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Acetal

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Hemiacetal

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Imine

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Oxime

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Hydrazone

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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

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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

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Thioacetal

Formation of a cyclic thioacetal

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

Formation of a cyanohydrin

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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)

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Lactone (cyclic ester)

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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