Scribd Logo
Upload

Welcome to Scribd!

    • 276 views

    Exp 11 - Aldol Condensation

    Uploaded by

    Justin Bayne
    This document provides study questions for an experiment on aldol condensation reactions. It asks students to: 1) Analyze the aldol condensation of benzaldehyde and acetone to form dibenzalacetone, including identifying the limiting reagent and explaining the catalyst role. 2) Determine which hydrogen on a given molecule would be most acidic and likely to react first. 3) Match aldol donors and acceptors from a list to draw reaction products. 4) Suggest a synthesis to form a target molecule using aldol reactions. 5) Analyze an NMR spectrum to determine if a synthesized product is pure dibenzalacetone or contaminated. 6) Answer additional textbook

    Copyright:

    © All Rights Reserved
    Download as DOC, PDF, TXT or read online from Scribd

    Exp 11 - Aldol Condensation

    Uploaded by

    Justin Bayne
    276 views3 pages
    This document provides study questions for an experiment on aldol condensation reactions. It asks students to: 1) Analyze the aldol condensation of benzaldehyde and acetone to form dibenzalacetone, including identifying the limiting reagent and explaining the catalyst role. 2) Determine which hydrogen on a given molecule would be most acidic and likely to react first. 3) Match aldol donors and acceptors from a list to draw reaction products. 4) Suggest a synthesis to form a target molecule using aldol reactions. 5) Analyze an NMR spectrum to determine if a synthesized product is pure dibenzalacetone or contaminated. 6) Answer additional textbook

    Original Description:

    Aldol condensation questions for lab

    Copyright

    © © All Rights Reserved

    Available Formats

    DOC, PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    This document provides study questions for an experiment on aldol condensation reactions. It asks students to: 1) Analyze the aldol condensation of benzaldehyde and acetone to form dibenzalacetone, including identifying the limiting reagent and explaining the catalyst role. 2) Determine which hydrogen on a given molecule would be most acidic and likely to react first. 3) Match aldol donors and acceptors from a list to draw reaction products. 4) Suggest a synthesis to form a target molecule using aldol reactions. 5) Analyze an NMR spectrum to determine if a synthesized product is pure dibenzalacetone or contaminated. 6) Answer additional textbook

    Copyright:

    © All Rights Reserved
    Download as DOC, PDF, TXT or read online from Scribd
    Download as doc, pdf, or txt
    276 views3 pages

    Exp 11 - Aldol Condensation

    Uploaded by

    Justin Bayne
    This document provides study questions for an experiment on aldol condensation reactions. It asks students to: 1) Analyze the aldol condensation of benzaldehyde and acetone to form dibenzalacetone, including identifying the limiting reagent and explaining the catalyst role. 2) Determine which hydrogen on a given molecule would be most acidic and likely to react first. 3) Match aldol donors and acceptors from a list to draw reaction products. 4) Suggest a synthesis to form a target molecule using aldol reactions. 5) Analyze an NMR spectrum to determine if a synthesized product is pure dibenzalacetone or contaminated. 6) Answer additional textbook

    Copyright:

    © All Rights Reserved
    Download as DOC, PDF, TXT or read online from Scribd
    Download as doc, pdf, or txt
    of 3

    Chem 202L by Dr.

    Gonzales Study Questions

    Exp # 11 (Quiz 9): Aldol Condensation

    The answer of these questions will be part of your notebook grade. (Must show all work for FULL credit).
    1. In today experiment you will perform the aldol condensation between benzaldehyde (PhCHO) and acetone
    to synthesize dibenzalacetone. Answer the following questions regarding this reaction:
    a. This reaction is an example of a mixed aldol condensation. Why is only one product formed and no
    mixture of compounds are obtained like in other aldol condensations? (Hint: Benzaldehyde cannot
    undergo “ALDOL” reaction by itself in presence of strong base (NaOH). Why?)

    b. Look at the mmols of the reagents used in this reaction and specify the limiting reagent.

    c. Explain why the NaOH is a catalyst in this reaction, rather than a reagent. (Hint - look at the reaction
    mechanism.)

    d. Usually an aldol condensation must be heated in order to dehydrate the beta-hydroxy ketone to form the
    C=C. What is different about this product that causes it to dehydrate at room temperature?

    e. Why does this product have a yellow color?

    f. The IR spectrum of dibenzalacetone shows the C=O peak at lower wavenumbers (1639 cm -1) than
    standard C=O frequency (1715 cm-1)? Why do you think?

    g. How would you change the procedures in this experiment if you wished to synthesize benzalacetone,
    C6H5CH=CHCOCH3? Benzalacetophenone, C6H5CH=CHCOC6H5?

    h. The name dibenzalacetone does not completely characterize the molecules made in this experiment.
    There are 3 isomeric dibenzalacetones, one melting at 100-110 °C, max = 330 nm, 34,300; another
    melting at 60 °C, max = 295 nm, 20,000; and a third, a liquid with max = 287 nm 11,000.
    Draw the structures of the three geometric isomers of dibenzalacetone (Z,Z; Z,E; E,E), and assign each
    one to the three molecules described in the previous paragraph.

    i. Write the detailed mechanism for the formation of dibenzalacetone from benzalacetone and
    benzaldehyde.

    2. In the following compound, which hydrogen (designated in bold) is the most acidic hydrogen, and hence the
    most likely to react with base in the first step of a base-catalyzed aldol condensation reaction?
    O O O O
    CH3CH2CH2 CH3CH2CH2 CH3CH2CH2 CH3CH2CH2
    H H H H
    a) b) c) d)

    Dr. L. Gonzales Page 1


    Chem 202L by Dr. Gonzales Study Questions
    3. Aldol Condensation proceeds by carbon-carbon bond formation between an enolate donor and a carbonyl acceptor.
    For each of the following aldol products (1 through 5) select a donor and an acceptor compound from the list of
    compounds A through H. Enter the letter corresponding to your selection in the appropriate answer box.
    Donor Acceptor

    __ ___

    __ ___

    __ ___

    _ ___

    __ ___

    Check answers at: http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/Questions/Match/aldol.htm

    4. Using aldol or crossed aldol condensation reactions, suggest a synthesis of the following compound:
    CH2CH3

    CH3CH2CH2CH C CHO
    5. A student synthesized 4’-methoxychalcone (see structure in the graph A) below) according to the procedure
    you will use in this lab. The 1H-NMR of the product he isolated is given below.
    a. Determine which one is the enolate donor compound and the carbonyl acceptor compound to form 4’-
    methoxychalcone and assign structure of the enolate and carbonyl compound on the spectrum B) and C).
    b. Analyze H-NMR spectrum A) of product and determine if the product is pure or it is contaminated. If it
    is contaminated, what is it contaminated with?

    Dr. L. Gonzales Page 2


    Chem 202L by Dr. Gonzales Study Questions

    A)

    B) C)

    6. Questions: 6-134, 6-135, 6-136b, pag. 316, lab textbook 6e OR 6-132, 6-133, 6-134b, pag. 316, lab textbook
    5e.

    Dr. L. Gonzales Page 3

    You might also like