Reaction conditions

R-OH + NaH

NaH deprotonates R-OH

haloalkane + LA

halogen gets taken by LA and forms carbocation

C=O + LDA

LDA deprotonates a to C=O, C=O becomes C-O-Li

alkyne + xBuLi

deprotonates alkyne first, then starts deprotonating others

alkene + epoxide

primary alcohol

alcohol + C=O (H+)

acetal formation, OH attacks PROTONATED C=O, C=O eventually leaves as water

alkene to LEAST SUBSTITUED OH

1. BH3, THF

2. HOOH/H2O/NaOH

R-OH, CrO3, H2SO4

H2CrO4 forms (like H2SO4) and R-OH can attack Cr to form Cr with 5 constituents, usually kicking out water

alkene, Br2

Hydroboration, Br epoxide thing

COO-R + KOH

COOH + RO-

hydroxy alkene + m-CPBA

epoxide forms on same face as OH due to OH-mCPBA H bonding

R-MgBr + CuX (X = halogen)

R-MgBrCu(I) (softens grignard)

OH + TsCl/Pyr

OTs, good LG