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76 notecards = 19 pages (4 cards per page)

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Chapters 19-20 Organic Chemistry II

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Name That Functional Group!

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Acetal

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Name That Functional Group!

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Hemiacetal

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Name That Functional Group!

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Imine

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Name That Functional Group!

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Oxime

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Name That Functional Group!

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Hydrazone

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Name That Functional Group!

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Gem-diol (hydroxyl groups are on the same carbon)

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Reaction favors starting materials if nucleophile is a weak base (aka a good leaving group)

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Alcohols attack carbonyl groups to form acetals. Common catalysts are TsOH and sulfuric acid

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Imine formation using primary amine

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Hydrazone formation using primary amine

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Oxime formation using primary amine

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Acetal formation from formaldehyde products are favored with aldehydes

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Using cyclic acetal as a protecting group

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Cyclic acetal formation, Minus water favor products

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Secondary amine forms enamine

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Name That Functional Group!

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Enamine

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Wolff-Kishner Reduction obtain alkane from aldehyde or ketone by forming a hydrazone

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Reverse cyclic acetal formation, adding water favor reactants

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hydrolysis of acetals to yield ketone or aldehyde

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hydrolysis of imine to yield ketone or aldehyde

ALSO WORKS WITH HYDRAZONES AND OXIMES

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hydrolysis of enamine to yield ketone or aldehyde

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under acidic conditions, an aldehyde or ketone will react with 2 equivalents of thiol to produce a thioacetal

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Name That Functional Group!

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Thioacetal

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Formation of a cyclic thioacetal

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Cyclic thioacetal can be desulfurized using Raney nickel, yielding the alkane

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Formation of a cyanohydrin

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Name That Functional Group!

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Cyanohydrin

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Formation of a cyanohydrin

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LAH REDUCTION: Cyanohydrin to primary amine

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Acidification of cyanohydrin yields the carboxylic acid (oxidation)

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Wittig Reaction

Benzene ring or electron donating group makes (E)-alkene will be preferred

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Wittig Reaction

Benzene ring or electron donating group makes (E)-alkene will be preferred

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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

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Baeyer-Villiger Oxidation

Ketone converted to ester when treated with peroxy acid

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Baeyer-Villiger Oxidation

Cyclic ketone to a lactone (cyclic ester)

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Name That Functional Group!

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Lactone (cyclic ester)

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Name That Functional Group!

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Acid Anhydride

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Forming a carboxylic acid via Grignard reagent and CO2

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Preparation of acid chloride

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Reverse preparation of acid chloride via hydrolysis

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Acid chlorides react with an alcohol to make an ester

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"Aminolysis" Acid chloride reacts with an amine to convert to an amide

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"Aminolysis" Acid chloride reacts with an amine to convert to an amide. Second equivalent of amine mops up HCl

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"Aminolysis" Acid chloride reacts with an amine to convert to an amide . Second equivalent of amine mops up HCl

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Acid chloride reduced to alcohol using LAH

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Stop the reduction of an acid chloride to an alcohol at the ALDEHYDE stage by using a bulkier hydride reagent

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Acid chloride reacts with Grignard reagent and ADDS R GROUP TWICE IN PLACE OF Cl

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Gilman reagent replaces chloride with alkyl group

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excess heating used to convert carboxylic acid to an anhydride

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acid chloride + carboxylate salt turn into anhydride

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anhydride to ester

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anhydride to amide

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anhydride to amide

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anhydride to amide

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anhydride to alcohol

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anhydride to aldehyde

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Grignard adds R group twice and creates an alcohol

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Gilmen reagent converts anhydride to ketone

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carboxylic acid to anhydride

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preparation of esters via SN2 reaction

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Fischer Esterification

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Saponification (hydrolysis using basic conditions) converts ester to carboxylic acid

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acid hydrolysis (reverse of Fischer esterification) coverts ester to carboxylic acid

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Aminolysis of esters converts ester to amine it is slow and has little synthetic utility

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DIBAH Reduction of ester converts ester to aldehyde

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LAH reduction of ester converts ester to alcohol

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Grignard reacts and converts carbonyl to alcohol and adds R group twice

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Amide hydrolyzed to a carboxylic acid

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base hydrolysis of amides converts amide to carboxylic acid

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LAH reduction removes carbonyl group

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Preparation of nitrile using SN2 (does not work with tertiary alkyl halides

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thionyl chloride converts amide to a nitrile

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nitriles can be hydrolyzed to the carboxylic acid going through an amide intermediate

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nitriles can be hydrolyzed to the carboxylic acid in basic conditions

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Grignard reagent converts nitriles to a ketone

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LAH reductions converts nitriles to a primary amine