Organic Chemistry Semester 1 Reaction Review

Primary Alkyl Halide to Alcohol

NaOH

Primary Alkyl Halide to Alkene

NaH or t-BuOK

Primary Alkyl Halide to Ether

NaOCH₃

Primary Alkyl Halide to Thiol

NaSH

Primary Alkyl Halide to Ester

CH₃CO₂Na

Primary Alkyl Halide to Nitrile

NaCN

Alcohol to Primary Alkyl Halide

HBr

Alcohol to Alkyl Tosylate

TsCl with py

Alkyl Tosylate to Alcohol

NaOH

Alkyl Tosylate to Alkene

t-BuOK

Tertiary Alkyl Halide to Alcohol

H₂O

Tertiary Alkyl Halide to Alkene (Zaitsev Product)

NaOH or NaOMe

Tertiary Alkyl Halide to Alkene (Hofmann Product)

t-BuOK

Alcohol to Tertiary Alkyl Halide

HBr

Alcohol to Alkene (Zaitsev Product)

conc. H₂SO₄

Alcohol to Tertiary Alkyl Tosylate

TsCl with py

Tertiary Alkyl Tosylate to Alkene (Zaitsev Product)

NaOH

Tertiary Alkyl Tosylate to Alkene (Hofmann Product)

t-BuOK

Hydrohalogenation (Markovnikov)

HX

Hydrohalogenation (Anti-Markovnikov)

HBr with ROOR

Acid-Catalyzed Hydration

H₃O⁺

Oxymercuration-Demercuration

1) Hg(OAc)₂ with H₂

2) NaBH₄

Hydroboration-Oxidation

1) BH₃ with THF

2) H₂O₂ with NaOH

Hydrogenation

H₂ with Pt

Bromination

Br₂

Halohydrin Formation

Br₂ with H₂O

Anti Dihydroxylation

1) RCO₃H

2) H₃O⁺

Syn Dihydroxylation

1) OsO₄

2) NaHSO₃ with H₂O

or

KMnO₂ with cold NaOH

Ozonolysis

1) O₃

2) DMS

Elimination

1) xs NaNH₂

2) H₂O

Elimination

1) xs NaNH₂

2) H₂O

Hydrohalogenation (two equivalents)

xs HX

Hydrohalogenation (one equivalent)

HX

Acid-Catalyzed Hydration

H₂SO₄ with H₂O (enhanced with HgSO₄)

Hydroboration-Oxidation

1) R₂BH

2) H₂O₂ with NaOH

Halogenation (one equivalent)

X₂ (one equiv.) with CCl₄

Halogenation (two equivalents)

xs X₂ (one equiv.) with CCl₄

Ozonolysis

1) O₃

2) H₂O

Alkylation

1) NaNH₂

2) RX

Hydrogenation

H₂ with Pt

Hydrogenation with Poisoned Catalyst

Na with NH₃ (l ) or H₂ with Lindlar's catalysis