Chapter 22 Templates

Chapter 22 Templates -...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
1 Chapter 22 ­ Carbonyl Alpha­Substitution Reactions General Overview: General Reaction Scheme: The carbon adjacent to a carbonyl is designated as the alpha ( α )­carbon Electrophilic substitution occurs at the alpha ( α ) position via one of two possible intermediates:
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
2 Keto­Enol Tautomerism The Difference Between Tautomers and Resonance Forms: The Difference Between Tautomers and Conventional Structural Isomers: A carbonyl compound with a hydrogen on its α- carbon rapidly equilibrates with its enol tautomer Tautomers are structural isomers Resonance forms are representations of contributors to a single structure Tautomers interconvert rapidly while ordinary isomers do not
Background image of page 2
3 Enols: The enol tautomer is usually present in only an extremely small percentage and cannot be isolated It can (and does) serve as a reactive intermediate because it forms so rapidly
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
4 Acid Catalysis of Enolization Mechanism: Bronsted­Lowrey acids catalyze keto­enol tautomerization by protonating the carbonyl and activating the α ­protons
Background image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

Page1 / 23

Chapter 22 Templates -...

This preview shows document pages 1 - 5. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online