WWU Chemistry ALDEHYDES AND KETONES I. Nucleophilic Addition to Carbonyl Chapter 16

WWU Chemistry Reading Assignment SKIP: Section 16.8 SKIP: Section I will be covering the remaining sections.

WWU Chemistry Problem Assignment In-Text Problems 16.1 and 2 3 (except for d) End-of-Chapter (all but b) 8 b, c, d 1012

WWU Chemistry Nomenclature of ketones 2,5-dimethyl-3-hexanone

WWU Chemistry 2,5-dimethyl-5-hexen-3-one

WWU Chemistry 2,6-dimethyl-1,4-cyclohexanedione

WWU Chemistry 5,6-dimethyl-5,7-octadien-3-one

WWU Chemistry 5-bromo-2-methylacetophenone

WWU Chemistry Some Common Names of ketones

WWU Chemistry 3,4-dimethylpentanal Nomenclature of aldehydes

WWU Chemistry 3,4-dimethyl-3,5-hexadienal

WWU Chemistry 4,5-dimethyl-2,4-heptadienedial

WWU Chemistry 3,4-dibromobenzaldehyde

WWU Chemistry Some common names of aldehydes

WWU Chemistry Sect. 16.5: Nucleophilic Addition to Carbonyl -- in base

WWU Chemistry Nucleophilic Addition to Carbonyl -- in Acid

WWU Chemistry Sect. 16.6: Addition of Cyanide

WWU Chemistry Sect. 16.7: Addition of Organometallic Reagents

WWU Chemistry Synthesis of Alcohols using Grignard reagents - revisited ketonetertiar y alcohol

WWU Chemistry Synthesis of Alcohols The type of alcohol depends on whether you use formaledhyde, another aldehyde, or a ketone. formaldehyde other aldehydes ketones primary alcohol tertiary alcohol secondary alcohol RMgX + Reaction of RMgBr with aldehydes and ketones yields alcohols

WWU Chemistry Sect. 16.9: Addition of Water

WWU Chemistry Sect : Addition of Alcohols

WWU Chemistry Formation of Acetals

WWU Chemistry A popular acetal!

WWU Chemistry Sect : Protective groups

WWU Chemistry Sect : Addition- Elimination: The Formation of Imines

WWU Chemistry Formation of Simple Imines

WWU Chemistry Formation of Oximes hydroxylamine an oxime

WWU Chemistry Formation of Hydrazones a hydrazine

WWU Chemistry 2,4-Dinitrophenylhydrazones 2,4-dinitrophenylhydrazine

WWU Chemistry Formation of Semicarbazones semicarbazide

WWU Chemistry Addition-Elimination: The Formation of Imines

WWU Chemistry Sect : Formation of Enamines

WWU Chemistry Enamine Formation (Part One)

WWU Chemistry Enamine Formation (Part Two)

WWU Chemistry Nucleophilic Character of Enamines

WWU Chemistry Reactions of Enamines as Nucleophiles

WWU Chemistry Hydrolysis of Iminium Salts (Part One)

WWU Chemistry Hydrolysis of Iminium Salts (Part Two)

WWU Chemistry Enamine Reactions -- Summary

WWU Chemistry Gilbert Stork, developed enamine chemistry and also did a total synthesis of Quinine C & E News, 26 Feb, 2007

WWU Chemistry Quinine has four stereocenters! Source of picture: Michigan State University, Department of Chemistry ollection.shtml

WWU Chemistry William Doering (left) and R.B. Woodward, Harvard, synthesized precursor to quinine, Notice the cigarette! Woodward won the Nobel Prize in 1965.

WWU Chemistry Woodward (left) and Doering discussing the synthesis of quinine.

WWU Chemistry K. B. Wiberg, Yale University, Lampman’s Ph.D. adviser. Wiberg was a Ph.D. student of Doering.

WWU Chemistry Lampman chemical genealogy

WWU Chemistry Gabrielle Fallopio

WWU Chemistry Justus von Liebig

WWU Chemistry August Wilhelm von Hofmann

WWU Chemistry Lampman chemical genealogy

WWU Chemistry Sect : The Wittig Reaction

WWU Chemistry Ylide A compound or intermediate with both a positive and a negative formal charge on adjacent atoms.

WWU Chemistry Resonance in Ylides

WWU Chemistry Mechanism

WWU Chemistry Preparation of the Ylide

WWU Chemistry George Wittig, nobel prize, 1979

WWU Chemistry Carbohydrates Sections

WWU Chemistry Emil Fischer Source: Michigan State University, Department of Chemistry

WWU Chemistry Norman Haworth Source: Michigan State University, Department of Chemistry

WWU Chemistry Sect : Cyclization of Monosaccharides

WWU Chemistry Alpha D(+) glucose

WWU Chemistry Beta D(+) glucose

WWU Chemistry Mutarotation of Glucose

WWU Chemistry  -1,4-Glycosidic Linkage

WWU Chemistry  -1,4-Glycosidic Linkage

WWU Chemistry Sucrose