Midterm 3 Reaction Predictions

HCl

Cl₂

Cl₂, H₂O

H₃O⁺

HBr, ROOR

2 steps

1) Hg(OAc)₂, H₂O

2) NaBH₄

2 steps

1) BH₃, THF

2) H₂O₂, NaOH

H₂, Pd

Br₂

Br₂, H₂O

2 Steps

1) RCO₃H

2) H₃O+

KMnO₄, NaOH, cold

2 steps

1) OsO₄

2) NaHSO₃, H₂O

2 steps

1) O₃

2) DMS

HX

HX (one equivalent)

2 steps

1) excess NaNH₂

2) H₂O

excess HX

HgSO₄, H₂SO₄, H₂O

2 steps

1) R₂BH

2) H₂O₂, NaOH

X₂ (one equivalent), CCl₄

excess X₂, CCl₄

2 steps

1) O₃

2) H₂O

2 steps

1) NaNH₂

2) RX

Na, NH₃ (l)

H₂, Pd

H₂, Lindlar’s catalyst

NaH

Hint: hydrogen

H₂, Pd

NaBH₄, MeOH

2 steps

1) LiAlH₄

2) H₃O⁺

Hint: hydrogen

H₂, Pd

2 steps

1) LiAlH₄

2) H₃O⁺

NaBH₄, MeOH

2 steps

1) excess LiAlH₄

2) H₃O⁺

2 steps

1) excess LiAlH₄

2) H₃O⁺

2 steps

1) RMgX

2) H₃O⁺

2 steps

1) excess RMgX

2) H₃O⁺

TMSCl, Et₃N

TBAF

HX

Hint: hydrogen

HBr

2 steps

1) TsCl, Pyridine

2) NaBr

PBr₃

Hint: hydrogen

HCl, ZnCl₂

SOCl₂, Pyridine

concentrated H₂SO₄, heat

NaOEt

Na₂Cr₂O₇, H₂SO₄, H₂O

Na₂Cr₂O₇, H₂SO₄, H₂O

2 steps

1) DMSO, (COCl)₂

2) Et₃N

PCC, CH₂Cl₂

2 steps

1) NaH

2) RX

excess HX, heat

2 steps

1) Hg(OAc)₂, ROH

2) NaBH₄

O₂, time

MCPBA

2 steps

1) Br₂, H₂O

2) NaOH

2 steps

1) NaOR

2) H₃O⁺

2 steps

1) NaCN

2) H₃O⁺

2 steps

1) NaSR

2) H₃O⁺

2 steps

1) RMgBr

2) H₃O⁺

2 steps

1) LiAlH₄

2) H₃O⁺

HX

H⁺, H₂O

H⁺, ROH