Chapter 17 ArReaction
Chapter 17 ArReaction
Chapter 17 ArReaction
Compounds
© 2017 Pearson Education, Ltd. Lecture 芳香族化合物的反應
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17-1 Electrophilic Aromatic Substitution (EAS)
H+ + HNO3 + ½ I2 I+ + NO2 +
H2O
• Sulfonation is reversible.
磺化是可逆的
• The sulfonic acid group may be removed from an aromatic
ring by heating in dilute sulfuric acid.
磺酸基團可以通過在稀硫酸中加熱⽽從芳環中除去。
Problem 12
到部分正羰基碳上的碳。
• Since like charges repel, this close proximity of the two positive
charges is especially unstable.
由於類似的電荷排斥,這兩個正電荷的接近是特別不穩定的。
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Meta Attack on Acetophenone
Solution
The amide group (–NHCOCH3) is a strong activating and directing group because the nitrogen atom
with its nonbonding pair of electrons is bonded to the aromatic ring. The amide group is a stronger
director than the chlorine atom, and substitution occurs mostly at the positions ortho to the amide. Like
an alkoxyl group, the amide is a particularly strong activating group, and the reaction gives some of the
dibrominated product.
Solution
The amide group (–NHCOCH3) is a strong activating and directing group because the nitrogen atom
with its nonbonding pair of electrons is bonded to the aromatic ring. The amide group is a stronger
director than the chlorine atom, and substitution occurs mostly at the positions ortho to the amide. Like
an alkoxyl group, the amide is a particularly strong activating group, and the reaction gives some of the
dibrominated product.
Step 1:
Step 2:
Step 3:
© 2017 Pearson Education, Ltd. Problem 17, 19, 45, 46, 47, 48, 49
© 2017 Pearson Education, Ltd.
© 2017 Pearson Education, Ltd.
© 2017 Pearson Education, Ltd.
17-11 Friedel-Crafts Acylation
步驟1:氫氧化物的攻擊產⽣共振穩定的複合物。.
Step 2: Loss of chloride gives the product Step 3: Excess base deprotonates the product
第2步:失去氯化物產⽣的產物。. 步驟3:多餘的鹼使產物去質⼦化.
Problem 59, 74
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© 2017 Pearson Education, Ltd.
17-15 Side-Chain Reactions of Benzene Derivatives
Side-Chain Oxidation