Name That Functional Group!
Acetal
Name That Functional Group!
Hemiacetal
Name That Functional Group!
Imine
Name That Functional Group!
Oxime
Name That Functional Group!
Hydrazone
Name That Functional Group!
Gem-diol (hydroxyl groups are on the same carbon)
Reaction favors starting materials if nucleophile is a weak base (aka a good leaving group)
Alcohols attack carbonyl groups to form acetals. Common catalysts are TsOH and sulfuric acid
Imine formation using primary amine
Hydrazone formation using primary amine
Oxime formation using primary amine
Acetal formation from formaldehyde products are favored with aldehydes
Using cyclic acetal as a protecting group
Cyclic acetal formation, Minus water favor products
Secondary amine forms enamine
Name That Functional Group!
Enamine
Wolff-Kishner Reduction obtain alkane from aldehyde or ketone by forming a hydrazone
Reverse cyclic acetal formation, adding water favor reactants
hydrolysis of acetals to yield ketone or aldehyde
hydrolysis of imine to yield ketone or aldehyde
ALSO WORKS WITH HYDRAZONES AND OXIMES
hydrolysis of enamine to yield ketone or aldehyde
under acidic conditions, an aldehyde or ketone will react with 2 equivalents of thiol to produce a thioacetal
Name That Functional Group!
Thioacetal
Formation of a cyclic thioacetal
Cyclic thioacetal can be desulfurized using Raney nickel, yielding the alkane
Formation of a cyanohydrin
Name That Functional Group!
Cyanohydrin
Formation of a cyanohydrin
LAH REDUCTION: Cyanohydrin to primary amine
Acidification of cyanohydrin yields the carboxylic acid (oxidation)
Wittig Reaction
Benzene ring or electron donating group makes (E)-alkene will be preferred
Wittig Reaction
Benzene ring or electron donating group makes (E)-alkene will be preferred
Horner-Wadsworth-Emmons Reaction (HWE reaction)
phosphonate easter carbanion reagent (HWE reagent) reacts with aldehyde or ketone to yield the (E)-alkene as the major product
Baeyer-Villiger Oxidation
Ketone converted to ester when treated with peroxy acid
Baeyer-Villiger Oxidation
Cyclic ketone to a lactone (cyclic ester)
Name That Functional Group!
Lactone (cyclic ester)
Name That Functional Group!
Acid Anhydride
Forming a carboxylic acid via Grignard reagent and CO2
Preparation of acid chloride
Reverse preparation of acid chloride via hydrolysis
Acid chlorides react with an alcohol to make an ester
"Aminolysis" Acid chloride reacts with an amine to convert to an amide
"Aminolysis" Acid chloride reacts with an amine to convert to an amide. Second equivalent of amine mops up HCl
"Aminolysis" Acid chloride reacts with an amine to convert to an amide . Second equivalent of amine mops up HCl
Acid chloride reduced to alcohol using LAH
Stop the reduction of an acid chloride to an alcohol at the ALDEHYDE stage by using a bulkier hydride reagent
Acid chloride reacts with Grignard reagent and ADDS R GROUP TWICE IN PLACE OF Cl
Gilman reagent replaces chloride with alkyl group
excess heating used to convert carboxylic acid to an anhydride
acid chloride + carboxylate salt turn into anhydride
anhydride to ester
anhydride to amide
anhydride to amide
anhydride to amide
anhydride to alcohol
anhydride to aldehyde
Grignard adds R group twice and creates an alcohol
Gilmen reagent converts anhydride to ketone
carboxylic acid to anhydride
preparation of esters via SN2 reaction
Fischer Esterification
Saponification (hydrolysis using basic conditions) converts ester to carboxylic acid
acid hydrolysis (reverse of Fischer esterification) coverts ester to carboxylic acid
Aminolysis of esters converts ester to amine it is slow and has little synthetic utility
DIBAH Reduction of ester converts ester to aldehyde
LAH reduction of ester converts ester to alcohol
Grignard reacts and converts carbonyl to alcohol and adds R group twice
Amide hydrolyzed to a carboxylic acid
base hydrolysis of amides converts amide to carboxylic acid
LAH reduction removes carbonyl group
Preparation of nitrile using SN2 (does not work with tertiary alkyl halides
thionyl chloride converts amide to a nitrile
nitriles can be hydrolyzed to the carboxylic acid going through an amide intermediate
nitriles can be hydrolyzed to the carboxylic acid in basic conditions
Grignard reagent converts nitriles to a ketone
LAH reductions converts nitriles to a primary amine