Lecture 4 Vanillin 021010

Lecture 4 Vanillin 021010 - Lab#4ReductionofVanillin O H...

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Lab #4 - Reduction of Vanillin HO O O 4-Hydroxy-3-methoxybenzaldehyde NaBH 4 H 3 O+ workup HO OH O 4-Hydroxy-3-methoxybenzyl alcohol H
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Announcements Great job in lab this week!  Great Crystals!       
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Discussion Topics Natural Products vs. Synthetic Equivalents Vanillin Reduction NMR
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Natural Products Therapeutic agents Flavors Fragrances Natural Feedstocks Fuels Raw materials
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Natural Products Taxol -  Taxus brevifolia
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Flavors and Fragrances Flavors Fragrances O H O H R-Carvone Spearmint Caraway C H 3 OH CH 3 C H 3 H C H 3 OH CH 3 H C H 3 3-R-(+)-Citronellol citronella 3-S-(-)-Citronellol rose
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Natural products Renewable Limited Supply Difficult to grow Environmentally responsible? Cut down forests Harvest marine sponges Natural = Good but at what cost??? Synthetic or Semi-Synthetic Equivalent
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Natural vs. Synthetic Vanilla Natural Grows in South America Bean pods Semi-Synthetic Make it in lab By-product of pulp and paper industry Lignin Binder, dispersant, metal deactivators, emulsifiers http://www.lignin.org OH OMe O H
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Lignin…kind  of http://www.lignin.org/01augdialogue.html OH OMe O H
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Natural vs. Synthetic Vanillin  2500 tons / year $10,275 / kg Comes from the vanilla bean <1% (wt) is vanillin “natural vanilla” - $12.99 / 2oz Semi-Synthetic Equivalent Chemically identical main ingredient Made in the lab “imitation vanilla” - $5.99 / 2oz OH OMe O H
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What is Reduction? Oxidation Adds oxygen  Loses Electrons Loses H Reduction Gains Electrons Loses Oxygen or Halogens Adds Hydrogen  H .  or H :
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Sodium Borohydride – NaBH 4 Reducing agent Chemospecific Hydride Source - H - Nomenclature: Proton = H + Hydrogen = H . NaBH 4 H- + NaBH 3 + breaks down further
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Mechanism of reaction Aldehyde to Alcohol Nucleophilic Attack of Hydride on Carbonyl HO O o H H 3 C H - HO O O - H H 3 C H HO O O H H 3 C H H OH H
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Analytical Techniques Melting Point – Purity IR - Gains and Losses New –OH peak Loss of Aldehyde Carbonyl Different than Ketone Carbonyl Loss of Fermi Doublet O= C-H NMR
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NMR Spectroscopy a charged particle moving in a magnetic field creates  an electric field perpendicular to the magnetic field MRI was developed as an off-shoot of NMR It is really NMR for the body… Nuclei of atoms have a positive charge They also have a certain spin angular momentum.
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This note was uploaded on 06/28/2010 for the course CHEM 258 taught by Professor Taylor during the Spring '10 term at Wesleyan.

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Lecture 4 Vanillin 021010 - Lab#4ReductionofVanillin O H...

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