403221 alcohol 2 403221 alcohol 5 1 2

����� 403221 -alcohol 2

403221 -alcohol 5

1. 2ปฏกรยากบ Grignard reagent (RMg. X( 403221 -alcohol 16

. 2 ��������� ��� alkene 2. 1 hydration 403221 -alcohol 20

2. 2 hydroboration-oxidation 403221 -alcohol 21

. 3 ��������� �� R-X ����� hydrolysis 403221 -alcohol 22

�������� 403221 -alcohol 23

������ CH 3 OH > 1 o >2 o >3 o ����� p. Ka CH 3 OH H 2 O CH 3 CH 2 OH )CH 3)3 COH ������ 15. 5 15. 7 15. 9 18. 0 403221 -alcohol 25

. 2������ 403221 -alcohol 27

. 3 dehydration 403221 -alcohol 28

. 4������� alkyl halide R-X 3 o ROH S N 1 1 o ROH S N 2 403221 -alcohol 30

S N 2 S N 1 403221 -alcohol 31

reagent ������ RX ��� ROH 403221 -alcohol 33

. 5 esterification 403221 -alcohol 34

. 6 oxidation 1 o alcohol �� H ��� /����� O 403221 -alcohol 35

1 o alcohol • Strong oxidizing agent – KMn. O 4/OH– Na 2 Cr 2 O 7/H+ = H 2 Cr. O 4 (chromic acid – oxidise 1 o alcohol ���� carboxylic acid • Mild oxidizing agent – pyridinium chlorochromate, PCC – Cu. O, ������ – oxidise 1 o alcohol ���� aldehyde 403221 -alcohol 36

2 o alcohol 3 o alcohol ������� oxidation 403221 -alcohol 37

��������. 1 Williamson synthesis R’-X ������� 1 o alkyl halide -X ������� Br, I �������� symmetric ��� asymmetric 403221 -alcohol ether 38

. 2 Dehydration of alcohol • ROH ������� 1 o alcohol • ������ symmetric ether • ������ 403221 -alcohol 39

• Mechanism S N 2 403221 -alcohol 40

Mechanism SN 2 ����� R ������ 3 o alkyl 403221 -alcohol 42

Mechanism SN 1 ������� R ���� 3 o alkyl 403221 -alcohol 43

2. ����� autooxidation 403221 -alcohol 44

Epoxide • 3 -membered cyclic ether 403221 -alcohol 46

����� epoxide. 1������� . 2����� bromohydrin 403221 -alcohol 47

. 3��� peroxyacid 403221 -alcohol 48

������ epoxide . 1������� (acidcatalysed ring opening( Nucleophile ������� H 2 O, ROH ����� 403221 -alcohol 49

mechanism CH 3 OH ���� nucleophile ��������� more substituted carbon ���������� 403221 -alcohol 50

. 2������� (basecatalysed ring opening( Base (Nucleophile) ������� OH-, RO-, 403221 -alcohol d- d+ H , R-Mg. X 51

mechanism OH-, RO-, H-, R-Mg. X ���� nucleophile ��������� less substituted carbon ���������� 403221 -alcohol 52

. 2����� thiourea 403221 -alcohol 55

������ thiol. 1 oxidation . 2������ 403221 -alcohol 56

����� thioether 403221 -alcohol 58

������ thioether oxidation 403221 -alcohol 59