MDC Calculating Percent Yield Before & After Recrystallization Report

Instructions:

  • Include an introduction explaining the reaction for      this experiment.
  • Write down the balanced chemical reaction for the      experiment.
  • Draw the mechanism for the reaction carried out in the      experiment.
  • Summarize the video below. Write them as      procedures or instructions for someone to carry out in a lab      setting.
  • For      example:
  • 1-      Protect the hands and arms by wearing gloves
  • 2- Weigh 0.3g of X compound and 0.5g      of Z compound. Transfer the reagents
  • 3-       Add ……. Etc
  • 4-…..etc
  • THE VIDEO THAT YOU MUST SUMMARIZE IS THIS ONE :

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  • Calculate limiting reagent, percent yield and percent      recovery after recrystallization based on the data below:
  • Compounds Amounts

    anthracene 0.520 g

    maleic anhydride 0.320 g

    crude Diels Alder product 0.623 g

    recrystallized Diels Alder product 0.550 g

    Experimental melting point of recrystallized product 266 – 268 Celsius

    Xylenes (solvent) 35 mL

  • Discuss      errors such as low or high yields, melting points, etc.
  • Cite references used to help you write this lab report.
  • Answer      post lab questions 1-4 from handout on page 163
  • Post-Laboratory Questions

    1. Calculate the percent yield for your product, before and after recrystallization.

    2. Calculate the percent recovery from the recrystallization.

    3. The product of this reaction can be hydrolyzed by water. Show the product of hydrolysis.

    4. Recrystallizing an anhydride (such as the product of this reaction) from water or from an alcohol is rarely a good idea. Explain why.

    5. (a) Compare the carbonyl region of your IR spectrum with that of maleic anhydride. What are the similarities? What are the differences? (b) Does your IR spectrum allow you to confirm that the structure of the product is a combination of the two reactants? Briefly explain.

    USE APA EDITION 7 FORMAT

    YOU MUST WRITE ON YOUR OWN, USE THE HANDOUT PAPER AND THE VIDEOS AS A REFERENCE TOO. DO NOT ADD CITATIONS OR QUOTATIONS PLEASETHIS VIDEOS BELOW ARE ADDITIONAL INFORMATION:

    https://youtu.be/z9KGlRNgnbE

    https://youtu.be/sfWmd5fAo5w

    https://youtu.be/HdvrTQpzfjc

    https://youtu.be/_sO6at1VcCs 12
    modular
    publisher:
    . laboratory.
    program
    SYNT
    in
    chemistry
    717
    organic editor: Joe Jeffers
    H.A. Neidig
    The Diels-Alder Reaction
    of Anthracene with
    Maleic Anhydride
    prepared by L. G. Wade, Jr., Whitman College
    PURPOSE OF THE
    EXPERIMENT
    Use the Diels-Alder reaction to form a bridged polycyclic anhydride.
    Recrystallize the product and characterize it by using melting point and
    infrared spectroscopy.
    BACKGROUND REQUIRED
    You should be familiar with reflux techniques, vacuum filtration, recrystallization, melting point measurement, and infrared spectroscopy.
    EXPERIMENTAL OPTIONS
    Semi-Microscale Diels-Alder Reaction
    Microscale Diels-Alder Reaction
    BACKGROUND
    INFORMATION
    Otto Diels, Professor of Chemistry at the University of Kiel, Germany,
    and his student Kurt Alder published a paper in 1928 on additions of
    electron-poor alkenes and alkynes to electron-rich dienes to form cyclohexenes and cyclohexadienes. These [4 + 2] cycloadditions came to be
    known as Diels-Alder reactions. Diels and Alder received the 1950 Nobel Prize in chemistry for this work.
    The Diels-Alder reaction is one of the most useful synthetic reactions in organic chemistry. In one step the reaction forms a sixmembered ring with one or two double bonds from an open-chain compound, as shown in Equations 1 and 2 on the next page. A diene is the
    4-1t-electroncomponent. It is electron-rich, like a nucleophile in a Lewis
    acid-base reaction. Simple dienes like 1,3-butadiene are sufficiently
    electron-rich to react, but electron-releasing groups such as alkyl groups
    (-R) or alkoxy groups (-OR) enhance a diene’s reactivity.
    The 2-1t-electron component is called a dienophile (“lover of dienes”). Good dienophiles contain relatively electron-poor double bonds
    or triple bonds; at least one strongly electron-withdrawing group (W) is
    needed. Therefore, ethylene and acetylene are not good dienophiles.
    Because the reaction is concerted-that is, bond breaking and bond
    forming take place in the same step-the
    stereochemistry of the
    Copyright @ 1998 by Chemical Education Resources,
    Inc., P.O. Box 357, 220 S. Railroad, Palmyra, Pennsylvania
    17078
    No part of this laboratory program may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher. Printed in the United
    States of America
    156
    SYNT 717: The Diels-Alder ReaCtion of Anthracene with Maleic Anhydride
    (
    +
    diene
    (W
    (Eq.l)
    adduct
    dienophile
    (alkene)
    W
    I
    (
    +
    diene
    C
    (Eq. 2)
    III
    C
    I
    H
    dienophile
    (alkyne)
    adduct
    reactants and the symmetry of their molecular orbitals control the
    stereochemistry of the products. Using well-chosen reactants, a chemist
    can control the stereochemistry of a Diels-Alder product at up to four
    carbon atoms, as shown in Figure 1.
    o
    II
    ( (
    ~
    +
    ~ COOCH3
    -+-
    I
    a
    H
    C-OCH3
    I
    :
    C-OCH3
    II
    o
    = COOCH3
    H
    (cis, but not trans)
    (trans, but not cis)
    but not
    (endo)
    OCH3
    (
    CH30.
    +
    (exo)
    H
    (=N_ a~N
    (cis
    -1,2)
    and not
    (trans -1,2)
    (1,3)
    Figure 1 Stereochemical patterns of Diels-Alder reactions
    In this experiment, maleic anhydride is used as the dienophile.
    Maleic anhydride is an excellent dienophile because two strongly
    electron-withdrawing groups are attached to the double bond.
    The diene is anthracene, which is commonly thought of as an aromatic compound, and not as a diene. However, in polynuclear aromatic
    compounds like anthracene, each individual ring may not be as well stabilized as an isolated benzene ring. Anthracene has only 141t electrons,
    compared with 18 needed for three fully independent aromatic rings.
    @ 1998 Chemical Education Resources
    156
    SYNT 717: The Diels-Alder ReaCtion of Anthracene with Maleic Anhydride
    (
    +
    diene
    (W
    (Eq.1)
    adduct
    dienophile
    (alkene)
    W
    I
    (
    C
    +
    diene
    (Eq. 2)
    III
    C
    I
    H
    dienophile
    (alkyne)
    adduct
    reactants and the symmetry of their molecular orbitals control the
    stereochemistry of the products. Using well-chosen reactants, a chemist
    can control the stereochemistry of a Diels-Alder product at up to four
    carbon atoms, as shown in Figure 1.
    o
    II
    ( (
    ~
    +
    ~ COOCH3
    -+-
    I
    a
    H
    C-OCH3
    I
    :
    C-OCH3
    II
    o
    = COOCH3
    H
    (cis, but not trans)
    (trans, but not cis)
    but not
    (endo)
    OCH3
    (
    CH30.
    (exo)
    H
    CH3~H
    +
    (=N_ 6

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