IMPORTANT ORDER AND FACTS OF ORGANIC CHEMISTRY
1. RCOCl > RCOOCOR > RCOOR > RCONH2 Nucleophilic substitution reaction.
2. HI > HBr > HCl > RCOOH > C6H5OH > H2O > CH CH > NH3 (Acidic nature).
3. CCl3CHO > HCHO > CH3CHO > CH3COCH3 Nucleophilic addition reaction.
4. CH2 = CH2 > CH CH > C6H6 Electrophilic addition reaction.
Electrophilic Substitution Reaction
Nucleophilic Substitution Reaction
Nucleophilic Substitution Reaction
10. (CH3)2C = C(CH3)2 > CH3 - CH = C -(CH3)2 > CH3 - CH = CH - CH3 > CH3 - CH = CH2 (Stability)
(Heat of Hydration)
13. NI3 > NBr3 > NCl3 > NF3 (Basic strength)
14. Br2 > Cl2 > I2 (Selectivity for halogenation)
15. Halogenation of alkenes by cyclic halonium state, so anti attack takes place.
16. Hydroboration followed by oxidation is always anti markownikoff’s addition due to steric effect.
17. Oximercuration - demercuration is m.K. addition of water because some carbocation character in cyclic mercurium state.
18. CHCl3 in the presence of strong bases forms biradical : CCl2 which undergo addition with double or triple bonds.
19. When conjugated diene reacts with alkene or alkyne it is known as diel’s elder synthesis.
20. Ozonolysis of cyclo alkene forms one mole dialdehyde while ozonolysis of cyclo alkadiene forms two moles of dialdehyde.
21. Ozonolysis with (CH3)2S is known as reductive ozonolysis.
22. Hydration of alkyne occur’s in HgSO4 and dil H2SO4.
24. Cis-2-butene reacts with Br2 to forms dl() pair of enantiomers of 2,3-dibromobutane while in case of trans-2-butene forms meso-2,3-dibromo butane due to anti addition always.
25. Haloform test given by species with CH3CO-group but not in case of A.A.E. and tert. Butyl alcohol.
26. Chloral reacts with chloro benzene in con. H2SO4 to form insectiside DDT.
27. NBS is used for free radical allylation.
28. Rate for SN1 reaction is 3° > 2° > 1° in protic polar solvent.
29. Rate for SN2 reaction is 1° > 2° > 3° in polar aprotic solvent like DMSO, DMF, HMPT.
30. Chemical reactions like Hoffmann carbylamine and Reimer Tiemann’s reaction active species is biradical CCl2.
31. If cyclo 1,3-penta diene reacts with CHCl3 and potassium tert. butoxide to form chlorobenzene.
32. Alkyl halides reacts with AgCN to form isocyanides due to ambident nature of nucleophile, other ambident nucleophiles are and SO3-2.
33. In dehydration of alcohols active species is carbocation so rearrangement occurs like hydride shift or alkyl shift.
34. Dehydration of cyclobutyl methyl alcohol ring expansion takes place, formation of cyclo pentene occurs.
35. In esterification where acid reacts with alcohol to form ester, - OH given by acid while - H by alcohol
36.Ether’s reacts with HI to form alcohol and halide where fission of lower ether by SN2 mechanism while higher ethers like ter. butyl methyl ether or alkyl methyl ether by SN1 mechanism.
37. Quantitative estimation of ethers is done by ziesal’s method.
38. If unsym. cyclic ether undergo fission it depends upon medium weather it is acid or basic like in acidic medium some character of carbocation so nucleophile goes to carbon where more alkyl groups are there while reverse in basic medium due to steric factor.
39. Aldehydes are reducing agent while ketones are not.
40. Aldehydes and ketones are separated by tollen’s reagent.
41. Carbonyl and noncarbonyl are seprated by sodium bi sulphite and bradye’s reagent.
42. As the size of alkyl group increases steric hindrance comes into play, reactivity towards nucleophilic addition decreases.
43. Aldehydes with hydrogen atom in the presence of dil base undergo enolization and form carbonian to give aldol product.
