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    Problem Set #8: Massachusetts Institute of Technology 5.13, Fall 2006

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    Karthikeyan
    This document is a problem set from a Massachusetts Institute of Technology course. It contains 6 problems involving organic synthesis reactions and mechanisms. The problems include proposing syntheses using the Robinson annulation, writing products of reactions, identifying intermediates in a transformation, completing a synthetic sequence, providing mechanisms for transformations, and providing syntheses for given products.

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    Problem Set #8: Massachusetts Institute of Technology 5.13, Fall 2006

    Uploaded by

    Karthikeyan
    47 views3 pages
    This document is a problem set from a Massachusetts Institute of Technology course. It contains 6 problems involving organic synthesis reactions and mechanisms. The problems include proposing syntheses using the Robinson annulation, writing products of reactions, identifying intermediates in a transformation, completing a synthetic sequence, providing mechanisms for transformations, and providing syntheses for given products.

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    IOC 12

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    This document is a problem set from a Massachusetts Institute of Technology course. It contains 6 problems involving organic synthesis reactions and mechanisms. The problems include proposing syntheses using the Robinson annulation, writing products of reactions, identifying intermediates in a transformation, completing a synthetic sequence, providing mechanisms for transformations, and providing syntheses for given products.

    Copyright:

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

    Problem Set #8: Massachusetts Institute of Technology 5.13, Fall 2006

    Uploaded by

    Karthikeyan
    This document is a problem set from a Massachusetts Institute of Technology course. It contains 6 problems involving organic synthesis reactions and mechanisms. The problems include proposing syntheses using the Robinson annulation, writing products of reactions, identifying intermediates in a transformation, completing a synthetic sequence, providing mechanisms for transformations, and providing syntheses for given products.

    Copyright:

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

    Massachusetts Institute of Technology 5.

    13, Fall 2006

    Problem Set #8
    Due: December 4, 2006, 12:00 PM

    1. Propose a one-step synthesis for the following compounds using the


    Robinson annulation.

    Me
    OCH3
    a)
    O

    O
    b)

    CO 2Et

    2. Write the products for the following reactions.

    CH3 NaOCH3
    O
    a) H2C
    CH3OH, D
    O

    O
    1. LDA
    b) 2. HC
    CH3

    3. Identify the intermediates A and B in the transformation below and show how
    they are formed (mechanism).

    CH3 CH3
    O O -OH
    NaOEt KOtBu
    A B H3 C
    EtO H Et H2O

    O H
    H excess

    Massachusetts Institute of Technology 5.13, Fall 2006

    4. Write reagents (a, b, c, d) where they have been omitted from the following
    synthetic sequence. Each letter may correspond to one or more reaction steops.
    This sequence is the beginning of a synthesis of germanicol, a naturally
    occurring triterpene.

    Me Me

    Me Me Me

    H Me
    HO
    H
    Me Me
    Germanicol

    Me O
    a Me H+, ethylene glycol H3 C
    H3C
    O O
    O O
    O
    CH3 O
    b

    Me Me Me O Me Me O
    O O c 1. Li, NH3
    H O O
    2. CH3I
    Me O O O
    Me MeH Me MeH Me

    Me
    O O
    H
    Me O
    Me MeH

    Massachusetts Institute of Technology 5.13, Fall 2006

    5. Provide a mechanism for each of the following transformations.

    O O

    NaOMe (1 eq.)

    a) O Ph
    MeOH
    Ph O

    Me
    H N
    N Me N
    N cat. H+
    b)
    O Me
    Me

    6. Provide a synthesis for each of the following products.

    O O O O
    O O
    a) Me H b) c) d)
    Me N Me
    H Ph Me
    Ph Me

    MeOH EtOH PrOH

    OH
    Ph OH

    starting materials

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