big schlong orgo alkene alkynes

anti markov

nucleophile goes to the less substituted c and h goes to more substituted

markov

nucleophile goes to more subt. and H goes to less subst

hydrohalogenation

2 groups added; H+ Cl, Br, I, no steroselectivity, markovnikov, carbocation rearrangements(HCl,HBr,HI), if peroxide (t-BuOOH) than anti markov 

acid catalyzed hydration

H+OH added, markovnikov, carbocation rearrangements(H₂SO₄, H₂O, H₃O)

oxymercuration-demurcuration

H+OH, markovnikov, no carbocation, anti addition(1. (Hg(OAc)₂, H₂O 2. NaBH₄)

Hydroboration oxidation

( 1.BH₃ + THF or B₂H₆ diglyme, 2. H₂O₂, NaOH) , H + OH, Anti-markovnikov, syn addition

acid catalyzed addition of an alcohol

H₂SO₄, Ch₃OH , H + OH, markovnikov, no stereochem, carbocation

1.Hg(OAc)₂, 2. NaBH₄

H + OH, Markovnikov, Anti-addition

H2/ P d/C

2 groups added H + H, not markov or anti, syn addition, racemic if chiral centers,

Br₂ and CCl₄ or CH₂Cl₂

X + X added, anti addition (2nd Br prefers more substituted carbon)

X₂ / H₂O or ROH

X + OH or OR, Markovnikov, Anti addition 

( mCPBA Ch₂Cl₂)

2 bonds from O to C, no markov, syn addition,

1.mcpba, 2. H₃O

OH + OH, no markov, anti addition

1.OsO₄ , 2. NaHSO₃ or Na₂SO₃

OH + OH , no markov, syn addition,

1.O3, CH₂Cl₂ 2. DMS or H₂O₂,

H₂O₂ created ketone and carboxylic acid, DMS or SMe₂ created ketone and aldehyde.

Alkyne H₂,

Pd/C, Pt, or Ni= reduces it to alkane, Lindlar catalyst = stops at cis alkene,Na/NH₃ (l) = stops at trans alkene

catalytic hydrogenation of alkynes with lindlars catalyst

H₂ , Lindlars catalyst —→ reduces to cis alkene

Na, NH₃ (l) alkyne

—> trans alkene

alkynes 1 eq HBr, 2 eq HBr,

markovnikov adding tBuOOH has same anti markov effect

hydrohalogenation alkynes internal alkyne (1 eq HBr)

no markov, no e or z

halogenation of alkynes

1 eq stops at alkene, e or z, 2 eq goes all the way to alkene

acid catalyzed hydration of alkynes

addition of an O carbonyl, markovnikov, if terminal alkyne HgSO₄ and H₂SO₄(dil) , if internal no Hg is needed just SO₄

hydroboration oxidation

1. Sia₂BH or BH₃ THF, 2. H₂O₂ , anti markovnikov, e or z, aldehyde in prdct, internal alkyne not markov or anti markov

terminal alkyne ozonolysis

carboxylic acid and CO₂, 1.O₃ ,2. H₂O

internal alkyne ozonolysis

two carboxylic acids, 1. O₃, 2. H₂O

alkylation of acetylide ions

negative chage attacks the C that LG is on forming a new carbon structure

I₂ and H2O

anti markov , anti addition

Dihalogenation

Br₂ anti additon, no markov