Organic Chemistry I Mechanisms’ Reagents – Chapter 6 & 7

question

No Shifts Means …
answer

No True Carbocation
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Oxymercuration Reduction (Alkene to Alkane)
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1. HgOAC2, H2O / 2. NaBH4 … More Substituted, No Shifts
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Acid-catalyzed Hydration (Alkene to Alkane)
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HgSO4 / H2O … More Substituted, Shift
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Hydroboration-oxidation (Alkene to Alkane)
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1. BH4 x THF / 2. H2O2, NaOH … Less substituted, No Shifts
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Acid-catalyzed Hydration (Alkyne to Alkene)
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HgSO4 / H2SO4, H2O …. More Substituted, No Shifts (goes to Ketone, never an Aldehyde)
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Hydroboration-oxidation (Alkyne to Alkene)
answer

1. (sia)2 BH / 2. H2O2, NaOH …. Less substituted, No Shifts (goes to Aldehyde on terminal alkyne & Ketone on internal alkyne)
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Catalytic Reduction (Alkene to Alkane)
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H2 / Pt (takes Alkene and makes it Alkane)
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Hydroboration-Protonolysis (Alkyne to Cis Alkene)
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1. BH3 x THF / 2. CH3COOH (Alkyne to cis Alkene)
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Dissolving-Metal Reduction
answer

H2 / Lindlar’s Catalyst (Alkyne to Cis Alkene) 2 Na / NH3 (Alkyne to Trans Alkene)

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