Problem_Set_4 - below for Y = H CH 3 Br OCH 3 NO 2 CHO and...

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Chem 3580 - Spring 2009 Problem Set #4 1. Write down the structures for A and B. Show their stereochemistry and explain the observed stereochemical outcome for each step. LiAlH 4 is a hydride (H ) source. OH S O O Cl pyridene A ONa O DMSO (solvent) B OH 1. LiAlH 4 , THF 2. H 2 O 2. When a series of alkyl acetates were treated with water in dilute acid the following reactivity order was observed: alkyl = CH 3 > CH 3 CH 2 > CH(CH 3 ) 2 > C(CH 3 ) 3 . Explain 3. Suggest a plausible mechanism to account for each of the following transformations. Use the curved arrow formalism to indicate the direction of electron flow and show electron pairs on the heteroatoms directly involved in the reaction. N O CH 3 CH 3 1. HO , H 2 O, ! OH O 2. H 3 O + (CH 3 ) 2 NH 2 4. Predict the reactivity order for the series of p -substituted methyl benzoates in the reaction shown
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Unformatted text preview: below for Y = H, CH 3 , Br, OCH 3 , NO 2 , CHO, and NH 2 . O O Y O O Y HO — H 2 O + CH 3 OH 5. When acetic acid is treated with trifluoroacetic anhydride followed by treatment with ethanol, ethyl acetate and trifluoroacetic acid are produced. Explain by mechanism each reaction and account for why ethyl trifluoroacetate and acetic acid were not formed. O CF 3 O O F 3 C O CF 3 O O OH O O OH O + + F 3 C OH O 6. Write the major organic product for each reaction. DIBAH = iBu 2 Al-H is a hydride (H — ) source. OEt O 1. EtMgBr 2. H 3 O + (a) Cl O NH 2 pyridine (b) O OH CH 3 OH HCl, ! (c) Ethyl 4-Methylvalerate 1. DIBAH 2. H 3 O + (d) OH O O O pyridine (e) NH 2 O 1. LiAlH 4 2. H 3 O + (f)...
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