Aromatic Hydrocarbons 1Sulfanilamide (A) H2N H2N NI-12 V/ NH2 Metabolism .HCI Prontosil Cl-13 Sulfamethoxazole The familiar over-the-counter analgesics aspirin, paracetamol and ibuprofen.

Organic Chemistry II 1st Semester, Year 2 (2018-2019) Lecture 1

Aromatic Hydrocarbons 1 Dr Asim A. Balakit Pharmaceutical Chemistry Dept., College of Pharmacy, Babylon University

This lecture is mainly based on: Pharmaceutical Chemistry Edited by Jill Barber & Chris Rostron, Oxford University Press, 2013

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What is aromatic chemistry?!

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To be considered aromatic a compound must:

1- be planar (or close to planar)

2- have 4n+2 π-electrons; this criterion is known as Huckel’s rule

3- be cyclic and fully conjugated

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Why is aromatic chemistry important?!

Prontosil and the sulfa drugs:

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Aspirin

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Prozac and Viagra

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Illegal Drugs: Ecstasy and cannabis

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The chemistry of benzene Electrophilic aromatic substitution:

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The mechanism

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Specific electrophilic aromatic substitution reactions: Nitration

Sulfonation

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Friedel-Crafts reaction – the formation of carbon-carbon bonds: Friedel-Crafts acylation

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Friedel-Crafts alkylation

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To solve the problem:

The next lecture will be about the electrophilic aromatic substitution of substituted benzenes- directing effects.

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