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    Chapter 23. Carbonyl Condensation Reactions

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    張湧浩
    This document summarizes carbonyl condensation reactions including aldol reactions, Claisen condensations, Michael additions, and Robinson annulations. Specific reactions are given to predict products and identify starting materials. Intramolecular reactions like aldol condensations and Robinson annulations are also discussed. Key reaction types covered include addition, condensation, and dehydration reactions of carbonyl compounds.

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    Chapter 23. Carbonyl Condensation Reactions

    Uploaded by

    張湧浩
    41 views19 pages
    This document summarizes carbonyl condensation reactions including aldol reactions, Claisen condensations, Michael additions, and Robinson annulations. Specific reactions are given to predict products and identify starting materials. Intramolecular reactions like aldol condensations and Robinson annulations are also discussed. Key reaction types covered include addition, condensation, and dehydration reactions of carbonyl compounds.

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    problem_chp23-4

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    This document summarizes carbonyl condensation reactions including aldol reactions, Claisen condensations, Michael additions, and Robinson annulations. Specific reactions are given to predict products and identify starting materials. Intramolecular reactions like aldol condensations and Robinson annulations are also discussed. Key reaction types covered include addition, condensation, and dehydration reactions of carbonyl compounds.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    41 views19 pages

    Chapter 23. Carbonyl Condensation Reactions

    Uploaded by

    張湧浩
    This document summarizes carbonyl condensation reactions including aldol reactions, Claisen condensations, Michael additions, and Robinson annulations. Specific reactions are given to predict products and identify starting materials. Intramolecular reactions like aldol condensations and Robinson annulations are also discussed. Key reaction types covered include addition, condensation, and dehydration reactions of carbonyl compounds.

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    Chapter 23.

    Carbonyl
    Condensation Reactions
    23.1
    Predict the aldol reaction product of the following
    ketone.
    O NaOH
    2 aldol product
    Ethanol

    1. 2.
    O OH
    O OH

    3. 4.
    O
    O OH

    HO

    5.
    O
    OH
    23.1 answer
    O NaOH
    2 aldol product
    Ethanol

    1. 2.
    O OH
    O OH

    3. 4.
    O
    O OH

    HO

    5.
    O
    OH
    23.2 O
    OH
    2 C Enone product
    CH3CH2 H heat
    (a) (b)
    H

    O O

    (c) (d)
    H
    H

    O
    O
    23.2 answer
    (a) (b)
    H

    O O

    (c) (d)
    H
    H

    O
    O
    23.3 Which starting material(s) will produce the
    following aldol reaction product?

    2.
    1.

    3.
    4.
    2

    5.

    2
    23.3 answer
     

    2.
    1.

    2

    3.
    4.
    2

    5.

    2
    23.4 Which pair of compounds would be required to
    prepare the following aldol product?

    2.
    1. O O
    O
    O H +
    H + O

    4.
    3. O
    O O
    H +
    + O
    H

    5.
    O

    H +
    O
    23.4 answer 

    2.
    1. O O
    O
    O H +
    H + O

    3. 4.
    O
    O O
    +
    H +  H O

    5.
    O

    H +
    O
    23.5 Which of the following reactions will yield the
    compound shown below?

    1. 2.

    3.
    4.

    5.
    23.5 answer 

    1. 2.

    3.
    4.

    intramolecular aldol condensation

    5.
    O
    23.6
    NaOCH3
    2 C
    CH3CH2 OCH3

    (a) OCH3
    (b)
    OCH3
    OCH3

    O O
    O

    (c) (d) O

    O
    OCH2CH3
    OCH3

    O O

    O
    23.6 answer
    (a) OCH3
    (b)
    OCH3
    OCH3

    O O
    -keto ester
    O

    (c) (d) O

    O
    OCH2CH3
    OCH3

    O O
    O

    A -keto ester is produced from a Claisen


    condensation.
    O

    23.7 OH
    +

    O O
    O

    (a) (b)

    O O
    O

    (c) O O
    (d) O

    O
    O
    23.7 answer
    O

    (a) (b)

    O O
    O
    (c) O O
    (d) O

    O
    O

    The Michael Reaction:


    the -diketone undergoes an 1,4-addition.
    23.8 Predict the outcome of the following reaction.

    2.
    1.

    3. 4.

    5.
    23.8 answer

    2.
    1.

    3. 4.

    5. The Michael Reaction:


    Enamines undergoes an
    1,4-addition
    O
    23.9
    OH
    + Robinson
    heat annulation
    O O
    O

    (a) (b)

    O O
    O
    (c) O O
    (d)

    O O
    23.9 answer
    O

    (a) (b)

    O O
    O
    (c) O O
    (d)

    O O
    In the Robinson annulation, (1) Michael reaction (1,4-
    addition) (2) the -diketone undergoes an
    intramolecular aldol condensation, followed by
    dehydration.

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