Organic Chemistry 1 Reactions (UT CH 320M Shabbir)

Alkene > Haloalkane (Markovnikov)

HX (Cl or Br)

Alkene > Alcohol (Markovnikov)

H2O, Cat H2SO4

Alkene > Haloalkane (Antiproduct, 2 halogens on adjacent carbons)

X2 (Cl or Br)

Alkene > Halohydrin (-OH(on most substituted carbon) and Halogen group)

X2, H2O

Alkene > Alcohol (Markovnikov, Scrambled stereochemistry)

HgOAc, NaBH4

Alkene > Alcohol (Non-Markovnikov, Syn Product)

BH3, H2O2

Alkene > double bond broken and each end having a double bond to O

O3, (CH3)2S

Alkene > Vicinal Diol (2 adjacent syn-product -OH groups)

OsO4, NaHSO3

Alkene > Alkane (syn hydrogen groups)

H2, Pd

Alkyne > Alkene > Alkane (geminal dihalide)

HX (Cl or Br) (1 mole/2 mole)

Alkyne > ketone (-CHO, Non-Markovnikov)

Sia2(BH), H2O2 (Keto-Enol Tautomerization)

Alkyne > Alkene (Antiproduct, radical)

Na, NH3

Alkane > Bromoalkane (stable carbon radical)

Br2, hv (initiation > propagation)

Alkene > Bromoalkene (forms most stable double bond)

NBS, hv

Alkene > bromoalkane (Non-Markovnikov, scramble double bond to make most stable carbon radical)

HBr, H2O2

Simultaneous addition of nucleophile and departure of leaving group

Sn2 (occurs more frequently with strong nucleophile, polar aprotic solvent, primary/secondary halides)

Simultaneous removal of proton and departure of leaving group (Zaitsev, anti-periplanar geometry)

E2 (occurs more frequently with strong base)

Removal of leaving group then mixed addition of nucleophile and removal of proton (3 products, Zaitsev or possible carbocation rearrangement)

Sn1/E1 (occurs more frequently with weak nucleophiles, weak bases, polar protic solvents, secondary/tertiary halides)

Tertiary alcohol > haloalkane (Sn1, both enantiomers)

HX (Cl or Br)

Alcohol > Alkene (Zaitsev, E-Product)

acid catalyzed (H2SO4)