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Sterically hinderedHarder to solvate
Easier to solvate
Strong inductive effectStabilizes alkoxide ion
More polarizable sulfer
‘Normal’ O-H pka
Stability of Resonancestructures
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Limitations of the Grignard Reagent: They react with almost anything, therefore you can’t have the
below functional groups on your alkyl halide.
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Converting an alcohol into a tosylate. (this turns the oxygen of the alcohol into a good
leaving group)
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Spectroscopy of Alcohols and Phenols
• Characteristic O–H stretching absorption at 3300 to 3600 cm1 in the infrared
• Sharp absorption near 3600 cm-1 except if H-bonded: then broad absorption 3300 to 3400 cm1 range
• Strong C–O stretching absorption near 1050 cm1 (See Figure 17.11)
• Phenol OH absorbs near 3500 cm-1