Alkene Reactions & Carboxylic Acid Derivatives

H-X

Hydrohalogenation conditions

H, X

What does hydrohalogenation (H-X) add to an alkene?

both

Does hydrohalogenation (H-X) add H, X syn or anti?

yes

Can rearrangement happen with hydrohalogenation (H-X)?

more substituted carbon (markovnikov)

Where does the halogen (X) add in hydrohalogenation (H-X)?

H2SO4, H2O

Hydration conditions

H, OH

What does hydration (H2SO4, H2O) add to an alkene?

both

Does hydration (H2SO4, H2O) add H, OH syn or anti?

yes

Can rearrangement happen with hydration (H2SO4, H2O)?

more substituted carbon (markovnikov)

Where does the alcohol (OH) add in hydration (H2SO4, H2O)?

Hg(OAc), H2O/R-OH, NaBH4

Oxymercuration demercuration conditions

H, OH/OR

What does oxymercuration demercuration (Hg(OAc), H2O/R-OH, NaBH4) add to an alkene?

both

Does oxymercuration demercuration (Hg(OAc), H2O/R-OH, NaBH4) add H, OH/OR syn or anti?

no

Can rearrangement happen with oxymercuration demercuration (Hg(OAc), H2O/R-OH, NaBH4)?

more substituted carbon (markovnikov)

Where does the alcohol/etc. (OH/OR) add in oxymercuration demurcuration (Hg(OAc), H2O/R-OH, NaBH4)?

BH3, H2O2, NaOH, H2O

Hydroboration oxidation conditions

H, OH

What does hydroboration oxidation (BH3, H2O2, NaOH, H2O) add to an alkene?

syn

Does hydroboration oxidation (BH3, H2O2, NaOH, H2O) add H, OH syn or anti?

no

Can rearrangement happen with hydroboration oxidation (BH3, H2O2, NaOH, H2O)?

less substituted carbon (anti-markovnikov)

Where does the alcohol (OH) add in hydroboration oxidation (BH3, H2O2, NaOH, H2O)?

OsO4, NaHSO3, H2O

Dihydroxylation conditions

OH, OH

What does dihydroxylation (OsO4, NaHSO3, H2O) add to an alkene?

syn

Does dihydroxylation (OsO4, NaHSO3, H2O) add OH, OH syn or anti?

no

Can rearrangement happen with dihydroxylation (OsO4, NaHSO3, H2O)?

H2, cat. Pd/C

Hydrogenation conditions

H, H

What does hydrogenation (H2, cat. Pd/C) add to an alkene?

syn

Does hydrogenation (H2, cat. Pd/C) add H, H syn or anti?

no

Can rearrangement happen with hydrogenation (H2, cat. Pd/C)?

X2 (Cl, Br, I)

Halogenation conditions

X, X

What does halogenation X2 (Cl, Br, I) add to an alkene?

anti

Does halogenation X2 (Cl, Br, I) add X, X syn or anti?

no

Can rearrangement happen with halogenation X2 (Cl, Br, I)?

X2, H2O/R-OH

Halohydrin formation conditions

X, OH/OR

What does halohydrin formation (X2, H2O/R-OH) add to an alkene?

anti

Does halohydrin formation (X2, H2O/R-OH) add X, OH/OR syn or anti?

no

Can rearrangement happen with halohydrin formation (X2, H2O/R-OH)?

more substituted carbon (markovnikov)

Where does the alcohol, etc. (OH/OR) add in halohydrin formation (X2, H2O/R-OH)?

mCPBA, strong nuc, H3O+

Epoxide + Ring-opening conditions

OH, Nuc

What does epoxide + ring-opening (mCPBA, strong nuc, H3O+) add to an alkene?

anti

Does epoxide + ring-opening (mCPBA, strong nuc, H3O+) add OH, Nuc syn or anti?

no

Can rearrangement happen with epoxide + ring-opening (mCPBA, strong nuc, H3O+)?

more substituted carbon (markovnikov)

Where does the alcohol (OH) add in epoxide + ring-opening (mCPBA, strong nuc, H3O+)?

R-OH, cat. HCl

carboxylic acid + ____________ = ester

acid or base, H2O

R-CN + _____________ = carboxylic acid

acid or base, H2O

amide + _____________ = carboxylic acid

acid or base, H2O

ester + _____________ = carboxylic acid

R-OH, pyridine

acid chloride + ______________ = ester

HNR2, pyridine

acid chloride + __________ = amide

acid or base, H2O

acid chloride + ___________ = carboxylic acid

SOCl2

carboxylic acid + ____________ = acid chloride