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p. 251. Alkenes & Alkynes. Prepapration of alkenes 1. Dehydrohalogenation 2. Dehydration. Alkenes & Alkynes. Reactions of alkenes & alkynes A. Electrophilic Additions Hydrohalogenation i. alkenes ii. alkynes 2. Halogenation i. alkenes ii. alkynes Halohydrins i. alkenes

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P 251

p. 251


Alkenes alkynes

Alkenes & Alkynes

  • Prepapration of alkenes

    • 1. Dehydrohalogenation

    • 2. Dehydration


Alkenes alkynes1

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • Hydrohalogenation

  • i. alkenes

  • ii. alkynes

    • 2. Halogenation

  • i. alkenes

  • ii. alkynes

    • Halohydrins

  • i. alkenes

  • ii. alkynes

    • 4. Hydration

  • i. alkenes

  • ii. alkynes


Alkenes alkynes2

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • Hydrohalogenation

  • i. alkenes

  • ii. alkynes


Electrophilic addition of br 2 to an alkene

Electrophilic addition of Br2 to an alkene


P 251

p. 217


P 251

p. 218


Alkenes alkynes3

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • 2. Halogenation

  • i. alkenes (working backwards)


Alkenes alkynes4

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • Halohydrins

  • i. alkenes


Alkenes alkynes5

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • Halohydrins

  • ii. alkynes


Alkenes alkynes6

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • 4. Hydration

  • i. alkenes

  • a. acid catalyzed


Alkenes alkynes7

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • 4. Hydration

  • i. alkenes

  • a. hydroboration & oxidation


P 251

p. 223


P 251

+

+

-

-

d

d

d

d

Fig. 7-4, p. 225


P 251

Jmol


Alkenes alkynes8

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • 4. Hydration

  • i. alkynes

  • a. acid catalyzed


Alkenes alkynes9

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • 4. Hydration

  • i. alkynes

  • b. oxymercuration


Alkenes alkynes10

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • A. Electrophilic Additions

    • 4. Hydration

  • i. alkynes

  • a. hydroboration & oxidation


Alkenes alkynes11

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • B. Reductions

    • 1. Alkenes

  • i. Catalytic hydrogenation


Alkenes alkynes12

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • B. Reductions

    • 1. Alkynes

  • i. Catalytic hydrogenation

  • a. Complete reduction


Alkenes alkynes13

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • B. Reductions

    • 1. Alkynes

  • i. Catalytic hydrogenation

  • b. Lindlar’s catalyst (partial reduction)


Alkenes alkynes14

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • C. Reductions

    • 1. Alkynes

  • ii. Dissolving metal reduction (partial reduction)


P 251

epep !


Alkenes alkynes15

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • C. Alkyne alkylation


P 251

Fig. 8-19, p. 292


Alkenes alkynes16

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • D. Carbene addition


P 251

Fig. 7-6, p. 228


P 251

Carbenes


Alkenes alkynes17

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • Introduction


Alkenes alkynes18

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 1. epoxidation

  • Peracids (RCO3H)


P 251

Epoxide formation through reaction of peracids


Alkenes alkynes19

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 1. epoxidation

  • ii. via halohydrins


P 251

The Nobel Prize in Chemistry 2001

"for their work on chirally catalysed hydrogenation reactions"

"for his work on chirally catalysed oxidation reactions"

William S. Knowles

Ryoji Noyori

K. Barry Sharpless


Thalidomide

Thalidomide

  • Racemic thalidomide prescribed for morning sickness (1956 – 1961)

  • (R)-enantiomer is an antiemetic

  • (S)-enantiomer is a teratogen


Sharpless epoxidation

Sharpless epoxidation

(CH3)3COOH


Knowles asymmetric reduction

Knowles Asymmetric Reduction


Alkenes alkynes20

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 2. dihydroxylation

  • i. osmium tetraoxide


Alkenes alkynes21

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 2. dihydroxylation

  • ii. from epoxides


Alkenes alkynes22

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 2. Dihydroxylation

    • Application : Synthesis


Alkenes alkynes23

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 3. oxidative cleavage

  • i. ozonolysis


P 251

p. 237


Alkenes alkynes24

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 3. oxidative cleavage

  • i. ozonolysis


Alkenes alkynes25

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 3. oxidative cleavage

  • ii. permanganate


Alkenes alkynes26

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 3. oxidative cleavage

  • iii. from diols


Alkenes alkynes27

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • Introduction


P 251

Fig. 8-12, p. 281


P 251

Fig. 8-13, p. 282


P 251

Fig. 8-14, p. 282


Alkenes alkynes28

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 1. Addition of HX


Reaction energy diagram for addition of hbr to butadiene

Reaction energy diagram for addition of HBr to butadiene


Alkenes alkynes29

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Introduction

    • a. the overall reaction

    • b. history

    • c. nature of the diene and dienophile

    • d. the molecular orbital picture

    • e. conformation of the diene


Alkenes alkynes30

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Introduction

    • a. the overall reaction


Alkenes alkynes31

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Introduction

    • b. history

Albrecht reaction

Liebigs1906, 348, 31.

Staudinger, H.; Bruson, H. A.

Liebigs1926 , 446 , 97.

Diels, O.; Alder, K.

Liebigs. 1928, 460, 98.

Nobel Prize 1950


P 251

Otto Paul Hermann Diels

Kurt Alder

The Nobel Prize in Chemistry 1950

"for their discovery and development of the diene synthesis "


Alkenes alkynes32

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Introduction

    • c. nature of the diene and dienophile


P 251

p. 286


Alkenes alkynes33

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Introduction

    • d. the molecular orbital picture


Alkenes alkynes34

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Introduction

    • e. the diene conformation


Alkenes alkynes35

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Stereochemistry (Alder’sEndo Rule)


Alkenes alkynes36

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Regiochemistry (The Ortho Rule)


Alkenes alkynes37

Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 2. The Diels-Alder reaction

    • Regiochemistry (The Para Rule)


P 251

Fig. 8-17, p. 287


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