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    CHEM 2444-03 Organic Chemistry II Worksheet #7: Carbonyl Additions M W Peczuh

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    sun7biswas
    The document provides structures and reaction steps for organic chemistry problems involving carbonyl compounds. It lists multiple starting materials and reagents that can be used to synthesize various carbonyl derivatives through addition, oxidation, and reduction reactions.

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    © All Rights Reserved
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    CHEM 2444-03 Organic Chemistry II Worksheet #7: Carbonyl Additions M W Peczuh

    Uploaded by

    sun7biswas
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    The document provides structures and reaction steps for organic chemistry problems involving carbonyl compounds. It lists multiple starting materials and reagents that can be used to synthesize various carbonyl derivatives through addition, oxidation, and reduction reactions.

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    The document provides structures and reaction steps for organic chemistry problems involving carbonyl compounds. It lists multiple starting materials and reagents that can be used to synthesize various carbonyl derivatives through addition, oxidation, and reduction reactions.

    Copyright:

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

    CHEM 2444-03 Organic Chemistry II Worksheet #7: Carbonyl Additions M W Peczuh

    Uploaded by

    sun7biswas
    The document provides structures and reaction steps for organic chemistry problems involving carbonyl compounds. It lists multiple starting materials and reagents that can be used to synthesize various carbonyl derivatives through addition, oxidation, and reduction reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
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    CHEM 2444-03 Organic Chemistry II Worksheet #7: Carbonyl Additions

    M W Peczuh

    1. Provide structures for A – K. (22 points, 2 points each)

    O
    i)Ph-MgBr H2SO4
    ii) H3O+
    A B
    heat

    O
    Ph3P CH3 Br
    H
    nBu-Li
    C

    O
    mCPBA
    D

    i)Ph-MgBr H2SO4(cat)
    O C O
    ii) H3O+
    E F
    CH3OH

    O NH2

    i)NaBH4 PBr3 NaCN i)LiAlH4


    ii) H3 O+
    G H CH3CH2OH
    I ii) H3O+

    O
    H+ (cat) i)allyl-MgCl
    J K
    H CH3NH2 ii) H3O+
    2. Show how to convert cyclopentanone to the compounds shown. You may use any other
    reagents/conditions necessary to complete the syntheses. (5 syntheses, 3 points each = 15 points total)

    O
    H3CO OH
    O O
    OH Cl

    O
    H3CO OH
    O O
    Cl

    H3CO OH
    Cl O

    H3CO OH
    Cl O

    OH
    O
    3. Provide structures for L – P.(15 points, 3 points each)

    1) MgBr ; H O+
    3

    O 2) PCC L
    3) MgBr ; H O+
    3

    1) NaNH2
    2) acetaldehyde; H3O+

    3) PCC
    M
    4) CH3MgBr; H3O+

    1) H2SO4(cat), H2O
    2) H2CrO4
    N
    3) CH3CH2NH2
    4) NaBH4
    5) benzoyl chloride

    1)KOtBu
    Br 2) OsO4, NMO
    O
    3) H2SO4(cat), acetone

    1) Br2, FeBr3
    2) Mg(0)
    3) CO2; H3O+
    P
    4) SOCl2 NH2
    5) 2 eq.

    6) LAH; H2O

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