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A general Grignard procedure is presented for the synthesis of aliphatic, tertiary alcohols containing six to nine carbons. Without revealing the specific starting materials, students are challenged to identify their unknown products from physical (boiling points, refractive indices) and spectral (infrared O-H, C-H and fingerprint regions) data. Once a product is identified retro-synthetic considerations point to which alkyl halide and ketone were required as starting materials. This laboratory exercise in organic synthesis incorporates anhydrous techniques, distillation, and infrared analysis.
RX + Mg ---> [RMgX] + R'R"C=O ---> [RR'R"COMgX] ---> RR'R"COH
Criteria
RX = C2-C5 1' alkyl bromide (unbranched)
R'R"C=O = C3-C5 ketone
RR'R"COH = C6-C9 3' alcohol
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