OChem Test 2 Reagents

hydrate formation

H3O+ or H2O & OH

hemiacetal formation

NaOEt & EtOH

acetal formation

EtOH, H+

immine formation

NH3 (optional: H+, Na2SO4, MgSO4)

hydrolysis of immines

H2O, H+

enamine formation

NH3

Wolff Kischner Deoxygenation

H2NNH2, -OH, heat x2

cyanohydrin formation

KCN, HCl

cyanohydrin destruction (idk lol)

base (-OH, pyridine, etc)

wittig reaction

Ph3P=–R

Baeyer-Villiger oxidation

mCPBA

carbonation of organometallic reagents (bunny rabbit rxn)

1. CO2 2. H3O+

conversion of carboxylic acid to acid chloride

SOCl2 or PCl3 or PBr3

carboxylic acid to anhydride

NEt3 or heat

fischer esterification

MeOH, H+

reduction of carboxylic acids

1. LAH 2. H3O+

hydrolysis of acid chlorides

H2O

hydrolysis of anhydrides

H2O

hydrolysis of amides

conc acid/base or heat

hydrolysis of esters

acid/base

hydrolysis of nitriles

conc acid/base, heat

acid chloride/anhydride to ester

NaOMe or MeOH, H+

amidation

NH3, heat/DMAP

conversion of acid chloride/anhydride to ketone

1. Et2LiCu 2. H3O+

conversion of acid chloride/anhydride to aldehyde

1. LiAl(OtBu)3H 2. H3O+

transesterification

EtOH, H+

reduction of amides w/ LiAlH4

1. LiAlH4 2. H3O+

reduction of amides w/ DiBAl

1. DiBAl (1 eq) 2. H3O+

Hoffman rearrangement

KOH, Br2