Organic Chemistry 1 Exam 3 Reagents

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Last updated 4:44 PM on 4/21/26
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27 Terms

1
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H2, Pd/c

alkene to alkane

syn addition

<p>alkene to alkane</p><p>syn addition</p>
2
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H2, Pd/c

Alkyne to alkane

syn addition

<p>Alkyne to alkane</p><p>syn addition</p>
3
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H2SO4, H2O

Alkene to alcohol

Markovnikov Addition

<p>Alkene to alcohol</p><p>Markovnikov Addition</p>
4
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H2SO4, H2O

Alkyne to enol to aldehyde/ketone (Tautomerization)

Markovnikov addition

<p>Alkyne to enol to aldehyde/ketone (Tautomerization)</p><p>Markovnikov addition</p>
5
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HX

Electrophilic Addition (Acids)

Alkene to Alkane

Markovnikov addition

<p>Electrophilic Addition (Acids)</p><p>Alkene to Alkane</p><p>Markovnikov addition</p>
6
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HX

Electrophilic Addition (Acids)

Alkyne to Alkane (2 equiv)

Markovnikov addition

<p>Electrophilic Addition (Acids)</p><p>Alkyne to Alkane (2 equiv)</p><p>Markovnikov addition</p>
7
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Br2, hv

Alkene to Alkane

Bromination

Markovnikov Addition

<p>Alkene to Alkane</p><p>Bromination</p><p>Markovnikov Addition</p>
8
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Br2,hv

Alkyne to Alkane (2 equiv.)

Markovnikov addition

2 Br on the same carbon

<p>Alkyne to Alkane (2 equiv.)</p><p>Markovnikov addition</p><p>2 Br on the same carbon</p>
9
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Br2, CCl4

Electrophilic Addition (dihalides)

Alkene to Alkane

Bromonium formation

Anti-Addition of 2 Br

<p>Electrophilic Addition (dihalides)</p><p>Alkene to Alkane</p><p>Bromonium formation</p><p>Anti-Addition of 2 Br</p>
10
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Br2, CCl4

Electrophilic Addition (dihalides)

Alkyne to Alkane (2 equiv. )

Anti-Addition bromination 4 Br total, 2 Br on each carbon

<p>Electrophilic Addition (dihalides)</p><p>Alkyne to Alkane (2 equiv. )</p><p>Anti-Addition bromination 4 Br total, 2 Br on each carbon</p>
11
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Br2, H2O

Electrophilic Addition (dihalides)

Alkene to alcohol

Anti-Addition of an alcohol and a Br

<p>Electrophilic Addition (dihalides)</p><p>Alkene to alcohol</p><p>Anti-Addition of an alcohol and a Br</p>
12
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Br2, H2O

Electrophilic Addition (dihalides)

Alkyne to enol to aldehyde/ketone (Tautomerization)

<p>Electrophilic Addition (dihalides)</p><p>Alkyne to enol to aldehyde/ketone (Tautomerization)</p>
13
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1) Hg(OAc)2, H2O

2) NaBH4

Oxymercuration

Alkene to alcohol

Markovnikov Addition of alcohol

<p>Oxymercuration</p><p>Alkene to alcohol</p><p>Markovnikov Addition of alcohol</p>
14
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1) Hg(OAc)2, H2O

2) NaBH4

Oxymercuration

Alkyne to enol to aldehyde/ketone

Markovnikov addition

<p>Oxymercuration</p><p>Alkyne to enol to aldehyde/ketone</p><p>Markovnikov addition</p>
15
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1) BH3, THF

2) H2O2, NaOH

Hydroboration/ Oxidation

Alkene to alcohol

Anti- Markovnikov addition of an alcohol

<p>Hydroboration/ Oxidation</p><p>Alkene to alcohol</p><p>Anti- Markovnikov addition of an alcohol</p>
16
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1) BH3, THF

2) H2O2, NaOH

Hydroboration/ Oxidation

Alkyne to enol to aldehyde/ketone

Anti-Markovnikov addition

<p>Hydroboration/ Oxidation</p><p>Alkyne to enol to aldehyde/ketone</p><p>Anti-Markovnikov addition</p>
17
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1) HBr

2)tBuO-OtBu

Radical Halogenation

Alkene to Alkane

Anti-Markovnikov addition of a Br

<p>Radical Halogenation</p><p>Alkene to Alkane</p><p>Anti-Markovnikov addition of a Br</p>
18
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1) HBr (excess)

2)tBuO-OtBu

Radical Halogenation

Alkyne to Alkane

Anti-Markovnikov addition of a Br

<p>Radical Halogenation</p><p>Alkyne to Alkane</p><p>Anti-Markovnikov addition of a Br</p>
19
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meta-Chloroperoxybenzoic acid (mCPBA)

Epoxidation

Alkene to epoxide

<p>Epoxidation</p><p>Alkene to epoxide</p>
20
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1) OsO4

2) H2S/ H2O

Dihydroxylation

Alkene to 2 alcohols

Syn addition of 2 OH

<p>Dihydroxylation</p><p>Alkene to 2 alcohols</p><p>Syn addition of 2 OH</p>
21
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1) O3

2) Zn/ S(CH3)2

Ozonolysis

Alkene to 2 carbonyls (Aldehydes)

<p>Ozonolysis</p><p>Alkene to 2 carbonyls (Aldehydes)</p>
22
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1) NaNh2

2) H3O work up

Alkane to Alkyne

Double elimination (E2 * 2)

<p>Alkane to Alkyne</p><p>Double elimination (E2 * 2)</p>
23
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1) H2, Pd/c, quinoline/ Pb(OAc)2

Lindlar's Catalyst

Semi - hydrogenation of Alkyne to form a cis - Alkene

<p>Lindlar's Catalyst</p><p>Semi - hydrogenation of Alkyne to form a cis - Alkene</p>
24
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1) Na (excess)

2) NH3

Alkyne to Alkene

Trans Alkene formation

<p>Alkyne to Alkene</p><p>Trans Alkene formation</p>
25
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Li (Bulk) /Base

Removes H from Alkyne making a negative C used as a nucleophile

<p>Removes H from Alkyne making a negative C used as a nucleophile</p>
26
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Br2, CH3OH

Alkene to Alkane

Bromination formation

Trans addition of Br and OCH3

<p>Alkene to Alkane</p><p>Bromination formation</p><p>Trans addition of Br and OCH3</p>
27
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Br2, CH3OH

Alkyne to Alkane

Bromination formation

Anti-Addition of Br and OCH3