html5-img
1 / 34

primary

primary. alcohol. excess KOH. CH 3 CH 2 CH 2 Cl. HC = CH. BrCH 2 CH 2 Br. CH 3 CH 2 CH 2 OH. PCl 5 /PCl 3 / SOCl 2 /HCl. HOCH 2 CH 2 OH. LiAlH 4 Dry ether. CH 3 CH 2 OH. Conc. H 2 SO 4. Br 2. MnO 4 - , OH -. H + , Cr 2 O 7 2- Heat, reflux. PCl 5 /PCl 3 / SOCl 2 /HCl. [O].

gabe
Télécharger la présentation

primary

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. primary

  2. alcohol excess KOH CH3CH2CH2Cl HC=CH BrCH2CH2Br CH3CH2CH2OH PCl5/PCl3/ SOCl2/HCl HOCH2CH2OH LiAlH4 Dry ether CH3CH2OH Conc. H2SO4 Br2 MnO4-, OH- H+, Cr2O72- Heat, reflux PCl5/PCl3/ SOCl2/HCl [O] CH3CH2CO2H O3/Zn, H2O CH2==CH2 CH3CHO CH3CO2H H+, H2O H2CO Br2(aq) HBr NaOH C2H5OH Alc. KOH BrCH2CH2OH CH3CH2Cl CH3CH2CN C6H5OH NaOH KCN P2O5 LiAlH4 Dry ether Excess NH3 CH3CH2OC6H5 LiAlH4 Dry ether Little NH3 CH3CH2CONH2 Br2 NaOH Alkaline hydrolysis (CH3CH2)3N CH3CH2CH2NH2 CH3CH2NH2 Excess NH3 CH3CH2COO- LiAlH4 Dry ether CH3CH2CH2Cl CH3C==N ALKYL HALIDE AS USEFUL INTERMEDIATE

  3. Benzene Reaction Chart C6H5CH2CH3 Sulphonic acid C6H5SO3H Zn/Hg c. HCl C6H5COCH3 Conc. H2SO4 1,3-dinitrobenzene C6H5CO2H Benzoic acid CH3COCl/AlCl3 Conc. H2SO4/HNO3 60oC MnO4- /H+ CH3Cl/AlCl3 C6H6 Nitrobenzene C6H5CH3 Methylbenzene conc. H2SO4/HNO3 • Sn, conc. HCl • NaOH Cl2, light Br2/FeBr3 C6H5CH2Cl (ChloroMethyl)benzene Aniline HNO2, 0oC Alkaline Naphthal-2-enol C6H5Br Bromobenzene CuBr Aryl diazonium ion, C6H5-N=N+ H2O Azo Dye (coupling) Phenol H3PO2 CuCN CyanoBenzene Benzene

  4. C-acylation HOC6H4COCH3 C6H5OCH3 4-hydroxyBenzenesulphonic acid CH3COCl/AlCl3 CH3Br Conc. H2SO4 O-acylation C6H5O- Na+ C6H5OCOCH3 2-bromophenol or 4-bromophenol NaOH CH3COCl Or CH3CO2H Br2/FeBr3 C6H5OH CH3Cl/AlCl3 Br2(aq) 2,4,6-tribromophenol 4-methylphenol Or 2-methylphenol Dil. HNO3 Na Ar-N=N+ 4-nitrophenol Or 2-nitrophenol Sodium phenoxide C6H5O- Na+ + H2 Coupling reaction Phenol Reaction Chart

  5. CH2==C(CO2H)CH3 Conc. H2SO4 (CH3)2C==C(CH3)2 CH3CH(OH)CH3 O3,, Zn/H2O Ozonolysis CH3C(OH)(CO2H)CH3 H+, H2O Dil. HCl CH3C==N(CH3) CH3 CH3C(OH)(SO3-)CH3 CH3CH==CH2 CH3C(OH)(CN)CH3 H2O KCN, Alcohol Conc. H2SO4 Conc. H2SO4 NaHSO3(aq) NaBH4 or LiAlH4 ether CH3C(OH) CH3 NH(CH3) CH3COCH3 CH3CH(OH)CH3 CH3NH2 HONH2 H2N-NH2 methanol CH3C==N-OH CH3 I2, NaOH 2,4 DNP (CH3)2C==N-NH2 Propanone hydrazone CH3C==N-NH-C6H3(NO2)2 CH3 CH3CO2- + CHI3 CH3Br CH3CO2CH3 LiAlH4 ether LiAlH4 ether CH3CH2OH + CH3OH CH3CH2OH Propanone Reaction Chart

