Alkene Preparation Reactions

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8. Alkynes: An Introduction to Organic Synthesis
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Presentation transcript:

Alkene Preparation Reactions Alkyne reductions Syn orientation Anti orientation Elimination reactions Alcohol dehydration Alkyl halide dehydrohalogenation Vicinal dihalide dehalogenation

Alkenes via Alkyne Reduction Syn reduction of Alkynes to Alkenes Catalytic Hydrogenation using a poisoned catalyst Anti reduction of Alkynes to Alkenes Dissolving Metal reduction

Alkenes via Alkyne Reduction

Alcohol Elimination E-1 Unimolecular kinetics Carbocation intermediates Skeletal rearrangements possible

Alkenes via Alcohol Dehydration

Dehydrohalogenation of Alkyl Halides Unimolecular versus Bimolecular elimination

Bimolecular Dehydrohalogenation of Alkyl Halides Periplanar anti-elimination

Dehalogenation of Vicinal Dihalides Bimolecular kinetics Periplanar Anti-orientation No skeletal rearrangements possible

E-2 Dehalogenation of Vicinal Dihalides Periplanar anti-elimination

Alkyne Preparation Reactions Elimination Vicinal tetrahalide dehalogenation Vicinal dihalide dehydrohalogenation Substitution Alkynyl anion synthesis

Vicinal Tetrahalide Dehalogenation

Vicinal Dihalide Dehydrohalogenation

Substitution Alkynyl Anion Synthesis of Alkynes via Bimolecular Nucleophilic Substitution

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