1

Common names of some popular alcohols

2

Sterically hinderedHarder to solvate

Easier to solvate

Strong inductive effectStabilizes alkoxide ion

More polarizable sulfer

‘Normal’ O-H pka

Stability of Resonancestructures

3

4

5

6

Limitations of the Grignard Reagent: They react with almost anything, therefore you can’t have the

below functional groups on your alkyl halide.

7

Converting an alcohol into a tosylate. (this turns the oxygen of the alcohol into a good

leaving group)

8

9

10

Example of Phenols

11

12

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

13

14

15

NMR of an alcohol

16

-18 g/mol

-31 g/mol