  6. CH3CH==CH(CO2H) CH3CH2COCl Conc. H2SO4 CH3CH(OH)CH3 CH3CH2CH(OH)(CO2H) H2, Pd CH3CH2CH==N(CH3) H+, H2O Dil. HCl CH3CH2CH(OH)(SO3-) CH3CH==CH2 CH3CH2CH(OH)(CN) Conc. H2SO4 H2O KCN, Alcohol Conc. H2SO4 NaHSO3(aq) NaBH4 or LiAlH4 ether CH3CH2CH(OH) NH(CH3) CH3CH2CHO CH3CH2CH2OH CH3NH2 HONH2 O3,, Zn/H2O Cr2O72-/H+ H2N-NH2 CH3CH2CH=CHCH2CH3 CH3CH2CH==N-OH 2,4 DNP Tollens’ reagent CH3CH2CH=N-NH2 Propanal hydrazone CH3CH2CO2H CH3CH2C==N-NH-C6H3(NO2)2 LiAlH4 ether CH3OH Conc. H2SO4 CH3CH2CO2-+ Ag CH3CH2CO2CH3 CH3CH2OH Tollens’ reagent Ag(NH3)2+ Propanal Reaction Chart

  7. + CHI3 C6H5O- Zn/Hg Conc. HCl CH3CO2H pyridine RNH2 I2, OH- + Ag OH- H+/Cr2O72- NH3 CH3CO2- Pd H2 CH3COCl CH3CO2H H+ heat Ag(NH3)2+ C6H6 AlCl3 CH3OH P2O5 HO- CH3CO2- + CH3OH SOCl2/PCl5 CH3CO2 CH3 H2O CH3COO-NH4+ Conc. H2SO4 CH3OH Conc. H2SO4 NH3 CH3CO2H LiAlH4 ether NH3 C6H5O- H2O heat LiAlH4 + CH3OH + CH3OH ACID DERIVATIVES REACTION CHART

  8. CH3CONH2 CH3CO2C6H5 CH3CO2COCH3 HCO2- CHI3 C6H5O- CH3CONHR Zn/Hg Conc. HCl CH3CO2H pyridine CH3 CO2H CH3CH2NH2 RNH2 I2, OH- CH3CO2- + Ag OH- H+/Cr2O72- NH3 CH3CO2- CH3CONH2 Pd H2 CH3COCl CH3CO2H H+ CH3CHO heat Ag(NH3)2+ C6H6 AlCl3 CH3OH P2O5 HO- CH3CO2- + CH3OH CH3C=N CH3COC6H5 SOCl2/PCl5 CH3CO2 CH3 H2O CH3COO-NH4+ Conc. H2SO4 CH3OH Conc. H2SO4 NH3 CH3CO2H LiAlH4 ether NH3 C6H5O- H2O heat LiAlH4 CH3CONH2 + CH3OH CH3CO2C6H5 CH3CH2OH + CH3OH CH3CO2COCH3 CH3CH2 OH ACID DERIVATIVES REACTION CHART

  9. 4-Hydroxybenzoic acid Draw the structural formula for Dettol and the other two compounds. Give the reagents and conditions for the 4-step synthesis of phenol from benzene. Write the steps for the synthesis of ethoxybenzene from phenol. 2,2-dimethylpropan-1-ol reacts with conc. HCl via SN2 pathway. Give the mechanism of the reaction. Give the E2 mechanism for the dehydrohalogenation of 2-chloro-2,3-dimethylbutane using alcoholic KOH. Why is a tertiary alcohol not used for synthesizing tertiary chloride? Why?

  10. 1 2 3 DD D 4 DD DD 5 DD DD DD 6 DD DD

  11. 7 （2） 8 9 (1) Outline a mechanism of the reaction: (2) Draw the structures of all possible stereoisomers of the product. 10 11

  12. A 12 A Is A optically active? Explain. 13 A A 14 Br2 NaOH 15 L M ethanol Give the reagents required for the four-step synthesis of phenacetin, an analgesic. 16 17 Zn/Hg c.HCl 18 Write the equation for the use of H2SO4 in making soapless detergent. 19

