Exam 3 CHEM 241

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Term: Reagent, Definition: Action

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29 Terms

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Alkenes Addition Map

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Alkynes Addition Map

<p></p>
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Radical Steps

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Cl2/hv

same use as Br2/v except installation of Cl at the most substituted position

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Br2/hv

installation of Br (replacing a hydrogen atom) at the most substituted position

<p>installation of Br (replacing a hydrogen atom) at the most substituted position</p>
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HBr/ROOR

Alkene undergoes anti-Markovnikov addition of H and Br

<p>Alkene undergoes anti-Markovnikov addition of H and Br</p>
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NBS/hv

install a bromine atom at the allylic position of an alkene

<p><span>install a bromine atom at the allylic position of an alkene</span></p>
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<p>HX</p>

HX

Treating an alkene with this reagent gives Markovnikov addition of H and X across the alkene.

(Hydrohalogenation)

<p>Treating an alkene with this reagent gives Markovnikov addition of H and X across the alkene.</p><p>(Hydrohalogenation)</p>
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H3O+

Treating an alkene with this reagent gives Markovnikov addition of H and OH across the alkene.

(Acid-cat. hydration)

<p>Treating an alkene with this reagent gives Markovnikov addition of H and OH across the alkene.</p><p>(Acid-cat. hydration)</p>
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<p>1) Hg(OAc)2, H2O (H2O can be replaced with a nucleophile)</p><p>2) NaBH4</p>

1) Hg(OAc)2, H2O (H2O can be replaced with a nucleophile)

2) NaBH4

Treating an alkene with these reagents gives Markovnikov addition of H and OH across the alkene, without any carbocation rearrangements.

(Oxymercuration-demercuration)

<p>Treating an alkene with these reagents gives Markovnikov addition of H and OH across the alkene, without any carbocation rearrangements.</p><p>(Oxymercuration-demercuration)</p>
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<p>1) BH3 • THF</p><p>2) H2O2, NaOH</p>

1) BH3 • THF

2) H2O2, NaOH

Treating an alkene with these reagents gives anti-Markovnikov addition of H and OH across the alkene. The reaction proceeds exclusively via a syn addition.

(hydroboration-oxidation)

<p>Treating an alkene with these reagents gives anti-Markovnikov addition of H and OH across the alkene. The reaction proceeds exclusively via a syn addition.</p><p>(hydroboration-oxidation)</p>
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<p>H2, Pt</p>

H2, Pt

Treating an alkene with these reagents gives syn addition of H and H across the alkene.

(Hydrogenation)

<p>Treating an alkene with these reagents gives syn addition of H and H across the alkene.</p><p>(Hydrogenation)</p>
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Br2

Treating an alkene with this reagent gives anti addition of Br and Br across the alkene.

(bromination/halogenation)

<p>Treating an alkene with this reagent gives anti addition of Br and Br across the alkene.</p><p>(bromination/halogenation)</p>
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<p>Br2, H2O</p>

Br2, H2O

Treating an alkene with these reagents gives anti addition of Br and OH across the alkene, with the OH group being installed at the more substituted position.

(Halohydrin formation)

<p>Treating an alkene with these reagents gives anti addition of Br and OH across the alkene, with the OH group being installed at the more substituted position.</p><p>(Halohydrin formation)</p>
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<p>1) RCO3H</p><p>2) H3O+</p>

1) RCO3H

2) H3O+

Treating an alkene with a peroxy acid (RCO3H) converts the alkene into an epoxide, which is then opened upon treatment with aqueous acid to give a trans-diol.

(anti-dihydroxylation)

<p>Treating an alkene with a peroxy acid (RCO3H) converts the alkene into an epoxide, which is then opened upon treatment with aqueous acid to give a trans-diol.</p><p>(anti-dihydroxylation)</p>
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<p>KMnO4, NaOH, cold or </p><p>1) OsO4</p><p>2) NaHSO3, H2O</p>

KMnO4, NaOH, cold or

1) OsO4

2) NaHSO3, H2O

Treating an alkene with these reagents gives syn addition of OH and OH across the alkene.

