reagents/solvents

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Last updated 4:51 PM on 6/30/26
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5 Terms

1
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catalytic H2SO4, H2O

  • regioselectivity (where does H and OH add?)

    • markov.

  • stereospecificty

    • none/random

  • rearrange?

    • yes

  • functional group

    • tertiary alcohol

<ul><li><p>regioselectivity (where does H and OH add?)</p><ul><li><p>markov.</p></li></ul></li><li><p>stereospecificty</p><ul><li><p>none/random</p></li></ul></li><li><p>rearrange?</p><ul><li><p>yes</p></li></ul></li><li><p>functional group</p><ul><li><p>tertiary alcohol </p></li></ul></li></ul><p></p>
2
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oxymercuation/demercuration

  1. Hg(OAc)2, H2O (bridged)

  2. NaBH4

  • regioselectivity (where does H and OH add?)

    • markov.

  • stereospecificty

    • anti

  • rearrange?

    • no

  • functional group

    • secondary alcohol

    • racemic

<ul><li><p>regioselectivity (where does H and OH add?)</p><ul><li><p>markov.</p></li></ul></li><li><p>stereospecificty</p><ul><li><p>anti</p></li></ul></li><li><p>rearrange?</p><ul><li><p>no</p></li></ul></li><li><p>functional group</p><ul><li><p>secondary alcohol</p></li><li><p>racemic </p></li></ul></li></ul><p></p>
3
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oxymercuration/demercuration

  1. Hg(OAc)2, ROH

  2. NaBH4

  • regioselectivity (where does H and OH add?)

    • markov.

  • stereospecificty

    • anti

  • rearrange?

    • no

  • functional group

    • ether racemic

<ul><li><p>regioselectivity (where does H and OH add?)</p><ul><li><p>markov.</p></li></ul></li><li><p>stereospecificty</p><ul><li><p>anti</p></li></ul></li><li><p>rearrange?</p><ul><li><p>no</p></li></ul></li><li><p>functional group</p><ul><li><p>ether racemic</p></li></ul></li></ul><p></p>
4
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hydroboration/oxidation

  • regioselectivity (where does H and OH add?)

    • anti-markov.

  • stereospecificty

    • anti

  • rearrange?

    • no

  • functional group

    • primary alcohol

<ul><li><p>regioselectivity (where does H and OH add?)</p><ul><li><p>anti-markov.</p></li></ul></li><li><p>stereospecificty</p><ul><li><p>anti</p></li></ul></li><li><p>rearrange?</p><ul><li><p>no</p></li></ul></li><li><p>functional group</p><ul><li><p>primary alcohol</p></li></ul></li></ul><p></p>
5
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