CHEM
TEST 4_CEB Summer 2015.pdf

9 pts hoch 2 ch 2 oh h 1 ch 3 mgbr 2 equiv 2 h 3 o

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Complete the following multi-step synthesis problem by drawing products in the empty boxes below. (9 pts) 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 O NaOEt EtOH O NaOEt EtOH O Br 2 FeBr 3 CH 3 O CH 3 H Br Anisole O OH HO H N PCC CH 3 CH 2 NH 2 TFA (CF 3 CO 2 H) 1. NaBH 4 2. H 2 O (workup step)
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8) Draw a mechanism to explain the ring-opening trans-esterification on the cyclic ester (lactone) shown below. Show all intermediates and use curved arrow notation to show all bond-making and bond-breaking steps. If you need to indicate a proton transfer , just write “proton transfer” under or next to an arrow (11 pts). 9) Fill in the blanks (12 points) O O CH 3 OH, H + OH OCH 3 O O O HS Br 2 acetic acid NaSH EtOH NaOEt EtOH NaOCH 3 CH 3 OH 1. NaOCH 3 2. Br 1. NaOH, H 2 O (saponification) 2. H 3 O + , heat (decarboxylation) H 3 CO O OCH 3 O O
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10) Draw the MAJOR product(s) for the following reactions. (27 pts) 1. LiAlH 4 2. H 3 O + O OCH 3 H 2 , Pd NO 2 H 3 C OCH 3 HNO 3 H 2 SO 4 AlCl 3 Cl O 1. LiAlH 4 2. H 3 O + O OH Cl 2 , FeCl 3 OCH 3 O 2 N H 2 CrO 4 CN H 3 O + , heat 1. LiAlH 4 2. H 2 O or H 3 O + (workup step) O N H
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11) Circle all the chiral centers of the antibiotic Amoxicillin (4 pts) 12) Provide the type of hybridization for each of the atoms indicated below. (5 pts.) a) ______ b) ______ c) ______ d) ______ e) ______ 13) Draw the enolate ion of 1,3-cyclohexadione and
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