Ch 8 Alkene Addition rxns

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16 Terms

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<p>Hydrohalogenation </p>

Hydrohalogenation

H-X is regioselective (mark +). IF carbocation RAR possible then a mix of products is obtainted. Not really super useful

<p>H-X is regioselective (mark +). IF carbocation RAR possible then a mix of products is obtainted. Not really super useful </p>
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<p>Hydrohalogenation 1</p>

Hydrohalogenation 1

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<p>Hydrohalogenation 2 (Be careful peroxides)</p>

Hydrohalogenation 2 (Be careful peroxides)

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<p>Acid-Catalyzed Hydration </p>

Acid-Catalyzed Hydration

Markovnikov + of H and OH over alkene. Synthetically very useful.

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<p>Reversal of alcohol to alkene. Elination reaction</p>

Reversal of alcohol to alkene. Elination reaction

Uses heat=less h2o or just a more concentrated acid

<p>Uses heat=less h2o or just a more concentrated acid</p>
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<p>Oxymercuration-demurcuration</p>

Oxymercuration-demurcuration

Markovnikov addition of H and OH across alkene without carbocation rar

<p>Markovnikov addition of H and OH across alkene without carbocation rar</p>
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<p>Hydroboration oxidation</p>

Hydroboration oxidation

Anti Markovnikov addition of H and OH across alkene. Syn addition.

<p>Anti Markovnikov addition of H and OH across alkene. Syn addition.</p>
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<p>Hydroboration Oxidation</p>

Hydroboration Oxidation

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<p>Hydrogenation</p>

Hydrogenation

gives syn addition of H’s over alkene. Reduces double and triple bonds to single bonds. Only makes syn products in cases where stereo centers are formed

<p>gives syn addition of H’s over alkene. Reduces double and triple bonds to single bonds. Only makes syn products in cases where stereo centers are formed</p>
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<p>Bromination</p>

Bromination

Anti addition over alkene of Br and Br over alkene

<p>Anti addition over alkene of Br and Br over alkene</p>
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<p>Halohydrin formations</p>

Halohydrin formations

anti addition of Br and OH across the alkene with OH being installed at the more substituted position. 3 ring bridged intermediate is attacked by OH.

<p>anti addition of Br and OH across the alkene with OH being installed at the more substituted position. 3 ring bridged intermediate is attacked by OH. </p>
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<p>Anti dihydroxylation. MCPBA  and Ch3CO3H (peroxyacetic acid) are both peroxy acids (strong oxidizing agents)</p>

Anti dihydroxylation. MCPBA and Ch3CO3H (peroxyacetic acid) are both peroxy acids (strong oxidizing agents)

Epoxide intermeidate. Ring opening to form trans-diol via aqueous acid.

<p>Epoxide intermeidate. Ring opening to form trans-diol via aqueous acid.</p>
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<p>Syn Dihydroxylation: KMnO4, NaOH, Cold</p>

Syn Dihydroxylation: KMnO4, NaOH, Cold

Gives the same OH and OH over the alkene. KMnO4 is a strong oxidizing agent and can cause further oxidation of the diol so OsO4 is used more often

<p>Gives the same OH and OH over the alkene. KMnO4 is a strong oxidizing agent and can cause further oxidation of the diol so OsO4 is used more often</p><p></p>
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Ozonolysis

Cleavage of C=C sp2 bonds can open a ring or make two products with a c=o in place of the other Carbon in the C=C bond