Organic Chemistry: Chapter 8: Reactions

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addition reactions of alkenes (HCl, HBr, HI)

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addition reactions of alkenes (HCl, HBr, HI)

Addition of HCl, HBr, HI Markovnikov regiochemistry occurs, with adding to the less highly substituted alkene carbon and halogen adding to the more highly substituted carbon.

<p>Addition of HCl, HBr, HI Markovnikov regiochemistry occurs, with adding to the less highly substituted alkene carbon and halogen adding to the more highly substituted carbon.</p>
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2

addition reactions of alkenes (Cl2, Br2)

Anti addition is observed through a halonium ion intermediate.

<p>Anti addition is observed through a halonium ion intermediate.</p>
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3

addition reactions of alkenes (halohydrin formation)

Markovnikov regiochemistry and anti stereochemistry occur.

<p>Markovnikov regiochemistry and anti stereochemistry occur.</p>
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4

addition reactions of alkenes (oxymercuration-demercuration)

Markovnikov regiochemistry occurs.

<p>Markovnikov regiochemistry occurs.</p>
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5

addition reactions of alkenes (hydroboration-oxidation)

Non-Markovnikov syn addition occurs.

<p>Non-Markovnikov syn addition occurs.</p>
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addition reactions of alkenes (Catalytic hydrogenation)

Syn addition occurs.

<p>Syn addition occurs.</p>
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7

addition reactions of alkenes (epoxidation)

with a peroxyacid; Syn addition occurs

<p>with a peroxyacid; Syn addition occurs</p>
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8

addition reactions of alkenes (Hydroxylation with OsO4)

Syn addition occurs

<p>Syn addition occurs</p>
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9

addition reactions of alkenes (Addition of carbenes to yield cyclopropanes: Dichlorocarbene addition)

Dichlorocarbene addition

<p>Dichlorocarbene addition</p>
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10

Simmons-Smith reaction

knowt flashcard image
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Hydroxylation by acid-catalyzed epoxide hydrolysis

Anti stereochemistry occurs

<p>Anti stereochemistry occurs</p>
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Oxidative cleavage of alkenes (ozone, zince)

Reaction with ozone followed by zinc in acetic acid

<p>Reaction with ozone followed by zinc in acetic acid</p>
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Oxidative cleavage of alkenes (KMnO4)

Reaction with KMnO4 in acidic solution

<p>Reaction with KMnO4 in acidic solution</p>
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Cleavage of 1,2-diols

Cleavage of 1,2-diols

<p>Cleavage of 1,2-diols</p>
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dehydrohalogenation

alkyl halide + strong base

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dehydration

alcohol + strong acid

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halogenation

add Br or Cl

→ gives anti sterochemitry

<p>add Br or Cl<br><br>→ gives anti sterochemitry</p>
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halohydrins

alkene + HOX

→ DMSO or NBS solvent

<p>alkene + HOX<br><br>→ DMSO or NBS solvent</p>
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hydration

water + alkene = alcohol

→ need high temps

<p>water + alkene = alcohol<br><br>→ need high temps</p>
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oxymercuration-demercuration

alkene + Hg(OAc)2 = alcohol

→ follows Markovnikov rule

<p>alkene + Hg(OAc)2 = alcohol<br><br>→ follows Markovnikov rule</p>
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hydrobromination

alkene + BH3

→ non Markovnikov

<p>alkene + BH3<br><br>→ non Markovnikov</p>
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hydrogenated

alkene + H2 + metal surface = saturated alkane

<p>alkene + H2 + metal surface = saturated alkane</p>
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epoxide reaction

halohydrin + base = epoxide + HX

→ makes a ring

<p>halohydrin + base = epoxide + HX<br><br>→ makes a ring</p>
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hydrolysis

epoxide + water = glycol

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epoxycycloalkane and acid

epoxycycloalkane + acid + water = trans-1,2-diol

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epoxycycloalkane and OsO4

epoxycycloalkane + OsO4 = cis-1,2, diol

<p>epoxycycloalkane + OsO4 = cis-1,2, diol</p>
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ozone + tetra substituted double bond =

keytone + keytone

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ozone + tri substituted double bond =

keytone + alcohol

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disubstituted double bond

aldehyde + aldehyde

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30

periodic acid reactions

adds a carboxyl group

<p>adds a carboxyl group</p>
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31

carbene reaction

forms a cycloalkane

<p>forms a cycloalkane</p>
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32

Simmons-Smith Reaction

the reaction of an alkene with CH2I2 and Zn-Cu to yield cyclopropane

<p>the reaction of an alkene with CH2I2 and Zn-Cu to yield cyclopropane</p>
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