Reagents and Their Functions

Orgo Reagents

NaNH2

-Strong base

-Deprotonates

-Prepares alkynes

-Used in alkylation

NaH

-Strong base

-Poor nucleophile

-Used in Williamson reaction

-Deprotonates

-Prepares alkynes

H3O+

-Proton source (protonates)

-Helps prepare alkynes

-Produces a ketone with alkynes (acid catalyzed hydration)

Alkynide ion

-Strong nucleophile

-Used in SN2 reactions for alkylation

MeI and EtI

-Used in alkylation

H2, Pd/C

-Used in hydrogenation

-Reduces double bonds all the way

Lindlar’s Catalyst

-Reduces alkynes to cis alkenes (syn addition)

Na (s), NH3 (l)

-Reduces alkynes to trans alkenes (anti addition)

-Uses radical mechanism with lone electron on Na to form trans

HgSO4

-Catalyst in acid catalyzed hydration

-Not consumed

H2SO4, H2O

-Donates H3O+ to the reaction

-Sometimes used with HgSO4

BH3 THF, H2O2 NaOH (Also R2BH)

-Converts alkene into an alcohol

-Converts alkyne into aldehyde through enol intermediate

O3/H2O

-Used in Ozonolysis (oxidative cleavage)

-Forms SYN diols

(NaHSO3, H2O quenches reaction)

R-MgBr

-Grignard reagent

-Adds an OH and R group to reactions

NaHSO3, H2O

-Quenches diol reaction

NaOCl. CH3COOH (Acetic Acid)

-Oxidizing agent, makes ketones

HCl, ZnCl

-Lucas reagent

-Turns alcohols into alkyl chlorides