Scribd Logo
Upload

Welcome to Scribd!

  • 140 views

    Tutorial 2

    Uploaded by

    Marlinda Marcus Lundang
    This document contains 6 questions regarding organic chemistry reactions and syntheses. Question 1 asks about the asymmetric synthesis of amino acids from proline. Question 2 asks about separating enantiomers of the drug tazadolene. Question 3 asks how to make enantiomerically enriched samples of compounds. Question 4 asks about synthesizing the optically active compound "Disparlure". Question 5 asks for structures of intermediates in an asymmetric reaction. Question 6 asks for missing structures in a natural product synthesis and mechanisms.

    Copyright:

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

    Tutorial 2

    Uploaded by

    Marlinda Marcus Lundang
    140 views3 pages
    This document contains 6 questions regarding organic chemistry reactions and syntheses. Question 1 asks about the asymmetric synthesis of amino acids from proline. Question 2 asks about separating enantiomers of the drug tazadolene. Question 3 asks how to make enantiomerically enriched samples of compounds. Question 4 asks about synthesizing the optically active compound "Disparlure". Question 5 asks for structures of intermediates in an asymmetric reaction. Question 6 asks for missing structures in a natural product synthesis and mechanisms.

    Original Description:

    Tutorial organic

    Copyright

    © © All Rights Reserved

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    This document contains 6 questions regarding organic chemistry reactions and syntheses. Question 1 asks about the asymmetric synthesis of amino acids from proline. Question 2 asks about separating enantiomers of the drug tazadolene. Question 3 asks how to make enantiomerically enriched samples of compounds. Question 4 asks about synthesizing the optically active compound "Disparlure". Question 5 asks for structures of intermediates in an asymmetric reaction. Question 6 asks for missing structures in a natural product synthesis and mechanisms.

    Copyright:

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

    Tutorial 2

    Uploaded by

    Marlinda Marcus Lundang
    This document contains 6 questions regarding organic chemistry reactions and syntheses. Question 1 asks about the asymmetric synthesis of amino acids from proline. Question 2 asks about separating enantiomers of the drug tazadolene. Question 3 asks how to make enantiomerically enriched samples of compounds. Question 4 asks about synthesizing the optically active compound "Disparlure". Question 5 asks for structures of intermediates in an asymmetric reaction. Question 6 asks for missing structures in a natural product synthesis and mechanisms.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 3

    SCES3120/SIC3002: ORGANIC CHEMISTRY III

    SID3002: ADVANCE ORGANIC CHEMISTRY


    SEMESTER 2, 2017/2018
    TUTORIAL 2

    1. Explain how this asymmetric synthesis of amino acids, starting with natural proline, works.
    Explain the stereoselectivity of each reaction.

    H H H2, Pd
    NH3 O CF3CO2H
    CO2H O
    N N CO2Me N N
    H NH NH
    O O
    (S)-proline O O
    HO R
    (A) R (B) (C) R

    H
    O H3O+ HO2C NH
    N CO2H +
    NH N H R
    O H
    H R
    (E)
    (D)

    2. This is a synthesis of the racemic drug tazadolene. If the enantiomers of the drug are to be
    evaluated for biological activity, they must be separated. At which stage would you advocate
    separating the enantiomers and how would you do it?

    3. How would you make enantiomerically enriched samples of these compounds (either
    enantiomer)?
    4. Show how would you synthesis optically active compound called “Disparlure” from the given
    starting material?

    5. Give the structure of products J-N in the asymmetric reaction shown below. Give the correct
    stereochemistry where ever possible.

    Ph O Ph O
    H2 H2
    Et OH Et OH
    (J) (R)-BINAP H
    (S)-BINAP CH3
    Ru(OAc)2 H CH3
    Ru(OAc)2

    Ph
    H2 H2
    (K) Et OH (L)
    (S)-BINAP CH3 (R)-BINAP
    Ru(OAc)2 Ru(OAc)2

    6. Reaction scheme shown below are the synthesis pathway of “Apoptotic Natural Myrcene-
    Derived Cyclohexenyl Chalcone.
    i. Give the structure of the missing intermediate 1, 3, 5, 7, and 9.
    ii. Show the mechanism for the conversion of 2 to 3 and 7 to 8.
    LiOH, H2O2
    THF, H2O MeONHOMe MeMgBr
    (3) O
    (5) Bu2O, 0 oC O
    OH CH3
    (4) (+)-fislatifolione
    (6)

    Prepared by Prof Azhar


    26-02-2018

    You might also like