(syn-dihydroxylation)

<p>Treating an alkene with these reagents gives syn addition of OH and OH across the alkene.</p><p>(syn-dihydroxylation)</p>
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1) O3

2) DMS

Ozonolysis of an alkene causes cleavage of the C=C bond, giving two compounds, each of which possesses a C=O bond.

(ozonolysis)

<p>Ozonolysis of an alkene causes cleavage of the C=C bond, giving two compounds, each of which possesses a C=O bond.</p><p>(ozonolysis)</p>
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<p>1) excess NaNH2</p><p>2) H2O</p>

1) excess NaNH2

2) H2O

When treated with these reagents, a vicinal or geminal dibromide is converted to an alkyne.

(elimination)

<p>When treated with these reagents, a vicinal or geminal dibromide is converted to an alkyne.</p><p>(elimination)</p>
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1) R2BH

2) H2O2, NaOH

When treated with these reagents, a terminal alkyne undergoes anti-Markovnikov addition of H and OH to give an enol, which quickly tautomerizes to give an aldehyde.

(Hydroboration-oxidation)

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1) O3

2) H2O

When treated with these reagents, an alkyne undergoes oxidative cleavage of the C≡C bond. Internal alkynes are converted into two carboxylic acids, while terminal alkynes are converted into a carboxylic acid and carbon dioxide.

(ozonolysis)

<p>When treated with these reagents, an alkyne undergoes oxidative cleavage of the C≡C bond. Internal alkynes are converted into two carboxylic acids, while terminal alkynes are converted into a carboxylic acid and carbon dioxide.</p><p>(ozonolysis)</p>
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<p>H2, Lindlar’s catalyst</p>

H2, Lindlar’s catalyst

When treated with these reagents, an alkyne is converted to a cis alkene.

(hydrogenation)

<p>When treated with these reagents, an alkyne is converted to a cis alkene.</p><p>(hydrogenation)</p>
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<p>Na, NH3 (l)</p>

Na, NH3 (l)

When treated with these reagents, an internal alkyne is converted to a trans alkene.

(dissolving metal reaction)

<p>When treated with these reagents, an internal alkyne is converted to a trans alkene.</p><p>(dissolving metal reaction)</p>
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<p>X2</p>

X2

When treated with this reagent, an alkyne undergoes addition of X and X (excess X2 gives a tetrahalide).

(halogenation)

<p>When treated with this reagent, an alkyne undergoes addition of X and X (excess X2 gives a tetrahalide).</p><p>(halogenation)</p>
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<p>HX</p>

HX

When treated with HX, an alkyne undergoes Markovnikov addition (excess HX gives two addition reactions to afford a geminal dihalide).

(hydrohalogenation)

<p>When treated with HX, an alkyne undergoes Markovnikov addition (excess HX gives two addition reactions to afford a geminal dihalide).</p><p>(hydrohalogenation)</p>
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<p>H2SO4, H2O, HgSO4</p>

H2SO4, H2O, HgSO4

When treated with these reagents, a terminal alkyne undergoes Markovnikov addition of H and OH to give an enol, which quickly tautomerizes to give a ketone.

(Acid-cat. hydration)

<p>When treated with these reagents, a terminal alkyne undergoes Markovnikov addition of H and OH to give an enol, which quickly tautomerizes to give a ketone.</p><p>(Acid-cat. hydration)</p>
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<p>Relationship between H2SO4 and R2BH</p>

Relationship between H2SO4 and R2BH

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<p>Excess vs one equivalent halogenation</p>

Excess vs one equivalent halogenation

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<p>NaNH2/H2O</p>

NaNH2/H2O

adds group before/after triple bond

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<p>Table 11.1</p>

Table 11.1

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