Test 3_CEB Summer 2014.pdf

5 provide the best reagents for the following

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under or next to an arrow (12 pts). 5) Provide the best reagents for the following transformations. In some cases, there may be more than one correct answer. (18 pts; 3 pts ea) O O CH 3 OH, H + OH OCH 3 O O OH O Cl O Cl O N H O OH CH 3 O O OH OH NH O OH O NH 2 CN NH 2 1. NaBH 4 2. H 3 O + 1. NH 3 2. NaBH 4 H 3 O + , Δ SOCl 2 NaOH, H 2 O PBr 3 CH 3 CH 2 NH 2 (2 equivalents) NH 3 (2 equivalents) CH 3 OH, base Mg AgNO 3 , NaOH (Tollens’) PCC H 3 O + ,Hg(OAc) 2 Br 2 , CH 3 CO 2 H 1. CH 3 MgBr 2. H 3 O + 1. LiAlH 4 2. H 3 O + or H 2 O CrO 3 H 2 SO 4 or H 3 PO 4 , Δ m CPBA NaCN Cl 2 , FeCl 3 CH 3 C(O)OC(O)CH 3 NaSH Na + SCH 2 CH 3 I 2 , H 2 O H 2 , Lindlar catalyst HI TFA (CF 3 CO 2 H) H 2 , garbage bag, Mg, a match CO 2 (dry ice)
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6) Starting from benzyl alcohol , draw a synthesis of 1-phenylpropan-2-yl acetate . You can use any reagents you wish. It might be useful to use Grignard chemistry to make a carbon-carbon bond. An acid chloride or an anhydride may helpful for installing an ester (10 pts). 7) Complete the following multi-step synthesis problem by filling in the empty boxes below. (6 points) 8) Complete the following multi-step synthesis problem by filling in the empty boxes below. (6 points) OH O O 1-phenylpropan-2-yl acetate benzyl alchohol HOCH 2 CH 2 OH H + 1. CH 3 MgBr (2 equiv) 2. H 3 O + (workup and deprotection step) OCH 3 O O O 1. CH 3 MgBr 2. H 3 O + (with loss of NH 3 ) 1. NaBH 4 2. H 3 O + O
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9) Draw the MAJOR products for the following reactions. (21 pts; 3 pts each) Sign Below: I pledge on my honor that this exam was completed by me, that I received no unauthorized help, and that I have not violated the academic conduct code of Washington State University. Please sign your name 1. LiAlH 4 2. H 3 O + O OCH 3 1. CH 3 MgBr 2. H 3 O + (workup step) O HO OH O H + (catalytic) Hint: intramolecular Fischer Esterification O O 1. NaOH 2. H 3 O + (workup step) O O NaSH Cl 1. Mg 2. 3. H 3 O + H H O 1. LiAlH 4 2. H 2 O or H 3 O + (workup step) O NH 2
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