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    Assignment - 1 - Furans

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    Jitendra Kumawat 17115
    This document presents several organic chemistry problems involving the synthesis and reactions of furan: 1) It asks to predict the products and mechanisms for several transformations of furan derivatives involving reactions such as addition, oxidation, and cross-coupling. 2) It also asks to predict the products of metathesis and hydrolysis reactions of furan derivatives using various catalysts. 3) Finally, it asks to provide step-by-step mechanisms to synthesize several multifunctional furan derivatives and to predict pathways for functionalizing furans using reactions like cross-coupling, acid-catalyzed rearrangement, and oxidation.

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    Assignment - 1 - Furans

    Uploaded by

    Jitendra Kumawat 17115
    59 views2 pages
    This document presents several organic chemistry problems involving the synthesis and reactions of furan: 1) It asks to predict the products and mechanisms for several transformations of furan derivatives involving reactions such as addition, oxidation, and cross-coupling. 2) It also asks to predict the products of metathesis and hydrolysis reactions of furan derivatives using various catalysts. 3) Finally, it asks to provide step-by-step mechanisms to synthesize several multifunctional furan derivatives and to predict pathways for functionalizing furans using reactions like cross-coupling, acid-catalyzed rearrangement, and oxidation.

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    FURANS ASSI

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    This document presents several organic chemistry problems involving the synthesis and reactions of furan: 1) It asks to predict the products and mechanisms for several transformations of furan derivatives involving reactions such as addition, oxidation, and cross-coupling. 2) It also asks to predict the products of metathesis and hydrolysis reactions of furan derivatives using various catalysts. 3) Finally, it asks to provide step-by-step mechanisms to synthesize several multifunctional furan derivatives and to predict pathways for functionalizing furans using reactions like cross-coupling, acid-catalyzed rearrangement, and oxidation.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    59 views2 pages

    Assignment - 1 - Furans

    Uploaded by

    Jitendra Kumawat 17115
    This document presents several organic chemistry problems involving the synthesis and reactions of furan: 1) It asks to predict the products and mechanisms for several transformations of furan derivatives involving reactions such as addition, oxidation, and cross-coupling. 2) It also asks to predict the products of metathesis and hydrolysis reactions of furan derivatives using various catalysts. 3) Finally, it asks to provide step-by-step mechanisms to synthesize several multifunctional furan derivatives and to predict pathways for functionalizing furans using reactions like cross-coupling, acid-catalyzed rearrangement, and oxidation.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    of 2

    INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL

    Department of Chemistry
    Assignment – 1 (CHM 318)

    Synthesis and Reactions of Furan

    Q1: Predict the product and write suitable mechanism for the following transformations

    a) Ph
    O b) Me OH
    4 equiv MeOH 1 mol% (PhCN)2PdCl2
    1 mol% [(Ph3P)Au]OTf ?
    ? THF, rt, 10 h
    CH2Cl2, rt, 15 min OH Ph

    Q2: Predict the product for the following transformation

    Me Ph MesN NMes
    10 mol% Grubbs
    O iPr ? Cl Ru
    toluene, 60 °C Cl
    OEt Ph
    then cat. TFA, rt PCy3
    Grubbs catalyst

    Q3: Predict the product for the following transformations

    a) cat. Pd(dppf)Cl2 b) O
    SiMe3 CsF
    Br
    +
    MgBr − ? ?
    O S Et2O, 30 °C to rt D
    OTf MeCN, rt
    5h

    I SnBu3
    c) cat. Pd(PPh3)4 d)
    + ? MeO2C Br
    ?
    O ZnCl O cat. Pd(PPh3)4
    THF, rt, 2 h
    CO2H DMA, D

    CO2H
    −
    e) 1) s-BuLi, 78 °C I CO2H
    N Me THF, 30 min
    Me3Si O Me ?
    O − 2, THF
    2) ZnBr cat. Pd(PPh3)4 N Me
    20 °C THF, reflux, 16 h Me3Si Me
    O
    O

    Q4: How to synthesize following furans? Write the all steps and suitable mechanisms.
    OMe
    O Me
    a) b) Me c)
    O

    Me O
    O
    Q5: Predict the suitable pathway for the following transformations
    a) NHAc
    B(OH)2 O
    Br cat. Pd(PPh3)4
    +
    O CHO DMF, NEt3,100 °C, 2 h
    N

    b) O
    H
    CONH2 N
    Ph 5 mol% pTSA O
    + Ph
    O NH
    OH NH2 MeCN, 90 °C, 24 h

    c)
    2 mol% AuCl3 O
    O
    O
    MeCN, rt
    OH

    ***************************************************************************

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