44. If there is two-CHO group with hydrogen atom to form cyclic intra aldol product.
45. Aldehydes without -hydrogen atom in the presence of con. alkali to form each molecule of acid and alcohol by hydride active species.
46. Glyoxal reacts with con. KOH to form glycolate ion by Intra Cannizaro’s.
47. Pinacol pinacolone type reactions involve protonation, deprotonation and alkyl shift.
48. Aldol, Perkin, reformatsky and knovengel’s reactions are classified as carbanian active reaction.
49. In Beckmann’s rearrangement migration of group which is anti to-OH group takes place.
50. Beckmann’s rearrangent is a reaction of oximes in the presence of H2SO4 or PCl5 to produce N-alkyl amide derivatives.
51. Migratory attitude of alkyl group in Pinacol-pinacolone, beckmann’s and bayer villegar oxidation is
- C6H5 > (CH3)3C - > (CH3)2CH - > C2H5 - > CH3-
52. Cyclo hexanoneoxime on beckmann’s reaction gives caprolectum which on reaction with to give polymer nylon-6
53. 2-methyl propanal even contains -hydrogen atom but does not give aldol reaction.
54. Diphenyl glyoxal reacts with con. KOH to form salt of benzillic acid.
55. Propanone in the presence of dry HCl gas by enolic intermediate to form diacetone alcohol undergo heating form mesityl oxide. If this again reacts with propanone to form phoron.
56. Benzaldehyde reacts with alc. KCN to form Benzoin which on oxidation form benzil.
57. By wittig reaction carbonyl compounds are converted into E-Z form of alkene.
58. Benzaldehyde do not respond to benedict’s and fehling’s solution due to less redusing power of aromatic aldehyde.
59. HCOOH respond to oxidising agent due to presence of - CHO group.
60. HI > H2SO4 > HNO3 > RCOOH > H2CO3 > C6H5OH > H2O > CH CH > NH3 > CH3 - C CH > CH2 = CH2 > H2 this is decreasing acidic nature.
61. Acids with -hydrogen atom when reacts with halogen in the presence of P to form -haloacid (HVZ).
62. Carboxyllic acid on reaction with PCl5, CH2N2 and H2O to form higher acid or next homologue.
63. For reactivity of acid derivatives use funda weaker the base better the leaving group.
64. Acid amide on reaction with PCl5 to form alkane nitrile.
65. Anhydride on reaction with carbonyl compound in the presence of base (carbanian) forms ,-unsaturated carboxyllic acid (perkin reaction)
66. Amide on reaction with Br2 and alkali to form primary amine of lower homologue. Intermediate species is nitrene which undergo intra rearrangement to form RNH2.
67. Ester’s with -hydrogen atom in the presence of strong base to form carbanian undergo nucleophilic substitution reaction forms -keto ester for example ethyl acetate in the presence of pot. ter. Butoxide form aceto acetic ester (AAE). reaction is known as clesen’s ester condensation of four types
(a) Simple clesen’s ester condensation.
(b) CROSS clesen’s ester condensation.
© Intra CEC (Dieckmann’s condensation).
(d) mixed clesen ester condensation.
68. For a compound to be aromatic it must be cyclic, planar and obey (4n + 2) electron rule.
69. Cyclooctatetraene is non aromatic compound while pyrrole, pyredene, furan, cyclopentadieneylanion all are aromatic.
70. In aromatic electrophilic substitution reaction there is no hydrogen isotopic effect except sulphonation and iodination.
71. m- directing groups like nitrobenzene and benzaldehyde cannot undergo fridal craft reaction.
72. Phenol is less acidic than general carboxylic acid, cannot react with NaHCO3.
73. Anilene is more reactive than phenol towards electrophilic substitution reaction because less energy difference between nitrogen and carbon.
74. Benzene diazonium chloride reacts with phenol or anilene to form azo compounds.
75. C6H5NH2 > C6H5OH > C6H5OR > C6H5Br > C6H5NO2 (Reactivity towards electrophilic substitution reaction