Orgo 2 Test 2 reactions

Acid Catalyzed condesation of alchohols (+ mech)

Prepare ethers by adding alkoxides to primary or methyl alkyl halides. (Williamson ether synthesis)

Alkoxymeruration alkene

acid-catalyzed cleavage of ethers by excess HBr or HI

Claisen Rearrangement

Alkene with peroxyacid (mCBPA).

Provide products and mechanisms for the reaction of vicinal halohydrins in base to form epoxides

Provide products for nucleophilic ring-opening reactions of epoxides involving either anionic nucleophiles or acid-catalyzed reactions of neutral nucleophiles.

Provide missing reagents, products, and a mechanism for the synthesis of thiols by the alkylation and hydrolysis of thiourea.

Provide products of the reaction between an alkane thiolate and an alkyl halide. (SN2)

Provide products or missing reagents for the oxidation of thiols to disulfides using iodine and the reverse reduction using sodium borohydride or zinc/acid.

Synthesize aldehydes from primary alcohols, from alkenes, or from esters

Synthesize ketones by oxidation of secondary alcohols, from the ozonation of alkenes, by addition of water to an alkyne , or from the reaction of an acid chloride and a cuprate

Provide products or missing reagents (but not a mechanism) for the oxidation of aldehydes to carboxylic acids.

Provide products and mechanism for hydration of aldehydes and ketones under either acidic or basic conditions

Provide products and a mechanism for the addition of HCN to an aldehyde or ketone to form a cyanohydrin

Provide products for the reduction of a cyanohydrin to yield a vicinal aminoalcohol.

Provide products and mechanism for the formation of imines from aldehyde or ketone plus primary amine.

(NO BASE)

Provide a product and mechanism for the formation of enamines from aldehyde or ketone plus secondary amine.

aldehydes and ketones with

hydroxylamine

aldehydes and ketones with

hydazine

aldehydes and ketones with

phenolhydrazine

aldehydes and ketones with

semicarbazide

Wolff-Kishner

Provide products and mechanism for the acid-catalyzed formation of acetals (from aldehydes or ketones.)

 Provide products and mechanisms for the conversion of acetals to aldehydes or ketones

Use acetals as protecting groups for synthetic schemes

Synthesize phosphorus ylides from alkyl halides (NBuLi to make it + and -)

Synthesize alkenes using the Wittig reaction of a phosphorus ylide with an aldehyde or ketone.

carbox acid by oxidation primary alc

Strong oxidizer KMNO4 or H2CrO4

carbox by oxididation aldehyde

Na2Cr2O7/H2SO4, KMnO4, CrO4, Tollens’ (Ag), Benedict Reagent (Cu) specifically for aldehyde to carboxylic acid, won’t do OH

Cabrox by ox of benzene C-H

reaction of Grignard, organolithium, or organosodium reagents with CO₂ 

acid catalyzed hydrolysis of a nitrile.

Ozonation of an alkene followed by an oxidative workup will yield ___

Provide a synthesis and mechanism (S_N2) for nitriles from methyl or primary alkyl halides + KCN.

 Provide products or missing reagents for the dehydration of amides to nitriles upon addition of SOCl₂ or P₄O₁₀ or POCl₃.

Provide products, missing reagents, or a mechanism for the dehydration of primary amides to nitriles upon addition of SOCl₂.

Provide products and a mechanism for the reaction of a nitrile with a Grignard followed by an aqueous acidic workup

Provide products and a mechanism for the reduction of nitriles by the addition of LiAlH₄.

carboxylic acids and SOCl₂ or PCl₃. (21.3)

Interconvert between the carboxylic acid derivatives (table)

Provide products and a mechanism for the conversion of carboxylic acids + amines to amides using DCC.

Provide complete electron-pushing mechanisms for any of the carboxylic acid derivative conversions.

show it

Provide products or missing reagents for the reduction of carboxylic acids to _____upon addition of BH₃. (the fastest reducer)

Provide products and a mechanism for the reaction of 2 equivalents of organolithium, organosodium, or Grignard reagents to an acid chloride

Provide the products of the reaction of 1 eq. DIBAL (= DIBAH), cold, with an ester AND to an amide

Provide products and a mechanism for the reduction of amides by LiAlH4. (C=O becomes CH2.)

Provide the products (but not a mechanism) for the addition of an organocuprate to acid chloride