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    52Ex2X13 PDF

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    This document appears to be the cover page for a chemistry exam consisting of 8 pages and 120 total points. It provides instructions for taking the exam, including that notes and electronic devices are not permitted, and that the exam is administered under the Dartmouth College Honor Principle. The student has 2 hours to complete the exam. The cover page also includes a table to record points earned for each question on the exam.

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    52Ex2X13 PDF

    Uploaded by

    edece
    73 views9 pages
    This document appears to be the cover page for a chemistry exam consisting of 8 pages and 120 total points. It provides instructions for taking the exam, including that notes and electronic devices are not permitted, and that the exam is administered under the Dartmouth College Honor Principle. The student has 2 hours to complete the exam. The cover page also includes a table to record points earned for each question on the exam.

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    This document appears to be the cover page for a chemistry exam consisting of 8 pages and 120 total points. It provides instructions for taking the exam, including that notes and electronic devices are not permitted, and that the exam is administered under the Dartmouth College Honor Principle. The student has 2 hours to complete the exam. The cover page also includes a table to record points earned for each question on the exam.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    73 views9 pages

    52Ex2X13 PDF

    Uploaded by

    edece
    This document appears to be the cover page for a chemistry exam consisting of 8 pages and 120 total points. It provides instructions for taking the exam, including that notes and electronic devices are not permitted, and that the exam is administered under the Dartmouth College Honor Principle. The student has 2 hours to complete the exam. The cover page also includes a table to record points earned for each question on the exam.

    Copyright:

    © All Rights Reserved
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    Download as pdf or txt
    of 9

    Name_____________________________________

    Exam 2
    Chemistry 52
    July 25, 2013

    Do not open or begin this exam until instructed. This exam consists of 8 pages plus the cover
    page and 1 scrap page. Before starting the exam, check to make sure that you have all of the
    pages. The exam has a total of 120 points and includes 13 questions. Only legible answers
    written on the exam will be considered for grading. All pertinent information needed for the
    exam is given. Notes, textbooks, and electronic communication devices are not permitted. This
    exam is administered under the Dartmouth College Honor Principle. You have 2 hours to
    complete the exam.

    Use your time wisely.

    Page Number Value Points Awarded


    1 16

    2 17

    3 22

    4 12

    5 20

    6 13

    7 10

    8 10

    Total 120
    1. (6 points, 3 each) Provide an IUPAC accepted name for each of the following compounds.
    O O

    2. (6 points, 2 each) Provide a representative compound for each of the following functional
    groups.
    hydrazone cyanohydrin lactone

    3. (4 points) Aramids are aromatic polyamides. As a class, they can be spun into heat-resistant,
    strong fibers. Kevlar is an aramid used in body armor fabric. Flame-resistant clothing can
    also be made from aramids. Below is an image that emphasizes the hydrogen-bonding
    between the polymer chains of an aramid. What monomers could be used to prepare this
    polymer? (Image from https://sites.google.com/site/aromaticpolyamides/.)

    1
    4. (6 points, 3 each) For each set of compounds, rank from least basic to most basic. Place
    your final answer in the box.

    5. (3 points) List the following compound in order of increasing reactivity toward nucleophilic
    acyl substitution. Place your final answer in the box.

    6. (20 points, 4 each) Provide the main organic product of each of the following reactions.

    2
    7. (10 points) Sodium valproate is used in the treatment of epilepsy. Propose a synthesis from
    1-butanol and any other reagents you need. As always, if you elect to use organometallic
    reagents or ylides, you must show how they are prepared.

    3
    8. (12 point, 2 each) Choose the best reagent(s) from the list provided for carrying out the
    following transformations. Place the corresponding letter in the box over the reaction arrow.

    a. (Ph)2CuLi, ether
    b. NaBH4, ethanol
    c. 1) CH3MgBr, ether 2) H3O+
    d. 1) LiAlH4, THF 2) H3O+
    e. (CH3)2CuLi, ether
    f. 1) 1 eq. DIBAL, toluene, -78 C 2) H3O+
    g. 1) Ph2CHMgBr, ether 2) H3O+
    h. 1) PhMgBr, ether 2) H3O+

    4
    9. (20 points, 5 each) Complete the following short syntheses by providing reagents over arrows
    and intermediate compounds in the boxes. Excluding workup steps, most can be completed
    in two steps.

    O O
    NH2

    5
    10. (3 points) Which spectroscopic technique would you use to distinguish between the
    following molecules? Briefly explain what differences you would expect to see.

    11. (10 points) Provide a complete electron pushing mechanism for the following. Be sure to
    include any by-products as they are formed and show arrows for every bond change. Do not
    combine steps!

    6
    12. (10 points) Provide the necessary sequence of reagents to achieve the following
    transformation. You may use any additional reagents you need. As always, if you elect to
    use organometallic reagents or ylides, you must show how they are prepared. You may find
    a Wittig reaction to be a useful step in this conversion. Show the intermediate compounds in
    your synthesis if you wish to receive partial credit.

    7
    13. (10 points) Provide a complete electron pushing mechanism for the following reaction using
    only the reagents provided. Be sure to include any by-products as they are formed and show
    arrows for every bond change. Do not combine steps!

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