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22 Terms

1

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<p>Combustion of Alkanes</p>

Combustion of Alkanes

No heat, no reaction

<p>No heat, no reaction</p>

2

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<p>Epoxidation of Alkenes</p>

Epoxidation of Alkenes

mCPBA = m-chloroperoxybenzoic

<p>mCPBA = m-chloroperoxybenzoic</p>

3

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<p>Hydroxylation</p>

Hydroxylation

Mild oxidation

Syn addition

Variations:

Step 2. NaHSO4, H2O

or

Step 2. N-methylmorpholine oxide (NMO)

<p>Mild oxidation</p><p>Syn addition</p><p></p><p><strong>Variations:</strong></p><p>Step 2. NaHSO4, H2O</p><p>or</p><p>Step 2. N-methylmorpholine oxide (NMO)</p>

4

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<p>Oxydative Cleavage</p>

Oxydative Cleavage

Cis diols only!

Aldehyde product

Mild oxidative cleavage

<p>Cis diols only!</p><p>Aldehyde product</p><p>Mild oxidative cleavage</p>

5

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<p>Ozonolysis</p>

Ozonolysis

Mild Oxidation

Break double bond

End groups stay the same

May lead to mixtures with asymmetric alkenes

<p>Mild Oxidation</p><p>Break double bond</p><p>End groups stay the same</p><p>May lead to mixtures with asymmetric alkenes</p>

6

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<p>Permanganate Oxidation</p>

Permanganate Oxidation

Vigorous Oxidation

Complete oxidation, does not stop at the aldehyde

<p>Vigorous Oxidation</p><p>Complete oxidation, does not stop at the aldehyde</p>

7

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<p>Hydrogenation</p>

Hydrogenation

Reduction to alkane

Syn addition of H₂ (or D₂)

<p>Reduction to alkane</p><p>Syn addition of H<sub>2</sub> (or D<sub>2</sub>)</p>

8

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<p>Addition of Carbenes</p>

Addition of Carbenes

Highly reactive

Unfilled octet

Formal charge on carbene carbon = 0

<p>Highly reactive</p><p>Unfilled octet</p><p>Formal charge on carbene carbon = 0</p>

9

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<p>Generation of Carbenes (1)</p>

Generation of Carbenes (1)

Dichlorocarbene only

<p>Dichlorocarbene only</p>

10

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<p>Generation of Carbenes (2)</p>

Generation of Carbenes (2)

R = H, alkyl

<p>R = H, alkyl</p>

11

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<p>Simmons-Smith Cyclopropanation (1)</p>

Simmons-Smith Cyclopropanation (1)

knowt flashcard image

12

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<p>Simmons-Smith Cyclopropanation (2)</p>

Simmons-Smith Cyclopropanation (2)

knowt flashcard image

13

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<p>Radical Addition of HBr</p>

Radical Addition of HBr

Anti-Markovnikov orientation

Only HBr (or DBr), no HI or HCl

Radical mechanism

<p>Anti-Markovnikov orientation</p><p>Only HBr (or DBr), no HI or HCl</p><p>Radical mechanism</p>

14

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<p>Allylic Bromination</p>

Allylic Bromination

Radical mechanism via resonance stabilized allyl (or benzyl) radical

<p>Radical mechanism via resonance stabilized allyl (or benzyl) radical</p>

15

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<p>Benzylic Bromination</p>

Benzylic Bromination

Radical mechanism via resonance stabilized allyl (or benzyl) radical

<p>Radical mechanism via resonance stabilized allyl (or benzyl) radical</p>

16

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<p>Syntehsis of Alkenes (1)</p>

Syntehsis of Alkenes (1)

Elimination of HBr

More substituted C=C (Saytzeff orientation)

<p>Elimination of HBr</p><p>More substituted C=C (Saytzeff orientation)</p>

17

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<p>Synthesis of Alkenes (2)</p>

Synthesis of Alkenes (2)

Elimination of H2O

Needs heat

<p>Elimination of H2O</p><p>Needs heat</p>

18

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<p>Full Reduction</p>

Full Reduction

Also with D2

Other catalysts: Ni, Pt, Pd, PtO

Full reduction to alkane

No reaction without catalyst

<p>Also with D2</p><p>Other catalysts: Ni, Pt, Pd, PtO</p><p>Full reduction to alkane</p><p>No reaction without catalyst</p>

19

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<p>Partial Reduction</p>

Partial Reduction

Lindlar’s catalyst

Syn - addition (Z isomer)

D2 also

<p>Lindlar’s catalyst</p><p>Syn - addition (Z isomer)</p><p>D2 also</p>

20

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<p>Dissolving Metal Reduction</p>

Dissolving Metal Reduction

Anti – addition

Also ND3 instead of NH₃

<p>Anti – addition</p><p>Also ND3 instead of NH<sub>3</sub></p>

21

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<p>Oxidative Cleavage (1)</p>

Oxidative Cleavage (1)

May lead to mixtures if asymmetric alkyne is used

Break alkyne to form carboxylic acids

<p>May lead to mixtures if asymmetric alkyne is used</p><p>Break alkyne to form carboxylic acids</p>

22

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<p>Oxidative Cleavage (2)</p>

Oxidative Cleavage (2)

One product + CO₂ (g)

<p>One product + CO<sub>2</sub> (g)</p>