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    HW 10

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    This document provides structures of various carbohydrates and asks students to: 1) Draw structures of specific carbohydrates including D-galactose, D-xylose, and a D-glucose derivative. 2) Indicate whether carbohydrates are reducing or non-reducing. 3) Predict products of reactions involving carbohydrates and reagents like silver nitrate and sulfuric acid. 4) Propose a mechanism for the Strecker synthesis of aminonitriles from aldehydes, ammonia, and hydrogen cyanide. 5) Propose methods to achieve specific transformations involving functional groups like methyl ethers and nitriles.

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    HW 10

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    17 views2 pages
    This document provides structures of various carbohydrates and asks students to: 1) Draw structures of specific carbohydrates including D-galactose, D-xylose, and a D-glucose derivative. 2) Indicate whether carbohydrates are reducing or non-reducing. 3) Predict products of reactions involving carbohydrates and reagents like silver nitrate and sulfuric acid. 4) Propose a mechanism for the Strecker synthesis of aminonitriles from aldehydes, ammonia, and hydrogen cyanide. 5) Propose methods to achieve specific transformations involving functional groups like methyl ethers and nitriles.

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    This document provides structures of various carbohydrates and asks students to: 1) Draw structures of specific carbohydrates including D-galactose, D-xylose, and a D-glucose derivative. 2) Indicate whether carbohydrates are reducing or non-reducing. 3) Predict products of reactions involving carbohydrates and reagents like silver nitrate and sulfuric acid. 4) Propose a mechanism for the Strecker synthesis of aminonitriles from aldehydes, ammonia, and hydrogen cyanide. 5) Propose methods to achieve specific transformations involving functional groups like methyl ethers and nitriles.

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    © All Rights Reserved
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    17 views2 pages

    HW 10

    Uploaded by

    p
    This document provides structures of various carbohydrates and asks students to: 1) Draw structures of specific carbohydrates including D-galactose, D-xylose, and a D-glucose derivative. 2) Indicate whether carbohydrates are reducing or non-reducing. 3) Predict products of reactions involving carbohydrates and reagents like silver nitrate and sulfuric acid. 4) Propose a mechanism for the Strecker synthesis of aminonitriles from aldehydes, ammonia, and hydrogen cyanide. 5) Propose methods to achieve specific transformations involving functional groups like methyl ethers and nitriles.

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    of 2

    CHEM 203 HOMEWORK 10 Carbohydrates

    1. Write the structure of:


    a. A Fischer projection of D-galactose:

    HO OH
    H
    O
    H
    HO
    HO H OH
    H
    D-galactose

    b. The more thermodynamically stable pyranose form of D -xylose:

    CHO
    H OH
    HO H
    H OH
    OH
    D-xylose

    c. The α-methyl glycoside derivative of D-glucose:

    CHO
    H OH
    HO H
    H OH
    H OH
    OH
    D-glucose

    d. A Fischer projection of any D -aldopentose and one of any L-aldopentose

    e. A Fischer projection of a D-ketohexose


    CHEM 203 HOMEWORK 10 p. 2

    2. Indicate whether the following carbohydrates are reducing or nonreducing

    OH
    HO O
    HO OH HO OH
    O H O OH
    O O HO HO
    HO H HO OH O O
    HO HO O
    O HO HO
    HO H OH
    HO OH HO OH
    H OH
    HO

    3. Predict the product(s) of the following reactions:

    H OH OH
    OH Ag(NH3)2NO3 OH
    O O
    HO
    a. HO HO
    aq. NH3
    H H OH HO
    H O
    d. O dil. aq.
    H HO
    H OH
    CH3CH2OH HO H2SO4
    O
    HO HO
    b. HO HO
    cat. H2SO4 OH O
    HO H OH – H2O O
    H
    OH
    HO OH HO
    H
    O aq. NH3 excess NaH
    H e. product of
    c. HO question b.
    HO H OH excess CH3I
    H

    4. The world demand for aminoacids is so large that many such compounds have to be produced by synthesis,
    rather than by extraction from naturally occurring proteinaceous material. A key reaction in the industrial
    preparation of aminoacids is the so-called Strecker synthesis (diagram below). Thus, an aldehyde, e.g.,
    phenylacetaldehye, A, ammonia, ammonium chloride (pKa ≈ 9), and hydrogen cyanide (pKa ≈ 10) are
    combined to give an aminonitrile, B, which is then transformed into an aminoacid, e.g., phenylalanine, C,
    by a reaction that you will study in CHEM 213. Propose a mechanism for the formation of B.

    NH3, NH4Cl CN COOH


    CHO
    HCN NH2 NH2
    A B C

    note: meterorites contain several simple aminoacids, which are believed to form by a Strecker reaction
    in outer space, where simple aldehydes, ammonia, and HCN are common.

    5. Propose a method to achieve the following transformations:

    CN
    a. b.
    CH3O O OCH3 OH

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