Reagents

LDA

does E2, if LG and H have different stereochem, then E, if same Z

Conc. HCl and heat

SN2, removes an alcohol and adds a chlorine, stereorandom, but can have carbocation rearrangement

HCl

Addition, Epoxide opening

Conc. H2SO4 and heat

Elimination reaction with OH (E1), so both E and Z products

NaH

with an electrophile that has an alcohol and good leaving group and creates an epoxide.

a) NaH b) R - LG

Adds a carbon chain to the oxygen in an alcohol group

Excess NaNH2, heat

Elimination reaction until it can’t (will remove multiple halogens from an alkene to create an alkyne)

a) NaNH2 b) R - LG

Adds R carbon chain

Br2 (includes other halogens)

Adds Br to both carbons in the double bond (on opposite stereochem)

Br2, H2O

Adds Br to least substituted carbon, and OH to most substituted (opposite stereochems)

a)Hg(OAc)2, H2O, b)NaBH4

Addition that adds an OH to the most substituted carbon, but does not do carbocation rearrangement

C2MgBr

Opens expoxide (leaves an OH group)

a) Li - R b) H+

Adds carbon chain to a carbonyl, racemic

LiAlH4

Does aldehyde to alcohol (primary), ketone to alcohol (secondary), and expoxides to alcohols

a) NaBH4 b) H+

Aldehyde or Ketone into alcohol (ketone turns into a racemic alcohol)

mCPBA

Makes alkenes into epoxides (racemic)

a)BH3 b)HOO-

Adds OH to Alkenes (on least substituted carbon

a)O3 b)DMS

Cuts at the double bond and puts oxygen at the end (both ends)

a)OsO4 b)NaOH, H2O

Adds 2 OH groups to alkene, with the same stereochem

CH2N2

turns alkene into a 3 carbon triangle (like expoxide, but no oxygen)

H+, H2O, heat

Turns alkyne into ketone

HgSO4

turns alkyne into a ketone

a)Hb(SiN)2 b)HOO-

turns alkyne into an aldehyde

Br2, light

radical reaction, adds Br to the molecule on the most substituted carbon

Cl2, light

adds Cl to molecule, but creates a mixture because it does not have regiospecificity

HBr + ROOR + light

adds Br to least substituted carbon of a double bond

H2, Pd

turns alkynes and alkenes into alkanes

H2, Lindlars

Alkynes to Z alkenes

Li, NiH3(I)

Alkynes to E alkenes

Mg and Li

Makes Grignard with carbon chains that have leaving groups Br, Cl, or I