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ASS6 - “,3 M Li d Q ‘ E 5‘ CL ” C J(0 t c CHEMISTRY...

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Unformatted text preview: “,3 M Li d, Q. ‘ E; 5‘ CL ” C J (0 t, c CHEMISTRY HTK ASSIGNMENT 6 V OH CH L CHZCHZ CH3 1. Suggest syntheses for l-butanol from the following reagents, writing mechanisms for all steps in parts a, b and e: l-butene O l-bromobutane _ / \ c) ethylene oxide and ethyl bromide (limiter/u omh 2 CH2 _ C“ a d cthene propan- l-ol f) 2-butanol 2. Write equations for the reaction of 2-pentanol with the following reagents, showing mechanisms for all Ste 3 in arts b, c, d and e: - ' P P 045 (Hi 011C142 CH3 a warm CrO3 / H2804 OH b) concentrated aqueous hydrobromic acid 9* concentrated sulphuric acid at 160°C 6)) thionyl chloride with a little pyridine @ phosphorus triiodide t) metallic potassium V 3. Write equations to show how the following substances can be prepared from the specified reagents: a) cyclopentyl n-propyl ether from cyclopentanol and l-propanol b) n-butyl phenyl ether from phenol and l-butanol c) 2—methoxydecane from l-decene and methanol (1) ether from ethanol e) 2,3-epoxyoctane from 2-octene and bromine t) cyclohexene oxide from cyclohexene 4. Write equations for the following reactions specifying the conditions if necessary and writing a mechanism for part a: Q1) sec-butyl isopropyl ether with hot concentrated hydroiodic acid solution b) tert—butyl ethyl ether with hydrobromic acid solution c) ethoxybenzene with hydroiodic acid solution ’fl) d1)" d) 2-methyl-2, 3-epoxybutane with ethanol in acid +0 do ae) l-pentene oxide with ammonia to do at) oxirane with hydroiodic acid v TURN OVER -2- / 5. Describe simple chemical tests that can be used to distinguish between the following pairs of substances. Use a different test for each pair. h) dry @ an ether and an alkane b) an ether and an alkyl halide 1m do 0) an ether and an alkene d) an ether and a primary alcohol e) an ether and an alkyne f) a primary, secondary and tertiary alcohol 6. Determine the structures of A, B, C, D and E in the following scheme and write mechanisms for the formation of A, B and C. Br2 / H20 cold CH/3—-CH=CH2-———-—-—-> -———-—-—->® 25 °C OH*(aq) 1 03 / cc14, -78°C /\ 11+ /H,_O 2. H202 / H+,A Mn04“ / OH’ (aq) 25°C . CH\3ONa / CH3OH “V Oddohua 25°C \ / 25°C cum! 5‘!“ E and F . age Wtqlump l, 7. Propose suitable syntheses for the following substances from the reagents suggested: l0 (10 a) 3- methylpentan—Z-ol from 3-methylpent-2-ene b) isopropyl alcohol from: i) an alkene ii) a haloalkane iii) from methanol via a Grignard reagent 0) l-methylcyclopentanol from 2-methylcyclopentanol d) 2-methylcyclopentanol from l-methylcyclopentanol e) butan-Z- 01 from ethanol via a Grignard reagent f) l-ethylcycylohexanol from cyclohexanone and any Grignard reagent 01501: (H; 8. Outline a method to convert propene into each of the following substances, specifying necessary reagents and reaction conditions. a) l-propanol f) propylene oxide b) 2-propanol 4 g) butan—2-one c) l,2-propanediol h) isobutyl alcohol d) propanal ‘ i) 3-methylbutan-2-ol V e) acetone j) l-butyne ENT 0‘3 I C l liduid Mm ' Identify the compound which gave the following spectra: M U {R SPECTQ ECTRUM D 1 I'MR S l ’54:? SOLV (a) (lo) ( c) JlflllLilluj 21!. 1.11 Li..r.|11.vlt ”61.1!TL.|L1.|1 . LHH AA M qtl'll. MASS SPECTRU .63: 50 7O 50 13 mle NOTES UV DATA ed .‘V c-r ion obse 'eCui ”I nom An- '.I . ‘\ (.64 3.. 1.7... .03 above no )‘max ctrum pe (TESS S in the lad. I in 020 :sen misc pp q I ninr peck ct 3. n] “l? S p. 525, Nos.: 11.33; 11.34; 11.35; 11.36; 11.37; 11.38; 11.39; 11.40; 11;42; 11.43 Solomons and Fryhle, 7'h ed. Additional Problems: ...
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