organic chemistry midterm 1 108B+W2015+Ex1EC+synth+key
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EC) Given an unlimited Aldrich Chemical Gold Card, start from the reagent shown and devise a synthesis of the given products that Aldrich can't afford to keep in stock. You may use any organic compounds containing 6 CARBONS or LESS and any inorganic reagents. You do not need to show a mechanism. You DO need to show each essential intermediate product and the synthesis of any organometallic reagents used. 8 --KEY--Chemistry 108B Exam #1-Winter 2015 --KEY-- (b) (a) the precursor of styrene polymer plastics (must be synthesized WITHOUT having to separate o,p or polyalkylated products) Styrene Ibuprofen To cure your O-Chem headache CH 3 O OH CO 2 CH 3 MgBr Mg CH 3 Br O HBr O polar addition of HBr H (+) OH MgBr O Br Mg O Br 2 FeBr 3 (sep o,p) O O Cl , AlCl 3 NaBH 4 OH PBr 3 9 7 Br KOH OH PBr 3 O Br MgBr Br 2 FeBr 3 Mg O O Cl , AlCl 3 O H 2 /Pd NBS Br KOH NaBH 4 OH H (+) EXTRACREDIT!!EXTRACREDIT!!HOLYCRAPEVENONEXAM1HE'SGIVINGUSEXTRACREDIT!
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Transcript of organic chemistry midterm 1 108B+W2015+Ex1EC+synth+key
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EC) Given an unlimited Aldrich Chemical Gold Card, start from the reagent shown and devise a synthesis of the given products that Aldrich can't afford to keep in stock. You may use any organic compounds containing 6 CARBONS or LESS and any inorganic reagents. You do not need to show a mechanism. You DO need to show each essential intermediate product and the synthesis of any organometallic reagents used.
8--KEY--Chemistry 108B Exam #1-Winter 2015--KEY--
(b)
(a)
the precursor of styrene polymer plastics(must be synthesized WITHOUT having to separate o,p or polyalkylated products)
Styrene
IbuprofenTo cure your
O-Chem headache
CH3
OOH
CO2
CH3
MgBr
Mg
CH3
Br
O
HBrO
polar additionof HBr
H(+)OH
MgBr
O
Br
MgO
Br2FeBr3
(sep o,p)
O
O
Cl , AlCl3
NaBH4
OH
PBr3
9
7
Br
KOHOH
PBr3
O
Br
MgBr
Br2FeBr3
MgO
O
Cl , AlCl3
O
H2/PdNBS Br KOH
NaBH4 OH
H(+)
EXTRACREDIT!!EXTRACREDIT!!HOLYCRAPEVENONEXAM1HE'SGIVINGUSEXTRACREDIT!
