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ASS5 - CHEMISTRY HTK ASSIGNMENT 5 V 1 Write equations that...

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Unformatted text preview: / CHEMISTRY HTK ASSIGNMENT 5 V 1. Write equations that describe reactions which could be used to prepare l-bromopropane from: a) propan- l —01 b) propene c) propane Remember to specify necessary reagents and reaction conditions. Write equations to show the substitution reactions of 1-bromopropane with: a) b) C) d) e) f) a) b) d) aqueous sodium hydroxide sodium methoxide ammonia potassium cyanide benzene aminomethane Which of the following compounds would react most quickly with sodium iodide in acetone? i) bromobenzene ii) bromoethane iii) 2-bromopropane iv) 2-bromo-2-butene Write the complete mechanism for the reaction you chose, identifying the substrate and the leaving group. Draw a potential energy diagram for the reaction and a 3D structure of the transition state. Which of the following reagents would react faster with l-bromobutane? i) sodium iodide / alcohol ii) sodium chloride / alcohol A compound containing Mammmmmwmmmer, but dig not mix with it. When warmed with dinhxdmxidflolmion, the liquid dissolved and the resulting mixture formed a cream to very pale yellow precipitate..mith.§ih&€1nitmle solution. Wlfll the original li_quid was boiled with althDliQmLassinmhydmxide, agas which decolourized bromine solution was evolved. Identify the substances used and explain the chemistry involved, writing equations for all reactions which occurred. b) Describe the NMR spectra expected from the organic substances used or formed during the reactions. TURN OVER Q? Propose good syntheses for the following compounds starting from 3-methy1butan—1-ol: a) 2-methyl-1-butanthiol , (CH3)2CHCH2CHZSH b) 2-methylbutane c) 3-methy1- l—butene d) 3—methylbutan—2—ol Outline syntheses of the following compounds from l—bromobutane: a) butane b) octane c) but-l-ene (D d) cis—but—Z-ene e) trans-but-Z-ene . f) l-butyne g) 3-octyne h) _2-bromobutane i) pentanenitrile j) n—butyl phenyl ether .7 Write mechanisms for all steps in part ((1) and (j). 093’» ‘ f z Some l-iodo—Z-methylheptane was mixed with sodium amide, NaNH2 in ether in order to prepare the corresponding amine, l-amino-Z—methylheptane. A good yield of a liquid c m ound with the followin IR. 5 ctrum wa ai (1, Explain this observation, by analyzing the spectrum and writing a mechanism for the reaction which occurred. I FREQUENCY (CM-ll 1800 1600 TRANSMITTANCE (x) IR PHASE liquid film NMR SOLVENT ma. «1 a 0 e w. W g .m m w. m S m 0 F: 7 m s T e, W e nNU M m. m m d m m 6 h 7k. W m m 00 d m1 3 m , mam. 0 neroo m M :7,B, w W U m m6.8. e ‘ m 6 51L. an... M R .Dln w 0 MHZ W U U C a m6.8. .n R E e P95 .10. E S T a .w , a D: S A x .H w . 5 Dn .S D c M 3 8 M A m A .. U n , ...
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