Ketones and aldehydes
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Ketones and Aldehydes. Properties Nomenclature Preparation Reactions Synthesis. Carbonyl Functional Groups. Large Dipole Controls Properties and Reactivity. Boiling Points Dipole-Dipole Interactions. Adrogenic/Anabolic Steroids. Anabolic Steroids. IUPAC Nomenclature Ketones.

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Ketones and aldehydes

Ketones and Aldehydes

Properties

Nomenclature

Preparation

Reactions

Synthesis




Boiling points dipole dipole interactions
Boiling PointsDipole-Dipole Interactions







Preparation of ketones and aldehydes
Preparation of Ketones and Aldehydes

  • Friedel-Crafts Acylation(ketones)

  • Gatterman-Koch Formylation (aldehydes)

  • Hydration of Alkynes(ketones with oxymercuration, aldehydes with hydroboration)

  • Ozonolysis of Alkenes (aldehydesand ketonesdepending on substitution)

  • 1,3-Dithiane alkylations(aldehydesand ketones)

  • Reduction of acids, acid chlorides and nitriles

  • Gilman Reaction (ketones)



Isoflavones highly sought after natural products
IsoflavonesHighly Sought After Natural Products


Acylation occurs ortho to oh
Acylation occurs ortho to OH




Hydroboration hydration anti markovnikov
Hydroboration HydrationAnti-Markovnikov


Ozonolysis alkene cleavage
OzonolysisAlkene Cleavage


Gilman reagent with acid chlorides
Gilman Reagent with Acid Chlorides


Dibah d i i so b utyl a luminum h ydride
DIBAHDiisobutyl Aluminum Hydride


















Enamine mechanism same as imine mech until last step
Enamine Mechanism(same as imine mech. until last step)


Wittig reaction c o into c c
Wittig Reaction:C=O into C=C








Conjugate addition to a b unsaturated c o groups
Conjugate Addition toa,b-Unsaturated C=O groups


1 2 vs 1 4 addition
1,2- vs.1,4-Addition





Mcad deficiency a genetic disease
MCAD Deficiency, a Genetic Disease

  • Children with any of these enzyme deficiencies have a significant risk (20%) of death during the first, clinical episode of hypoglycemia (low blood glucose).

  • Those patients affected show episodes of acute, life-threatening attacks that are symptomatically consistent with Reye’s Syndrome and sometimes misdiagnosed as S.I.D.S.

  • The most common of these in-born errors is MCAD Deficiency. (Medium ChainAcyl-CoADehydrogenase)

  • ~1/50 Caucasians carry the gene.


Mcad enzyme
MCAD Enzyme

  • (MCAD) is one of the enzymes involved in mitochondrial fatty acid b-oxidation, which fuels hepatic ketogenesis, a major source of energy once hepatic glycogen stores become depleted during prolonged fasting and periods of higher energy demands.

  • Typically, a previously healthy child with MCAD deficiency presents with hypoketotic hypoglycemia, vomiting, liver dysfunction, skeletal muscle weakness and lethargy triggered by a common illness. On average, this occurs between 3 and 24 months of age.


Ackee fruit bligia sapida from jamaica
Ackee Fruit (BligiaSapida) from Jamaica

Ingestion of the unripe seeds from the fruit of the Jamaican Ackee tree causes a disruption of the dehydrogenase enzymes needed to metabolize fatty acids. This “vomiting sickness” is a result of the enzyme inhibitor Hypoglycin A.


R mcpa is the toxic metabolite of hypoglycin a
(R)(-) MCPA is the Toxic Metabolite of Hypoglycin-A



Wittig approach to s mcpa start with r epichlorohydrin s n 2 on 1 o alkyl chloride
Wittig Approach to (S)(+)-MCPAStart with (R)(-) EpichlorohydrinSN2 on 1o Alkyl Chloride?


Wittig sequence affords s methylenecyclopropyl methanol
Wittig Sequence Affords (S) (Methylenecyclopropyl)methanol



Approach to r mcpa same wittig approach with ylide opening the epoxide first
Approach to (R)-(+)-MCPA Same Wittig Approach with YlideOpening the Epoxide First?


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