  13. Suggest a chemical test to distinguish one compound from the other in each pair. Each test should include the reagent(s), the expected observation with each compound. 20 A B Suggest steps for the following synthesis: 21 • C6H5CH3 3-nitrobenzoic acid Nitrobenzene  chlorobenzene 22 Toluene when treated with iron and bromine gives 4-bromotoluene as one of the products. Outline a reasonable mechanism for the reaction. 23 Arrange these iodides in order of reactivity toward hydrolysis in aqueous acid C6H5-C(CH3)2-I, C6H11-CH(CH3)I and C6H11-C(CH3)2I. 88II7b 24 Give the mechanism for the reaction of 2-methylpropene and iodine chloride(I-Cl). 25 2-bromobutane reacts with an alcoholic solution of KCN to give an optically active product. Suggest the reaction mechanism. 26 27 Outline a mechanism of the electrophilic addition: Draw the structures of all possible stereoisomers of the product. Would the product rotate a beam of plane-polarized light? Explain your answer. 00I5a4%

  14. 1 Outline a synthetic route, in not more than four steps, to accomplish these conversions. In each step, give the reagent(s), conditions and the structure of the organic product. 2 3 Outline the synthesis: 4

  15. 5 Give the reagent(s) and intermediates for these conversions: 6 7 99II7b

  16. 1 2 J J G F 3 J L K J reacts with KOH in ethanol to form P, Q. Give these structures. (2)

  17. Arrange the following compounds in the order of increasing basic strength. Explain your answer. 4 Write down the structural formula for both the intermediate and the product. 5 With experimental details, explain how you would convert cyclohexanol to cyclohexene. 6 7

  18. 1. Give the reaction mechanism for the reaction between 2-pentanone and 2,4-dintriophenylhydrazine Give the structure of the intermediates: 2. A. B. C. 3. In the preparation of propanal from propan-1-ol, a side product N (C6H12O2) was formed. (1) Suggest how N is formed. (2) Suggest one method to separate propanal from a mixture of propanal and N. 4. Suggest a possible structure for J, K and L and explain briefly your deductions. J, C5H12O, which exists as a pair of enantiomers, and reacts with phosphorus(V) chloride to give hydrogen chloride. K, C6H10, on ozonolysis gives L, C6H10O2 91II9b 5. Outline chemical tests which would allow you to distinguish between the compounds in the following pairs. Describe what you would observe in each case. 2-methylcyclohexanone and cyclohexylethanone 91II9a 2-methylpentan-2-ol and 2-methylpentan-1-ol 4 marks 6.

  19. 7 Give the reagent(s) for each step and the structures of all intermediate compounds. A B C D 8 An incomplete reaction of an amine with ethanoic anhydride gave a liquid mixture on cooling. Briefly outline a procedure, using a separating funnel and appropriate reagent(s), to isolate the ethanoylation product. 92I5b3% 9

  20. 10 • In an experiment, 25 g of (CH3)3COH react with 36 g of HCl to give 28 g of (CH3)3CCl. • Find the limiting reagent of the reaction, showing clearly your calculation. • Calculate the % yield of (CH3)3CCl. 96II7b6% • (3) Name the reaction type and outline the reaction mechanism. (use curly arrows to show movement of electron pairs) 11 6 12 7 Give the reagent(s) and brief experimental conditions for these conversions: (1) CH3CH-O-CHCH3 CH3CH=CH2 CH3 CH3 (2) nitrobenzene  chlorobenzene (3) toluene  benzaldehyde (4) butanoic acid  CH3(CH2)2NH2 74II5a 14% 13 14 14

  21. Give the reagent(s) for each step and the structures of all intermediate compounds. • C6H11-COCH3 C6H11-CH2OH • B. C6H5CONH2 3-nitrobenzoic acid • Aniline  colored dye (given reagent is: naphthalen-2-ol) • Cyclohexene  1,6-hexanedioic acid 15 16 17

  22. 18 19 20 20 • 21 The reaction of 2,3-dimethylbutan-2-ol with concentrated sulphuric acid gives 2 alkenes. • A. Suggest possible structures for the two alkenes. 05II6b 5% • B. Suggest how the 2 alkenes can be distinguished from each other by chemical means. Give the structure of the major product: 22 A. B. D C

  23. 23 24 Each conversion can be completed in not more than 3 steps. Give the reagent(s), conditions, and structure of the intermediate(s). D. A. E. B. F. C. 25

  24. CH3O-readily removes HBr Pure substitution product LiAlH4 Dry ether CN- ethanol Dilute acid

  25. 2-bromo-2-methylpentane propene CH3COCl AlCl3 LiALH4 Dry ether KCN ethanol 3-nitrobenzoic acid MnO4- H+ 4-ethylpropylbenzene

  26. trans-2-phenyl-2-butene 2-butanol loses its optcial activity in acidic medium. Explain briefly.

  27. Dehydration or SN1 occurs in acidic medium

  28. This reaction is slow as the nucleophile is sterically hindered

More Related