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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
slide14
+

+

-

-

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)
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
slide34
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

slide55
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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