PS_11 - Problem Set#11 Swager 5.12 Due Friday December 2...

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1 Problem Set #11 Swager 5.12 Due Friday December 2, 4:00 PM 1. Suggest reagents and organic fragments (3 carbons or less) to carry out the following transformations. OH OH O O O O CH 2 HO CN N O O O O H N O OCH 3 O
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2 2. Fill in the boxes with the starting materials that will produce the following products. 1. TsCl, HN(CH(CH 3 ) 2 ) 2 , Heat 2. O 3 3. S(CH 3 ) 2 4. NaBH 4 HO OH 1. 2. TsCl 3. DBU Li 1. PBr 3 2. (CH 3 ) 3 COK 3. OsO 4 4. NaHSO 3 5. PCC (2 eq.) O O
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3 3. Give the products of the following reactions. Show all stereoisomers. O 1. (CH 3 ) 2 CH-Li 2, H + /H 2 O 1. PBr 3 2. Ph 3 P 3. CH 3 Li OH OH HO OH NaCr 2 O 7 (excess) H 2 SO 4 I 1. Mg, Et 2 O 2. CH 3 CHO 3. PCC 4. CH 3 CH 2 NH 2 + trace acid
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4 4. Provide detailed mechanisms for the following transformations. O O HO OH O TsOH (cat) -H 2 O OH NH 2 O OPh PhO O Cl TsOH (cat) Pyridine N O O O
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5 #4 (Cont.) O TsOH (cat) Et 2 O solvent OH O O OCH 3 Br 2 in DMF Br O + CH 3 Br
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6 #4 (Cont.) O TsOH (cat) PhOCH 3 (high boiling solvent) Heat O O O (hydrazine) H 2 N NH 2 DMF, heat, cat. H + N NH
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7 5.
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