Ch_322b_12.09

Ch_322b_12.09 - Planning a Grignard Synthesis...

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Planning a Grignard Synthesis Retrosynthetic analysis is very helpful in designing an alcohol synthesis that incorporates a Grignard reaction. The alcohol product may be deconstructed in several ways. A B C The path selected often is determined by the availability of the required starting compounds. C OH R R' R'' RMgX + C O = R' R'' R'MgX + R-C-R'' O R''MgX + R-C O R'
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Examples CH 3 CH 2 CCH 2 CH 3 C 6 H 5 OH 3-phenyl-3-pentanol CH 3 CH 2 CCH 2 CH 3 C 6 H 5 OH Retrosynthetic Analysis C 6 H 5 MgBr + CH 3 CH 2 CCH 2 CH 3 O = 3-pentanone Synthesis Br bromobenzene Mg diethyl ether MgBr H 3 O + CH 3 CH 2 CCH 2 CH 3 C 6 H 5 OH workup CH 3 CH 2 CCH 2 CH 3 O diethyl ether CH 3 CH 2 CCH 2 CH 3 C 6 H 5 OMgBr
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CH 3 CH 2 -C-CH 2 CH 3 C 6 H 5 OH Retrosynthetic Analysis The identical R groups allows the ester route to be used. CH 3 CH 2 MgBr 2 + C 6 H 5 CO 2 CH 3 methyl benzoate Synthesis CH 3 CH 2 Br Mg diethyl ether CH 3 CH 2 MgBr bromoethane CH 3 CH 2 MgBr 2 + C 6 H 5 CO
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Ch_322b_12.09 - Planning a Grignard Synthesis...

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