,-CH-CH,-cHO —8-> OH CH, Ba(OH), I A == CH,-C-CH,CO-CH, 83. 2CH,-CO-CH, OH 84. Reagents and conditions used in aldol condensation are - (NEET) 8 Oe) got 86. RDS (rate determining step) in cannizzoro is - 87 Reagents used in canrizaro are ~ 88. Benzallehyde + Formaldehyde + conc. NoQH —> 84. The smal/bg aldehyde unit in cannizaro is oxidised. T/F ON 40 o + NH=NH No,—> 41 Benzoldehyde are veed in - (2) 2. Acetaldehyde is used primarily as a staring material in the manufacture of - (5) CARBOXYLIC ACID INTRODUCTION 43. Common name of CH3CH2COOH - 4b. Ocalic acid iupac name ie - 95, Malonic acid formula ~ 96. Adc acid formula - 41. From ethanedioic acid 40 hexanedioic acid tell the commen name of each acid 98 Phenylacetic acid structure - 494. IUPAC name of - (i) tt (i) PhCH,CH,COOH PREPARATION OF CARBOXYLIC ACIDS 100. Primary alcohol are oxidised to carbonylic acid by - (3) (NET) 10! Jones reagent is - 02 enon + 1. alkaline KMnO, 103 co. _KMnO-KOH ha 104. CHLCHCHS x4e0-KOH cH, 105 exc __Katno-KOH A Il ford 106 RON ior On R-C_wu, Horo HO a HO 101 cH,CONH, =—os c h —<-* com, + 108 co 18, 107 RMg-X + O=c=0 Paster, A AED, BB Idenfify A&B NEED 110. Benzcic anhydride on hydrolyse give in on sep W2. RCCI3 + A > RCOOH. What is A ? IIB, R-C=C-R’ + A > RCOOH + RCOOH What is A ? Wh. CH2=CH2 + CO + H20 (H2PO4/5713K-6 13K] > IIS. The above reaction is called and it follows the markovnikov/anti-markovrikov mechanism. Il6, R-CH-COOH A COOH IN]. How to convert cyclohexene to hexane-6-dioic acid ? II8. Convert 2-Nitrobromobenzene to 3-Nitrobenzoic acid. PHYSICAL PROPERTIES I. Upto carbons carbonyl acide exist as luis. 120. Carboxyle acids have bp even higher than alcahele of comparable molecular masses, T/F 12l, The reason of the above statement is - (NEET) 122. Carboxylic acids are soluble in water upto __ carbons CHEMICAL REACTIONS 123. Carboxylic acide are less acidic than phenol, 1/F [24, Any substitution af ortho position will decreace the acide strength of benzoic acid T/F 125, Arrange the groups N02, CN, CF3, Ph, |. Br. CL.1 in increasing acidity order when they are attached to corboryc acs (NEED 126 Direct aHachment of groups such as phenyl or vinyl fo the carbonyle acid increases the acidly of corresponding carboxylic acid. T/F [21 The reason for the increase in acidity is because of resonance. T/F 128, The reason for increase in acidity is ~ 9 Q 4 \ Hea 24. HC—C, + —CH; Poa” \ OF PLO,a OH HO’ 130. Esterification is a kind of electrophilic/nucleophilic substitution 181 RCOOH + A > RCOCI + POC + HCl Identify A 132. RCOOH + PCIS —> (NEET) 183. RCOOH + SOCI2 > (NEET) [Bl Why is SOCI2 prefered while Forming acid chloride from carboxyhe acid ? 185. CH,COOH+NH, == A so; What are A & B? cOONH, DONH, © B64+8 =e (Cf +0 (NEED a 137. NaBH dees not reduce the carboxyl group. T/F 138, Carbonyl acids are reduced by - (2) 134. Diborane can easily reduce functional groups such as ester, halo,ete. T/F NaOH & CaO Heat M0. R-COONa (1) 4. R-CH,-COOH —=s-——— R-CH-COOH (NEED x 142. The above reaction is called - ‘COOH COOH ts O + cry SEAL, oO. scr cm, COOH Tek, Br,/FeBr, Sun 14S, Adipic acid when heated form - ANSWERS + ALDEHYDES AND KETONES Ho cHO on oct, on 3. Cinnamaldehyde oO i ‘CoO 5. Cycloheranecarbaldehyde 6 H,C—CH,— C— CH,— C—H 1. CHO-CH2-CH2-CH2-CHO