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11: Combined Problems 1

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    Combined Spectral Problems: IR, 13C & 1H*

    * All spectra are either from SDBS (Japan National Institute of Advanced Industrial Science and Technology) or simulated.

    • Propose structures for the following problems. Use the tables on the following pages to show your work.

    A. C6H12O2

    clipboard_e5eead3aba1f8ffe89b71a150af0dab7f.png

    clipboard_ee319be405ef57ae81e021401ef072f39.png

    clipboard_e07c1eb59b9a268326832b93afe30195f.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    B. C5H10O2

    clipboard_e880babb7c992477d1e4e820121501f89.png

    clipboard_eaa525ca262752b354d5052f9cfe90f42.png

    clipboard_eb010754c36708535a0bf68678a0043ea.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    C. C6H12O2

    clipboard_efea5c70af0ea08237885f90daef734a9.png

    clipboard_e17ffc4e3a4c8e52e2a7f815a0e761be7.png

    clipboard_e4d5e6d36f6c82b50b29f6bf01bdf3f4d.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:

     

     

     

     

     

     

    D. C5H8O4

    clipboard_e3f5f4a9c7949cfc17263724fbf121eaa.png

    clipboard_e0f8336685f343f10eafef71c85bccd73.png

    clipboard_e7a01b3d246616d15a8731ca60c8af795.png

    Note: OH peaks are not showing up in 1H-NMR because they have been exchanged with the solvent.

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    E. C4H6O2

    clipboard_e11ad7d5237876ac93ccecfdf2c88233b.png

    clipboard_e02066047d0c9653af4620475340354fb.png

    clipboard_e39bfa5c33a58b1e79dfd37e9c7bf1d10.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    F. C7H14O2

    clipboard_e5b7d13ab7870f7a1865b6499d18b364e.png

    clipboard_e58964edf4be53df27b6e58988520c11b.png

    clipboard_e6a768b3fe2d93fec201f7ccaf2c62554.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    G. C9H12

    clipboard_e8240cc8058562639e98c69e86f80e282.png

    clipboard_eb37450dc288e5510e769060232debefd.png

    clipboard_e13c0efadca7edea5dbd0711e1a2c6880.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    H. C10H12O

    clipboard_e9976a02461f00a63bb90e7768fae2ae5.png

    clipboard_e0d1bb181453ad8478b14f79cceb99776.png

    clipboard_e1358860500996b27900d44d2470ca1e2.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    I. C10H12O

    clipboard_e9d548784453e90d04668f6acc5adbb07.png

    clipboard_eb1abc361a89c2b3a458018de0a0ad832.png

    clipboard_e7d14b998a3d20b793a44698dfa5e70f5.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    J. C10H12O

    clipboard_e7a1faa4ba38d5bb84169f12e5cddadf2.png

    clipboard_e4c96db5c3b73cb958211d1f70cbef799.png

    clipboard_e85c77912eff2bd04dbf996309c8f899e.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    K. C10H12O

    clipboard_e1f1d8dc32a6b9a74c69ca9fd711d1804.png

    clipboard_e8fdb4f667e8aa4dca983ed7cba472664.png

    clipboard_eb46ae211edd84e43388c8447a91e003e.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    L. C10H12O

    clipboard_ea14b556444ecbb364e05c695be80c340.png

    clipboard_e37b7e326a8e0cf9b27a98a71266ddc01.png

    clipboard_e4dbbaea2224123ac38895c6d3c97cd4e.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

     

    M. C10H12O

    clipboard_e4208122918774c2ddedab8ff33633538.png

    clipboard_e8a8ac7790c2828e2fe4320783fc7a976.png

    clipboard_e234e57177e98ce06a68a59edfa587db5.png

    MF:         DU:

    IR
    Frequency Functional Group
       
       
       
       
       

     

    13C
    Chemical Shift Type of Bonding Environment
       
       
       
       
       
       
       

     

    1H
    Chemical Shift Integration Multiplicity Interpretation
           
           
           
           
           
           
           

     

    Proposed Structure:  

    This page titled 11: Combined Problems 1 is shared under a not declared license and was authored, remixed, and/or curated by Kate Graham.

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