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Advanced Organic Chemistry by Warren

By Warren

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Oxidizing agents that aren’t strong enough to oxidize the aldehyde formed in the first step include PCC (pyridinium chlorochromate), Sarett’s reagent (CrO3•2py), and acidic, aqueous potassium dichromate (K2Cr2O7). The reaction with potassium dichromate requires the distillation of the aldehyde from the mixture before further oxidation can occur. Two examples are in Figure 3-20. Figure 3-19: Oxidation of a primary alcohol to an aldehyde R-CH2OH and then to an carboxylic acid. Figure 3-20: Example of the oxidation of a primary alcohol to an aldehyde.

Basic conditions may yield anionic or neutral products. ✓ Watch out for those pesky five-bonded carbon atoms. ✓ When you finish the mechanism, go over each step and check your assumptions. Make sure none of your intermediates are unstable. 29 30 Part I: Brushing Up on Important Organic Chemistry I Concepts Chapter 3 Alcohols and Ethers: Not Just for Drinking and Sleeping In This Chapter ▶ Checking out alcohols: How they look and what they’re called ▶ Taking a look at the synthesis and reactions of alcohols ▶ Tackling the basics of ethers ▶ Finding out what ethers do ▶ Clarifying the spectra of alcohols and ethers T wo types of organic compounds contain single-bonded oxygen atoms: the alcohols and the ethers.

Other than radicals, the electrons in the orbitals are either bonding pairs or lone pairs. This means that the tail of the curved arrow must be at a lone pair or a bonding pair. ) The head of the curved arrow indicates where a lone pair is going or where a bond will form. Getting Ready for Some Basic Moves The tail of a curved arrow has two possible positions, and the head of a curved arrow has two possible positions. This means that, in theory, four combinations are possible. These combinations are ✓ Bond → lone pair ✓ Bond → bond ✓ Lone pair → bond ✓ Lone pair → lone pair The last combination doesn’t work, at least not in a single step, because it tends to force an atom to exceed an octet.

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