By Laurie S. Starkey
This booklet will reveal the best way to synthesize aim molecules (TMs) that
contain a number of useful teams (FGs), comparable to C≡C (alkyne), OH (alcohol
or carboxylic acid), and C=O (aldehyde, ketone, and lots of others). The process
of making plans a synthesis, referred to as a retrosynthesis, is without doubt one of the most crucial tools
within the “toolbox” had to resolve synthesis difficulties. the strategy of retrosynthetic
analysis is brought during this bankruptcy and is used all through the
book. this primary bankruptcy also will evaluation using protecting teams (PGs) in
organic synthesis. the second one bankruptcy offers extra valuable instruments needed
by the start synthesis scholar through reviewing universal nucleophiles and
electrophiles, in addition to a few normal reagents for oxidation and reduction
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Additional info for Introduction to Strategies for Organic Synthesis
Treatment of an alkene with ozone creates an ozonide intermediate that breaks down upon workup. A “reductive” workup uses a reducing agent, such as zinc or dimethylsulfide (DMS, CH3SCH3). If there were any hydrogens attached to the original C=C double bond, they are preserved in a reductive workup, and aldehyde products would be formed. The use of NaBH4 in the workup reduces the carbonyls formed in situ, affording alcohol products. If an “oxidative” workup were used instead, the added oxidizing agent (H2O2) would replace any aldehyde C–H bonds with C–O bonds to give carboxylic acid products.
Common Electrophiles Electrophile (E+) Name Example of Product with Nu: C carbocation δ+ δR X alkyl halide R-Nu O δδ+ epoxide Nu δ+ δO ketone or aldehyde δ+ Cannot put carbocation in a bottle! Instead, E+ reagents typically have δ+ sites. C Nu X = Cl, Br, I OH Nu OH Nu "1,2-addition" O of Nu: "1,4-addition" of Nu: δ+ δ+ α,β-unsat'd ket/ald (enone) OH 1,2-add'n Nu: = LiAlH4, RMgX, RLi O Nu: = enolate, cuprate, N, O 1,4-add'n (Michael) Nu δ+ O C O carbon dioxide (CO2) O Nu OH O R δ+ OR ester Nu O R δ+ Cl carboxylic acid derivatives generally add two equiv.
O3; 2. H2O2 ozonolysis with reductive workup or dihydroxylation/oxidation gives aldehyde(s) R' R OH O O R R' ozonolysis with oxidative workup gives carboxylic acid(s) Ozonolysis of Alkenes Oxidation of Alkynes Upon oxidation of an alkyne, the C≡C triple bond can be cleaved completely. All three C–C bonds are oxidized to form three new C–O bonds, resulting in carboxylic acid products. This oxidation can be carried out either by ozonolysis or with KMnO4 (dihydroxylation occurs, followed by additional oxidative cleavage).