CHEM 331 Exam 3 Reactions

Alkyne + 2 HX

geminal dihaloalkane (both halogens add to the same carbon)

Alkyne + 2 X₂

tetrahaloalkane (two halogens add to each original alkyne carbon)

Alkyne + 1) (sia)₂BH 2) H₂O₂, NaOH

aldehyde after anti-Markovnikov hydration and tautomerization (terminal alkyne)

Alkyne + 1) BH₃ 2) H₂O₂, NaOH

aldehyde after anti-Markovnikov hydration and tautomerization (terminal alkyne)

Alkyne + H₂SO₄, HgSO₄

ketone after Markovnikov hydration and tautomerization (terminal alkyne gives a methyl ketone)

Alkyne + H₂, Pd, Pt, or Ni

cis addition alkene

Alkyne + H₂, Lindlar catalyst

cis (Z) alkene (partial hydrogenation)

Alkyne + Na, NH₃

trans (E) alkene (dissolving-metal reduction)

Alkene + HX

haloalkane (Markovnikov addition

Alkene + X₂

vicinal dihaloalkane (anti addition

Alkene + X₂, H₂O

halohydrin (anti addition

Alkene + 1) BH₃ 2) H₂O₂, NaOH

alcohol (anti-Markovnikov

Alkene + H₂O, H₂SO₄

alcohol (Markovnikov hydration

Alkene + 1) Hg(OAc)₂, H₂O 2) NaBH₄

alcohol (Markovnikov hydration

Alkene + 1) OsO₄ 2) NaHSO₃

vicinal diol (syn addition)

Alkene + 1) OsO₄ 2) (CH₃)₂S

vicinal diol (syn addition)

Alkene + 1) O₃ 2) (CH₃)₂S

aldehydes and/or ketones formed by cleavage of the C=C bond

Alkane + X₂, hv or heat

haloalkane (radical substitution

Alkane + NBS, hv

allylic halide (allylic radical substitution)

Vicinal dihaloalkane + excess NaNH₂, NH₃

alkyne by two successive eliminations