Exam II Reagents + Common IUPAC structures

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Ch. 16, Ch. 17, Ch. 18, Ch. 19

31 Terms

1
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Ch. 17 Reactions at benzylic position: oxidation reagents

Converts an alkyl group into a carboxylic acid (provided it has enough Hs)


Na2Cr2O7, H2SO4, H2O

OR

1) KMnO4, H2O, heat

2) H3O+

<p>Converts an alkyl group into a carboxylic acid (provided it has enough Hs)</p><p></p><p>Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>, H<sub>2</sub>SO<sub>4</sub>, H<sub>2</sub>O</p><p>OR</p><p>1) KMnO<sub>4</sub>, H<sub>2</sub>O, heat</p><p>2) H<sub>3</sub>O+</p>
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Ch. 17 SN2

Tertiary Br —> OH uses a weak nuc (H2O)

Primary Br —> OH uses a strong nuc (-OH)

<p>Tertiary Br —&gt; OH uses a weak nuc (H<sub>2</sub>O)</p><p>Primary Br —&gt; OH uses a strong nuc (-OH)</p>
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Ch. 17 Free radical bromination

NBS, heat

<p>NBS, heat</p>
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Ch. 17 Elimination rxns

Hydride shift E1: use concentrated H2SO4

forms carbocation

<p>Hydride shift E1: use concentrated H<sub>2</sub>SO<sub>4</sub></p><p>forms carbocation</p>
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Ch. 17 Birch Reduction

conjugated benzene to diene

Na, CH3OH, NH3 (l)

<p>conjugated benzene to diene</p><p>Na, CH<sub>3</sub>OH, NH<sub>3</sub> (l)</p>
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Ch. 18 Halogenation

X2

Al or FeX3

<p>X<sub>2</sub></p><p>Al or FeX<sub>3</sub></p>
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Ch. 18 Nitration

HNO3, H2SO4

<p>HNO<sub>3</sub>, H<sub>2</sub>SO<sub>4</sub></p>
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Ch. 18 Sulfonation + reverse

Fuming H2SO4

Reverse: dilute H2SO4

<p>Fuming H<sub>2</sub>SO<sub>4</sub></p><p>Reverse: dilute H<sub>2</sub>SO<sub>4</sub></p>
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Ch. 18 FC alkylation

RX

AlX3

<p>RX</p><p>AlX<sub>3</sub></p>
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Ch. 18 FC acylation

x-(C=O)R

1) AlX3

2) H2O

<p>x-(C=O)R</p><p>1) AlX<sub>3</sub></p><p>2) H<sub>2</sub>O</p>
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Ch. 18 Nitro group reduction

1) Fe or Zn, HCl

2) NaOH

<p>1) Fe or Zn, HCl</p><p>2) NaOH</p>
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Ch. 18 Clemmenson reduction

ZnHg, HCl, heat

<p>ZnHg, HCl, heat</p>
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Ch. 18 NAS/SnAR

1) NaOH, 70 degrees C

2) H3O+

<p>1) NaOH, 70 degrees C</p><p>2) H3O+</p>
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Ch. 18 Elimination addition

1) NaOH, 350 degrees C

2) H3O+

or

1) NaNH2, NH3 (l)

2) H3O+

<p>1) NaOH, 350 degrees C</p><p>2) H3O+</p><p>or</p><p>1) NaNH2, NH<sub>3</sub> (l)</p><p>2) H<sub>3</sub>O+</p>
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Ch. 19 Hydrate formation

[H+], H2O

<p>[H+], H<sub>2</sub>O</p>
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Ch. 19 Acetal formation

[H+], ROH, -H2O

<p>[H+], ROH, -H<sub>2</sub>O</p>
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Ch. 19 Cyclic acetal formation

some diol

[H+], -H2O

<p>some diol</p><p>[H+], -H<sub>2</sub>O</p>
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Ch. 19 Imine formation

[H+]

RNH2

-H2O

<p>[H+]</p><p>RNH<sub>2</sub></p><p>-H<sub>2</sub>O</p>
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Ch. 19 Enamine formation

[H+]

R2NH

-H2O

<p>[H+]</p><p>R<sub>2</sub>NH</p><p>-H<sub>2</sub>O</p>
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Ch. 19 hydrazone formation

[H+]

NH2NH2

-H2O

<p>[H+]</p><p>NH<sub>2</sub>NH<sub>2</sub></p><p>-H<sub>2</sub>O</p>
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Ch. 19 (mechanism not on exam) Wolff-Kishner Reduction

formation of hydrazone, then

NaOH or KOH, H2O, heat

<p>formation of hydrazone, then </p><p>NaOH or KOH, H<sub>2</sub>O, heat</p>
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hydrolysis reagents

[H+] H2O

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<p></p>


thiophene

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furan

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pyridine

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pyrrole

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formaldehyde

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<p></p>


acetaldehyde

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cyclohexanecarbaldehyde

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<p></p>


acetone

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benzophenone