alkene reagents

base, heat

ex. (CH₃)₂CO^-K⁺

dehydrohalogenation (loss of HX to form alkene)

NaI, acetone

dehalogenation (loss of X₂ to form alkene)

conc. H₂SO₄ OR H₃PO₄, heat

dehydration of alcohol (loss of OH & H to become alkene)

heat, catalyst

ex. Pt, 500 degrees C

dehydrogenation of alkane (loss of H₂ to form alkene)

HX

halide addition, markovnikov (+ enantiomer)

HBr in peroxide

halide addition w/ anti-markovnikov

H₂O, H⁺

ex. H₂SO₄

acid-catalyzed hydration, markovnikov

Hg(OAc)₂, H₂O, NaBH₄

oxymercuration-demercuration, markovnikov, no rearrangements (+ enantiomer)

Hg(OAc)₂, ROH, NaBH₄

ex. Hg(OAc)₂, CH₃OH, NaBH₄

alkoxymercuration-demercuration, markovnikov, no rearrangements

BH₃ * THF, H₂O₂, OH^-

hyboration-oxidation, anti-markovnikov syn addition, added at the same time

X₂

halogen addition, anti addition

NBS, hv

allylic bromination bc only trace Br₂

X₂, H₂O

halohydrin, markovnikov, anti addition

RCOOOH

epoxidation, creates epoxide ring & acid

RCOOH, H⁺, H₂O

ex. HCOOOH, H₃O⁺

anti dihydroxylation, adds OH anti to each other (+ enantiomer OR meso compound)

(step 1: epoxide formation; step 2: acid-catalyzed epoxide ring opening)

OsO₄, H₂O₂ OR

KMnO₄(cold, dilute), OH^-, H₂O

syn dihydroxylation, adds OH syn to each other (+ enantiomer)

O₃, (CH₃)₂S

ozonolysis, forms ketone and aldehyde

KMnO₄, warm

potassium permanganate, forms ketone and acid

Ru or Mo, catalyst

olefin metathesis, takes left and right of two atoms and makes a cis & trans version of it + ethylene

H₂, (Pt, Pd, Ni)

catalytic hydrogenation, adds H₂ syn to each other

CHBr₃, NaOH/H₂O

carbene addition, adds CBr₂ in a ring structure to the alkene side