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    Week 8: Adol Condensation

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    frenchisbomb
    1. The document describes an experiment to perform an aldol condensation reaction between an unknown aldehyde and ketone, identified using IR spectroscopy. 2. The product will be analyzed using melting point, NMR, and IR to determine the structure. 3. A double crossed aldol condensation is expected to occur, forming a doubly conjugated ketone product, which often appears colored due to its conjugated system.

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    Week 8: Adol Condensation

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    frenchisbomb
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    1. The document describes an experiment to perform an aldol condensation reaction between an unknown aldehyde and ketone, identified using IR spectroscopy. 2. The product will be analyzed using melting point, NMR, and IR to determine the structure. 3. A double crossed aldol condensation is expected to occur, forming a doubly conjugated ketone product, which often appears colored due to its conjugated system.

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    1. The document describes an experiment to perform an aldol condensation reaction between an unknown aldehyde and ketone, identified using IR spectroscopy. 2. The product will be analyzed using melting point, NMR, and IR to determine the structure. 3. A double crossed aldol condensation is expected to occur, forming a doubly conjugated ketone product, which often appears colored due to its conjugated system.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    33 views12 pages

    Week 8: Adol Condensation

    Uploaded by

    frenchisbomb
    1. The document describes an experiment to perform an aldol condensation reaction between an unknown aldehyde and ketone, identified using IR spectroscopy. 2. The product will be analyzed using melting point, NMR, and IR to determine the structure. 3. A double crossed aldol condensation is expected to occur, forming a doubly conjugated ketone product, which often appears colored due to its conjugated system.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 12

    Week 8: Adol Condensation

    Purpose
    Unknown aldehyde and unknown ketone will distinguished from one another with IR and then will be used to prepare an aldol condensation product.

    Identify of products will be found using H NMR and melting point of condensation product.

    Reaction

    Mechanism

    Procedure
    1. 2. 3. 4. 5. 6. Identify which vial contains the aldehyde (or ketone) using IR spectrum. After identification of vial, get .80mL and place it in 25mL Erlenmeyer flask. Add 4.0mL of 95% ethanol and 3.0 mL of 2.0M NaOH to the flask and stir (stir until no more precipitate) Heat the reaction using boiling water bath if precipitate formation is slow at room temp. Condensation products are colorfulwhat could cause the colors? Cool and place in ice bath and measure 8mL of 95% ethanol and 4mL of 4% acetic acid/ethanol solution is test tubes and place in ice bath.

    Procedure
    Vacuum filtrate to collect product and rinse with 4mL of EtOH followed by chilled acetic acid/ethanol solution and then the remaining with 4mL of chilled EtOH. Allow product to dry. Get MP and get TA to prepare NMR.

    If selected for NMR, prepare sample by dissolving 100mg of product in .3mL of CDCl3.

    Theory:IR Spectroscopy
    Aldehyde Fermi doublet: two distinct peaks around 2,700 cm-1 -2800 cm-1 and 2,800 cm-1 -2900 cm-1 Carbonyl stretch:conjugated with aromatic rings, which give lower wavenumbers to about 1700 cm-1 sp2 C-H stretch: >3000cm-1 Ketone No Fermi doublet

    Carbonyl stretch: no conjugation so around 1715 cm-1

    sp3 C-H stretch:<2900cm-1

    Theory:HNMR Spectroscopy
    Products
    Products should have aromatic rings from aldehyde as well as the R groups on from the ketone used Number of unique hydrogen, quantity of each time of hydrogen, electronic environment of each hydrogen, and the number of neighbors of each hydrogen this example you would see a singlet of integration 3, 2 doublets integration of 1 each, and the aromatic ring

    Theory: CNMR Spectroscopy


    Products
    Unlike HNMR there are no integration values in CNMR so CNMR tells you number of unique carbons, electronic environment of each carbon, and the number of neighbors of each carbon Look for functional groups and there arrangement to one another. Look for aromatic carbons, alkenes carbons, and the identifying R groups

    Theory: Double CrossedAldol Condensation Reaction


    General aldol: an enol/enolate reacts with a carbonyl compound to make a -hydroxyaldehyde or hydroxyketone which goes through condensation to , conjugated system Crossed: 2 carbonyl compounds, only 1 has -hydrogens
    Double: symmetrical ketone means either side is equal, with an -hydrogen that can be deprotonated for the reaction so a double condensation can occur as long as there are 2 equivalents of aldehyde to act as the electrophile
    Formation of a doubly conjugated ketone

    Reason for Condensation Step: OH is not a really good leaving group but the , conjugated product is favorable Colored products because it contains chromophoresshort chained conjugated system. The energy difference between molecular orbitals allows for the absorbance of visible light
    These short chains absorb higher energy levels t

    Sources of Error
    Loss of product due to inaccuracy in measuring.
    Ketone-ketone reaction and other side products Misidentification of aldehyde and ketone in IR
    Order of Addition Matters Fails to ensure 2 equivalents of aldehyde are added. Unable to have 2 condensations in all products

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