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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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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





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



+

+

-

-

d

d

d

d

Fig. 7-4, p. 225



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)


epep !


Alkenes alkynes15
Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • C. Alkyne alkylation



Alkenes alkynes16
Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • D. Carbene addition




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)



Alkenes alkynes19
Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • E. Oxidations

    • 1. epoxidation

  • ii. via halohydrins


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




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



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





Alkenes alkynes28
Alkenes & Alkynes

  • Reactions of alkenes & alkynes

  • F. Conjugated Dienes

    • 1. Addition of HX



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


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



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)



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