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Tutorial 5 answers - reagents necessary i How would you...

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Chemistry 2OA3 Nov. 23, 2010 Tutorial 5 1. Suggest a synthesis of the beta blocker propranolol using the starting materials provided. In any reaction where a stereocentre is created, indicate whether the process is stereoselective or random. Other REAGENTS may be used as long as they don’t contribute CARBONS to the synthesis. OH Br O Br NH OH Propanolol ANSWER: OH Br O Br NH OH Propanolol i) NaH ii) Br O O mCBPA O NaNH 2 Dil H 3 O + O NH 2 OH Br Both enantiomers formed The addition of the amide is stereospecific anti (back side attack) 1) 2) 2. How would you prepare the two isomers shown? ? OMe OH ? OH MeO ANSWER: ? OMe OH ? OH MeO mCBPA O MeOH MeOH/NaOMe H 2 SO 4 3. How would you convert compound W into compounds X and Z , respectively (it will take more than one step – give all reagents).
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ANSWER: O OH O O O Br O O W X Z Y cold dilute MeO- PBr 3 O OMs cold dilute MeO- U MsCl NEt 3 ? ? 4. You may use propene as your only carbon containing starting material and any other
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Unformatted text preview: reagents necessary. i) How would you make compound A? ii) How would you make alcohol D ? (You will need to use compound A) iii) Propene is converted into an alcohol E (C 3 H 8 O). The 13 C NMR shows only 2 different kinds of carbon for alcohol E . What is the structure of E ? iv) Using E and A as starting materials (and a strong base), synthesize a product C . C is an isomer of F ( C 6 H 14 O 2 ). The 1 H NMR, 13 C NMR, and IR spectra are provided for compound F . ANSWER: OH ONa O H3O+ NaH mCPBA A B i) A II) dilute H3O+ O OH HBr Br MgBr Mg, ether i) A II) dilute H3O+ OH C 6 H 14 O 2 O OH Spectra shown for this isomer C D F E SPECTRA FOR COMPOUND F 13 C NMR (5 peaks) 1 H NMR 2H 2H 2H 1H 1H 6H IR...
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