Download Reactions of Alcohols

Reactions of Alcohols
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Reaction Summary:
4. Hydration: Alkene + water --> alcohol
7. Dehydration: Alcohol + heat --> alkene + H2
8. Oxidation: Pri. Alcohol + (O) --> aldehyde
9. Oxidation: Sec. Alcohol + (O) --> ketone
9B. Oxidation: Tert. Alcohol + (O) --> no reaction
10.Oxidation: Aldehyde + (O) --> Acid
11. Ether Synthesis: Alcohol + alcohol --> ether +
HOH
4. Hydration Reaction
• Alkene + HOH --> alcohol
• HOH molecule adds to carbons with double bond.
H3C
H3C
CH CH3
H
C
CH2
+
HOH
H3C
H
C
HO
C
H
H
HO
H
Mark's Rule
H
H3C
C
H
C
OH H
H
7. Dehydration of Alcohol to Alkene
• Subtraction: Remove -OH from alcohol carbon
• Remove -H from a neighbor carbon
H
H3C
CH OH
H3C
H
H
H
H
H
C
C
H3C
O
CH2
OH
H 3C
CH
Reactions of Alcohols
8. Oxidation of Primary Alcohol to Aldehyde
• Subtraction: Remove -H from alcohol group
• Remove -H from alcohol carbon
H
H3 C
H2
C
C
H2
OH
H2 H
O
C
H3C
C
O
H
(O)
+
H
H
H3C
H2
C
O
C
H
Reactions of Alcohols
9. Oxidation of Secondary Alcohol to Ketone
• Subtraction: Remove -H from alcohol group
• Remove -H from alcohol carbon
H
H3C
H
H
OH
CH
O
O
CH3
H3C
C
H
+ (O)
CH3
O
H3C
C
CH3
Reactions of Alcohols
Reactions of Alcohols
Reactions of Alcohols
Reactions of Alcohols
Reactions of Alcohols
CH3
CH
H3C
CH3
CH
+ (O)
OH
CH3
H2C
H3C
CH
H2C
H2
C
H3C
+ (O)
OH
H2
C
+
SH
H 3C
+ (O)
SH
10. Oxidation of Aldehyde to Acid
• Add oxygen from oxidizing agent
• Insert O between H of carbon double oxygen
H3C
H2
C
O
C
H
H3C
H2
C
C
O
+ (O)
H
O
H 3C
C
H2
C
OH
11. Ether synthesis from 2 alcohols
• Subtraction: Remove -H from one alcohol group
• Remove -OH from other alcohol carbon
• Join two parts
O
H
H3C
H2
C
O
H
+ HO
H2
C
CH3
H3 C
H2
C
O
H
H2
C
CH3
Reactions of Alcohols
CH3
CH3
HO CH
CH3
+
HO CH
CH3