CHEM 242 Weeks 9 Lecture Notes Part 1 - Arenediazonium Salts and Nucleophilic Aromatic Substitution PDF

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Lecture notes from week 9 part 1...

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CHEM 242 - Organic Chemistry Week 9 Part 1 Arenediazonium Salts and Nucleophilic Aromatic Substitution Preparation of the Diazonium Salt

● ○ Alternative reagents are ■ NaNO2 + HCl →𝐻𝑁𝑂2 𝑜𝑟 "𝐻𝑂𝑁𝑂"

Synthesis of Substituted Benzenes Using Arenediazonium Salts

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● Facts about Arenediazonium Salts (Ar-N+≡N) ● They are NOT meta directors! ○ Ar-N+≡N will decompose under EAS conditions ● Their reactions are direct replacements of the N2 group ○ Will either be nucleophilic displacement or Free radical ■ (anything with copper) ■ Thankfully, we don’t need to worry about the mechanism for displacement reactions!!! ● Shown as a “2 step process”

○ ■ Useful when EAS fails ■ No other isomers form

Sandmeyer Reactions

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Arenediazonium Salts are a useful Alternative to EAS

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● ○ One isomer only

Useful for Iodination

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Fluorination of Benzene CANNOT be achieved with EAS

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