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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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Hydroxyapatite: catalyst for a one-pot pentose formation.

K Usami1, A Okamoto

  • 1Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan. okamoto@chembio.t.u-tokyo.ac.jp.

Organic & Biomolecular Chemistry
|September 28, 2017
PubMed
Summary
This summary is machine-generated.

Hydroxyapatite (HAp) enables one-pot synthesis of ribose from simple carbon sources in hot water. This catalytic process, without strict conditions, offers insights into prebiotic nucleic acid formation.

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Area of Science:

  • Chemistry
  • Biochemistry
  • Astrobiology

Background:

  • The formose reaction pathway offers a route to pentoses from C1 and C2 carbon sources.
  • Preferential, one-pot synthesis of ribose under uncontrolled conditions remains a challenge.

Purpose of the Study:

  • To investigate a one-pot method for pentose formation.
  • To analyze the products and reaction mechanism for preferential ribose generation.

Main Methods:

  • Utilized hydroxyapatite (HAp) as a catalyst in a one-pot reaction.
  • Employed 1H-NMR and mass spectrometry for product and mechanism analysis.
  • Conducted reactions in hot water without stringent pH or condition control.

Main Results:

  • Hydroxyapatite (HAp) facilitated continuous cross-aldol reactions and Lobry de Bruyn-van Ekenstein transformations.
  • Successfully yielded ribose from formaldehyde and glycolaldehyde.
  • Demonstrated efficient ribose production in a single pot under simple, hot water conditions.

Conclusions:

  • HAp acts as an effective catalyst for one-pot ribose synthesis from simple aldehydes.
  • The simplicity of the HAp-catalyzed reaction suggests a plausible mechanism for prebiotic ribose formation.
  • This pathway may explain the incorporation of pentose backbones into nucleic acids in the early Earth.