CHEM 2370 Ch. 8 & 9, All reactants

R: alkene + H2, metal catalyst, pressure

P: syn H addition alkane

R: alkene + H2SO4 or H3PO4 + H2O

P: carbocation intermediate w/ rearrangement → alkane w/ mark OH where carbocation was and H

R: alkene + Hg(OAc)2 + THF/H2O + NaBH4, OH-

P: 3 membered mercurinium ion intermediate → alkane w/ mark OH and H

R: alkene + BH3 + THF + H2O2 + OH-

P: square H-BH2 intermediate → alkane w/ syn, anti-mark OH and H

R: alkene + HBr or HI

P: carbocation intermediate w/ rearrangement → alkane w/ mark halogen where carbocation was and H

R: alkene + HBr or HI + peroxide

P: alkane w/ anti-mark halogen and H

R: alkene + Br2 or Cl2

P: bromonium ion intermediate → alkane with inverted anti-addition halogens + enantiomer

R: alkene + Br2 or Cl2 + H2O

P: bromonium ion intermediate → alkane w/ anti-addition halogen and OH w/ OH on higher degree carbon + enantiomer

R: alkene + CH2I2 + Zn(Cn)

P: carbene intermediate → syn alkane cyclopropane

R: alkene + diiodomethane + Zn(Cn)

P: carbene intermediate → syn alkane cyclopropane

R: E alkene + OsO4 + pyridine + NaHSO3/H2O

P: alkane w/ syn OH groups + enantiomer

R: Z alkene + KMnO4 + OH- + cold + H2O

P: alkane w/ syn addition OH groups + enantiomer

R: alkene + KMnO4 + OH- + heat + H3O+

P: ketone and/or carboxylic acid

R: alkene + O3 + CH2Cl2 + -78°C + Me2S

P: ketone and/or aldehyde

R: alkyne + H2 + metal catalyst + pressure

P: alkane

R: alkyne + H2 + Ni2B or P-2

H syn addition to alkene

R: alkyne + Pd + CaCO3 + H2 + Quinoline

P: H syn addition to alkene

R: Lindlar’s catalyst

P: H syn addition to alkene

R: alkyne + Li or Na + NH3Cl or CH3CH2NH2

P: H anti addition to alkene

R: alkyne + excess X2

P: halogen anti-addition to alkene intermediate → alkane w/ 4 halogen

R: alkyne + excess HX

P: 2 alkene w/ H and X on either side intermediate → 2 alkane w/ 2 H and 2 X on either side

R: alkyne + Hg2+ + H3O+ + H2O

P: mark enol intermediate → ketone

R: alkyne + BH3 + THF + H2O2 + OH-

P: anti mark enol intermediate → aldehyde

R: alkyne + KMnO4 + OH- + H3O+ + heat

P: carboxylic acid + CO2

R: alkyne + O3 + CH2Cl2 + -78°C + Me2S

P: 2 carboxylic acids

R: alkyl halide + excess NaNH2 or a SB/SN + H3O+

P: alkene halide intermediate → terminal alkyne intermediate → deprotonated terminal alkyne intermediate → terminal alkyne

R: terminal alkyne + NaNH2 or a SB/SN

P: alkynide ion

R: alkynide ion + 1° alkyl halide

P: alkyne w/ alkane from alkyl halide attached, halogen has left

R: alkynide ion + 2° alkyl halide

P: protonated terminal alkyne from ion + alkene from alkyl halide

R: 1° alkyl halide + unhindered alkoxide

P: ether

R: alcohol + NaH

P: alkoxide + H2

R: alcohol + NaH + 1° alkyl halide

P: ether

R: halohydrin + NaH

P: O- where OH group was and Br leaving intermediate → inversion, epoxide

R: alcohol + H2SO4 + heat

P: alkene w/o OH group

R: alcohol + POCl3 + pyridine + heat

P: OH+ w/ POCL3 attached intermediate → OHPCl2+ intermediate → OPCl2 intermediate leaves → alkene

R: Me/1° alcohol + HX

P: H2O+ intermediate, SN2 → alkane w/ X in place of H2O

R: 2°/3° alcohol + HX

P: H2O+ intermediate, SN1 → alkane w/ X in place of H2O

R: alcohol + HCl + ZnCl2/catalyst

P: Cl takes place of OH

R: 1°/2° alcohol + SOCl2 + pyridine

P: SN2 inversion alkyl chloride

R: 1°/2° alcohol + PBr3

P: alkyl bromide

R: alcohol + sulfonyl group w/ Cl + pyridine

P: OTs replaces OH group

R: alcohol + SOCl2

P: inversion, Cl replaces OH

R: ether + HBr or HI

P: ROH + RX intermediates → 2RX + H2O

R: ether attached to benzene ring + 2HX

P: OH on benzene ring + RX + HX

R: epoxide + base + H2O

P: SN2, Base w/o its metal on lower degree w/ O- from epoxide on higher → anti OH and base w/o metal

R: epoxide + acid

P: OH replaces epoxide intermediate → conjugate base attached to highest degree carbon and OH on lower degree

R: alkene + peroxy acid/mCPBA

P: syn addition epoxide + enantiomer