g ONC-CH=-CH— CH= CHO CHO 4. CH3-CH2-CH2-CH2-CHO 10. CH2=CH-CHO Il Phtholaldehyde cHo. Ik, (CH3)2C=CHCOCH3 15. CH3CHO 16. HCHO CHO fl. 18, Rosenmund reduction (9. RLCH=CH2 + PaCle Chir/H20/CWCI2] > R-CO-CH3 + Pads HCI 20. RCH=NH 21 Stephen reaction 22. Diisobutylaluminiam hydride 23. H- given by DIBAL-H have high electron density which cause repulsion with double bond 24. RCHO 25.1 AIH(i-Bul2, 2 H20 7 i CH,(CH,), —C —H CH(OCrOHCL), CHO: Chromium complex 28. Elard reaction CH(OCOCH,), 4 Co CHCl, CHO oC Cr SIA-CO,HC! —B- anhyd AICI8/CuCI 32. Gattermann-Kech reaction 33. RICd + MqXCI 34, R-CO-R + Cale a CH, — C. 3 Newt, 21 36. C6445, H2-CO-CH3 37, NO, 387 34 Aleohel > Ketone >» Aldehyde > Ether > Hydrocarbon 40. Gas 4A Volatile lid 427 43.F 0S0.Na Det 7 Non 45.7 oR’ 46. R-CH + ‘OR’ H,0 WR, cHOH Rv CHLOH 48 Profonates the axygen ofthe carbony! compounds and therefore increase the electrophiiity of the carbonyl carbon \ i DC=NZ + HO 50. Substituted imine 56 Dexa, . KOH/ethylene glycol + heat 51 Wolff-Kishner reduction a a) Oo 60 ‘al 6. any 8% HO’ HO 64. 65. Ammeniacal sver ritrate eolution 66. Aldehydes from ketones all aldehydes given sve fellens and feblng test 61LF, tlle’ testis sve for fructose even when it a ketone becouse O-hydraxy ketone get oxidized by follens test the hydroxyl group get oxidised 68. Bright silver mirror 64. Alkaline SI. rr ee See R Amine Deane Substituted mine on sydraguimine | e-t-OH nme a tiytasine | CaN, tydeazne 2.4-Dinitrophenyl- * hydrazine t semlearbazide NH—C=NH, —— 52. Carbonyl group 53 Red orange colour sh SCH, + 1,0 7 55. Clemmensen reduction on dea —Q>-10, Q t Deonnnt Conn, 2.4 Dinitrophenyl- hydrazone ‘Semicarbazone TO. RCHO + 2IAgINH3I2Is + 30H. > RCOO- + Ag + H00 + NHS 1 Aliphatic aldehyde and B-hydrovy ketone 12. A Aqueous copper sulphate, B ~ Rochelle salt 1B. Alkaline sodum potassium tartrate Th. Reddish brown 15. R-CHO + Cuds + OH- > RCOO- + 16.F TI Sedium potassium citrate 9° Cu20 + H20 I 8. a aaa + CHX, Se He 4 o> + CHCl, ‘\ O° 80. CH3C0- and CH3CH(OH)- 8 Ketol 82. CH3-CH=CH-CHO CH, 83. CH,-C=CH-CO-CH, 84. dilNaOH or any base in the Ist reaction dehydration by heating in the 2nd reaction & Crore D 86 Hydride shift 87 Cone NadH/KOH 88 Benzyl alchol + Formic acid 84 Small rsar-C 90 oO 41 Perfumery ard dye industry 4. Acetic acid, ethyl acetate, vinyl acetate, polymers and dru + CARBOXYLIC ACID 48. Propionic acid tt. Ethanedioic acid 95. HOOC-CH2-COOH 96. HOOC-(CH2)4-COOH 7. Oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid (Mnemonic - OM Shanti Gao] cx,coon % Cc 49.) 2-Methyleyclopentanecarbonyle acid (i) 3-Phenylpropancic acid 100. KMnOb, K2Cr207 and Jones reagent (01 Cr03 in ache media (02 RCOOH ‘OOK 103 ow ato, cook coon (04, Co ato, Co 105. gives nothing as terfary group is rot affected 106. RCOOH (07. CH3COOH.», NHB (08. + NH, 109, R-COO-MgX+, RCOOH "0.2 CEHECOQH,., Mh COOH + GHOH Il2. AqKOH/H20 113, Hot conc. KMnO4/Hs lls. CH3-CH2-COOH IIS. Koch reaction markovnikov 116, R-CH2-COOH + COZ Kno. H,50, I teat ‘ oe se Oy a2. OPE & ven Now IN 00H 00H _60,_, ayica” °. 19.9 120.T 12\, This is due to more extensive association of carbonyl acid melecules through intermolecular H bonding 122.4 123.F 12h. F 125. Ph < |< Br

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