Carbonyl Rxn and Mechanisms

Carbonyl Rxn and Mechanisms - CFQ PP Carbonyl Chemistry...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
180 Mechanisms Reading Brown and Foote: Sections 15.1, 16.6 – 16.11, 16.13, 16.14 17.4 – 17.8, 18.2 and 18.4 – 18.12 Lecture Supplement Carbonyl Reaction Catalysis (page 50 of this Thinkbook) Suggested Text Exercises Brown and Foote: Chapter 15: 1, 2 Chapter 16: 4 – 11, 12 – 14, 19 – 45, 54 – 68 Chapter 17: 2 – 5, 18 – 43 Chapter 18: 2 – 12, 20 - 53 Optional Interactive Organic Chemistry CD and Workbook Supporting Concepts: Carbonyl Chemistry (p. 70) Mechanisms: Acid Anhydride Hydrolysis (p. 17) Acid-Catalyzed Formation of an Acetal (p. 18) Acid-Catalyzed Formation of a Hemiacetal (p. 19) Acid Chloride Hydrolysis (p. 19) Acid Hydrolysis of an Amide (p. 20) Base Hydrolysis of an Amide (p. 21) Base Hydrolysis of a Nitrile (p. 21) Ester Hydrolysis in Aqueous Base (p. 25) Fischer Esterification (p. 25) Formation of a Cyanohydrin (p. 26) Formation of an Imine from a Ketone (p. 26) Nylon Formation (p. 29) Reaction of an Ester with a Grignard Reagent (p. 31) Reduction of an Amide by LAH (p. 31) Reduction of an Ester by LAH (p. 32) Sodium Borohydride Reduction of a Ketone (p. 32) Wittig Reaction (p. 32) Wolff-Kishner Reduction (p. 32) Reactivity Explorer: Acid Chlorides and Anhydrides (p. 40) Amides (p. 43) Carboxylic Acids (p. 44) Esters (p. 45) Ketones and Aldehydes (p. 46)
Background image of page 1

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

View Full DocumentRight Arrow Icon
CFQ & PP: Carbonyl Chemistry: Survey of Reactions and Mechanisms 181 Concept Focus Questions 1. Shown below is the formation of cyclic glucopyranose from acyclic glucose, an example of the intramolecular formation of a hemiacetal. O OH HO HO HO HO α -D-glucopyranose OH O HO HO HO HO H D-glycose (acyclic) O HO HO HO HO OH β -D-glucopyranose H 2 O H 2 O (a) Show the mechanism of the reaction. (b) Why is the reaction faster in the presence of acid? (c) Why is the reaction faster in the presence of base? (d) How would the reactants be different if this reaction occurred in a living cell? 2. The reaction of retinal and opsin to form rhodopsin, a key step in the chemistry of vision, is an example of imine formation. R NH 2 CH 3 H 3 C H 3 C CH 3 O H CH 3 CH 3 H 3 C H 3 C CH 3 N H CH 3 R opsin (R = rest of protein) retinal H 3 O + rhodopsin (a) Write a mechanism for this reaction. (b) Explain how the mechanism suggests that H 3 O + need be present in only a catalytic quantity for this reaction. 3. Reaction of a carboxylic acid with a large excess of an alcohol in the presence of a strong acid (usually H 2 SO 4 ) is called the Fischer esterification. Ph OH O H 2 SO 4 CH 3 OH Ph OCH 3 O (a) Give two specific reasons why must the carboxylic acid carbonyl be protonated prior to nucleophilic attack. (b) The first step of the mechanism is protonation of methanol and not the carboxylic
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/09/2010 for the course CHEM 30B Chem 30B U taught by Professor Miguelgarciagaribay during the Summer '10 term at UCLA.

Page1 / 23

Carbonyl Rxn and Mechanisms - CFQ PP Carbonyl Chemistry...

This preview shows document pages 1 - 3. Sign up to view the full document.

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