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    Tutorial 7

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    Nicholas Ow
    1) The document provides information on organic synthesis and mechanisms including spectroscopy, alcohols, ethers, and epoxides. It includes 5 questions related to assigning proton signals, proposing structures based on data, identifying compounds from NMR and IR spectra, proposing synthetic routes, and explaining reaction mechanisms. 2) Question 4 asks to propose synthetic routes for several compounds using available reagents which include bromine, alcohol, bromoalkane, and inorganic reagents. 3) Question 5 briefly explains the formation of an epoxide under basic conditions from an alkyl chloride and the lack of epoxide formation under the same conditions when the starting material is an alkyl bromide.

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    Tutorial 7

    Uploaded by

    Nicholas Ow
    225 views2 pages
    1) The document provides information on organic synthesis and mechanisms including spectroscopy, alcohols, ethers, and epoxides. It includes 5 questions related to assigning proton signals, proposing structures based on data, identifying compounds from NMR and IR spectra, proposing synthetic routes, and explaining reaction mechanisms. 2) Question 4 asks to propose synthetic routes for several compounds using available reagents which include bromine, alcohol, bromoalkane, and inorganic reagents. 3) Question 5 briefly explains the formation of an epoxide under basic conditions from an alkyl chloride and the lack of epoxide formation under the same conditions when the starting material is an alkyl bromide.

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    1) The document provides information on organic synthesis and mechanisms including spectroscopy, alcohols, ethers, and epoxides. It includes 5 questions related to assigning proton signals, proposing structures based on data, identifying compounds from NMR and IR spectra, proposing synthetic routes, and explaining reaction mechanisms. 2) Question 4 asks to propose synthetic routes for several compounds using available reagents which include bromine, alcohol, bromoalkane, and inorganic reagents. 3) Question 5 briefly explains the formation of an epoxide under basic conditions from an alkyl chloride and the lack of epoxide formation under the same conditions when the starting material is an alkyl bromide.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    Download as pdf or txt
    225 views2 pages

    Tutorial 7

    Uploaded by

    Nicholas Ow
    1) The document provides information on organic synthesis and mechanisms including spectroscopy, alcohols, ethers, and epoxides. It includes 5 questions related to assigning proton signals, proposing structures based on data, identifying compounds from NMR and IR spectra, proposing synthetic routes, and explaining reaction mechanisms. 2) Question 4 asks to propose synthetic routes for several compounds using available reagents which include bromine, alcohol, bromoalkane, and inorganic reagents. 3) Question 5 briefly explains the formation of an epoxide under basic conditions from an alkyl chloride and the lack of epoxide formation under the same conditions when the starting material is an alkyl bromide.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
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    School of Physical & Mathematical Sciences

    Division of Chemistry & Biological Chemistry

    H3 Organic Synthesis and Mechanism - Tutorial 7


    Spectroscopy, Alcohols, Ethers and Epoxides

    1) With the coupling information given, assign the signals due to Ha, Hb and
    Hc .
    Hb Ha Jab = 11.8 Hz
    Jbc = 0.9 Hz
    Hc CN Jac = 18 Hz

    2) Propose a structure consistent with each set of data.


    a) C9H10O2 , IR absorption at 1718 cm-1

    b) C9H12 , IR absorption at 2850-3150 cm-1


    School of Physical & Mathematical Sciences
    Division of Chemistry & Biological Chemistry

    3) A compound with molecular formula C6H10 has a 13C NMR spectrum with 4
    lines (δ = 27, 30, 67, 93 ppm). The IR spectrum is shown below. Identify
    the compound.

    4) The following organic compounds are available in your laboratory:


    O
    Br OH Br

    Using the above compounds (not all of them may be useful), and any other
    organic or inorganic reagents, propose a synthetic route each for the
    following compounds:
    OH
    HO HO OH
    OH
    OH OH

    OH

    OH

    5) Briefly explain the following.

    (a) OH
    base
    O

    Cl
    OH
    base
    no epoxide formation
    Cl

    O
    (b)
    OH /H+
    OH
    O

    OH

    O O

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