Ch_322a_8.015

Ch_322a_8.015 - HC CH + NaNH 2 NaC CH HC CH NaNH 2 Liq NH 3...

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Synthetic Strategies involving Alkenes and Alkynes In designing a synthesis, attention must be given to: The Carbon Skeleton Functional Groups Regio- and Stereochemistry Synthetic planning begins with a retrosynthetic analysis . The product is analyzed frst and a synthetic scheme is developed by working backwards towards the starting materials and simpler compounds.
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Example of a Retrosynthesis The Synthesis of 1-Butene from Simpler Compounds CH 3 CH 2 CH=CH 2 1-butene CH 3 CH 2 C CH + H 2 CH 3 CH 2 C CH CH 3 CH 2 Br + NaC CH critical C-C bond forming step
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Unformatted text preview: HC CH + NaNH 2 NaC CH HC CH NaNH 2 Liq NH 3 , -33 o C NaC CH CH 3 CH 2 Br Liq NH 3 , -33 o C CH 3 CH 2 C CH H 2 Pd/CaCO 3 Quinoline (poisoned catalyst) CH 3 CH 2 CH=CH 2 Complete Synthesis Synthesis of cis-1,2-cyclohexanediol from Bromocyclohexane H H OH HO cis-1,2-cyclohexanediol + 2HO syn-hydroxylation H Br dehydrobromination Complete Synthesis H H H Br KOBu-t t-BuOH, heat E2 reaction occurs via axial conformation (i) OsO 4 , pyridine (ii) NaHSO 3 H H OH HO H H OH HO...
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Ch_322a_8.015 - HC CH + NaNH 2 NaC CH HC CH NaNH 2 Liq NH 3...

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