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  • Chem 112A F11 Homework 3

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    Shyam Bhakta
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    This document outlines a problem set assignment for a chemistry class that is due on October 27th, 2011. It includes 7 multi-part questions requiring the student to: 1) classify compounds as chiral or achiral and assign stereocenters, 2) identify stereocenters in a natural product, 3) draw stereoisomers and assign stereocenters, 4) propose syntheses of alcohols from alkenes, 5) draw chair conformations of cyclohexanes, 6) rank C-H bond strengths, and 7) provide reaction mechanisms. The student is encouraged to work in small groups on the assignment.

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    This document outlines a problem set assignment for a chemistry class that is due on October 27th, 2011. It includes 7 multi-part questions requiring the student to: 1) classify compounds as chiral or achiral and assign stereocenters, 2) identify stereocenters in a natural product, 3) draw stereoisomers and assign stereocenters, 4) propose syntheses of alcohols from alkenes, 5) draw chair conformations of cyclohexanes, 6) rank C-H bond strengths, and 7) provide reaction mechanisms. The student is encouraged to work in small groups on the assignment.

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    © All Rights Reserved
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    19 views6 pages

    Chem 112A F11 Homework 3

    Uploaded by

    Shyam Bhakta
    This document outlines a problem set assignment for a chemistry class that is due on October 27th, 2011. It includes 7 multi-part questions requiring the student to: 1) classify compounds as chiral or achiral and assign stereocenters, 2) identify stereocenters in a natural product, 3) draw stereoisomers and assign stereocenters, 4) propose syntheses of alcohols from alkenes, 5) draw chair conformations of cyclohexanes, 6) rank C-H bond strengths, and 7) provide reaction mechanisms. The student is encouraged to work in small groups on the assignment.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    of 6

    Due by 5pm on Oct. 27th, 2011. You are encouraged to work in small groups for this assignment.

    Write your name AND your lab section on the problem set before submitting it.
    1. Classify each of the following compounds as chiral or achiral. If they are chiral, assign all stereocenters in the provided drawing as (R) or (S) and draw the corresponding enantiomer. a.
    Br

    Chem 112A, Fall 2011 - Problem Set 3

    f.

    O CH3 O

    O CH3

    b.

    Cl

    g.
    Cl

    CH3

    Br O

    c.

    O CH3

    h.

    HO OH

    OH

    d.

    i.

    OH OH OH

    e.

    j.

    2. Taxol is a complex natural product obtained originally from the Pacific yew tree. It has been prescribed widely as a treatment for breast and ovarian cancers. Identify all of the stereogenic centers in this molecule and label them as (R) or (S).

    O O NH O O O O O O OH

    HO

    O O O

    O O

    HO

    3. Draw all possible stereoisomers of the following compounds and then remove any duplicates. Label the remaining structures as chiral or achiral. Finally, assign the stereocenters in the chiral compounds as (R) or (S).

    a.

    Cl

    CH3

    b.

    Cl Cl

    c.
    H3C

    CH3 OH

    d.

    Br

    Cl OH

    e.

    HO2C

    OH OH OH

    CO2H

    4. Show how each of the following alcohol or diol products can be synthesized from an alkene precursor. For each answer, provide the structure of the starting material that you would use and the reagents that you would need to carry out the transformation. a.
    OH

    b.

    Ph OH

    OH

    c.

    OH

    d.

    OH OH

    e.

    f.

    OH Ph

    Ph

    OH OH

    g.

    Ph

    CH3

    OH

    h.

    H3C OH Ph Br

    CH3

    i.

    H3C OH Ph Br

    CH3

    5. Provide clear and accurate chair diagrams for each of the following substituted cyclohexanes. Be sure to flip the chairs to determine the lowest energy conformation.

    a.
    CH3

    CH3

    H3C CH3

    b.
    CH3

    CH3

    c.

    H3C

    CH3

    d.

    H3C H3C

    CH3 CH3

    CH3

    6. Rank the following compounds by the strength of the indicated C-H bonds. Use 1 to indicate the weakest bond and 6 to indicate the strongest.
    H H H3C H CH3 N H H O H

    Cl

    Cl

    7. Provide detailed, arrow-pushing mechanisms for each of the following reactions:


    O O O 1. O3 2. PPh3 O Ph O O

    a. Ph

    Ph

    b. Ph

    O O O

    Ph

    OsO4 THF / H2O

    O Ph O

    OH OH O

    Ph

    c.

    NH2 methacrylamide

    AIBN heat

    poly(methacrylamide) provide structure and mechanism

    O CH3 Ph + Br2 O

    O O

    Ph Br + HBr

    d.

    heat

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