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    Fall 2014 Exam 3

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    alfred
    This document is the instructions for Exam 3 in Chemistry 2210 during the Fall 2014 semester. It consists of 40 multiple choice and short answer problems testing organic chemistry concepts like functional groups, stereochemistry, resonance structures, reaction mechanisms, and multi-step syntheses. Students are instructed to show all work for problems and that no late submissions will be accepted. The exam is due by the end of class on November 20, 2014.

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    Fall 2014 Exam 3

    Uploaded by

    alfred
    19 views11 pages
    This document is the instructions for Exam 3 in Chemistry 2210 during the Fall 2014 semester. It consists of 40 multiple choice and short answer problems testing organic chemistry concepts like functional groups, stereochemistry, resonance structures, reaction mechanisms, and multi-step syntheses. Students are instructed to show all work for problems and that no late submissions will be accepted. The exam is due by the end of class on November 20, 2014.

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    This document is the instructions for Exam 3 in Chemistry 2210 during the Fall 2014 semester. It consists of 40 multiple choice and short answer problems testing organic chemistry concepts like functional groups, stereochemistry, resonance structures, reaction mechanisms, and multi-step syntheses. Students are instructed to show all work for problems and that no late submissions will be accepted. The exam is due by the end of class on November 20, 2014.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    19 views11 pages

    Fall 2014 Exam 3

    Uploaded by

    alfred
    This document is the instructions for Exam 3 in Chemistry 2210 during the Fall 2014 semester. It consists of 40 multiple choice and short answer problems testing organic chemistry concepts like functional groups, stereochemistry, resonance structures, reaction mechanisms, and multi-step syntheses. Students are instructed to show all work for problems and that no late submissions will be accepted. The exam is due by the end of class on November 20, 2014.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 11

    Chemistry 2210 – Fall 2014

    Exam 3
    Name________________________________________________________

    Instructions: There is no penalty for guessing (attempt all problems). For all problems there is no
    partial credit, every bond must have the proper regiochemistry and stereochemistry
    where needed. The exam is due by the end of class on November 20. No late
    submissions will be accepted.
    Problems:
    1) Explain why : NF 3 is a weaker base than : NH3. 1)

    2) 2-Propanol is shown below. Draw the structure of its conjugate base. 2)

    (CH3)2CHOH

    3) How many asymmetric centers are present in the compound below? 3)

    4) Provide the structure of (R)-4-octanol. Be careful to indicate proper stereochemistry. 4)

    5) Provide a careful structure for (2R,3S)-2,3-dibromohexane. 5)

    6) Which of the following terms best describes the pair of compounds shown: 6)
    enantiomers, diastereomers, or the same compound?

    1
    7) Which of the following terms best describes the pair of compounds shown: 7)
    enantiomers, diastereomers, or the same compound?

    8) Draw the structure of any diastereomer of (2R,3S)-dichloropentane. Take particular care 8)


    to indicate three-dimensional stereochemistry detail properly.

    9) Is the molecule shown chiral? Is it a meso compound? 9)

    10) Is the molecule shown chiral? Is it a meso compound? 10)

    11) Assign an R or S configurational label to each asymmetric center in the molecule below. 11)

    2
    12) Draw an acceptable structure for 3-sec-butyl-1-heptyne. 12)

    13) Provide the systematic name of the compound shown. 13)

    14) Provide the structure of the major organic product of the following reaction. 14)

    15) Provide the major organic product in the reaction below. 15)

    16) Provide the major organic product in the reaction below. 16)

    3
    17) Provide the major organic product in the reaction below. 17)

    18) Provide the structure of the major organic produt that results when 2-butyne is treated 18)
    with 2 equivalents of HCl.

    19) Provide the structure of the major organic produt that results when 2-butyne is treated 19)
    with HgSO4/H2SO4 in water

    20) Provide the structure of the major organic product of the following reaction. 20)

    21) Provide the major organic product in the reaction below. 21)

    4
    22) Provide the major organic product in the reaction below. 22)

    23) Complete the following reaction. 23)

    Na, NH3
    3-hexyne

    24) Provide the structure of the major organic product of the following reaction. 24)

    25) Provide the structure of the major organic product of the following reaction. 25)

    5
    26) Complete the following tree of reactions by giving the major products. 26)

    27) Provide the sequence of reagents that are needed to accomplish the multistep synthesis 27)
    below.

    28) Provide the sequence of reagents that are needed to accomplish the multistep synthesis 28)
    below.

    6
    29) Draw two other resonance contributors for the following compound: 29)

    30) Draw the important resonance contributing forms for the structure shown below. 30)

    31) Draw the structure of the major product which results when the diene shown is treated 31)
    with HBr at 40°C.

    32) Draw the structure of the major product which results when the diene shown is treated 32)
    with HBr at -80°C.

    7
    33) Provide the major organic product. 33)

    34) Provide the major organic product. 34)

    35) Draw (Z)-1,3-hexadiene in its s-trans conformation. 35)

    36) What is the product of the following Diels-Alder reaction? 36)

    8
    37) What diene and what dieneophile could be used to prepare the following? 37)

    38) Provide the structure of the major organic product in the following reaction. 38)

    39) Provide the structure of the major organic product in the following reaction. 39)

    40) Draw the s-trans conformation of (2E,4Z)-4-methyl-2,4,-heptadiene. 40)

    9
    Mechanism and Synthesis:
    1) Provide a detailed, stepwise mechanism for the reaction below. 1)
    (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

    2) Describe a sequence of reactions by which the compound shown below can be straightforwardly prepared
    from acetylene. You need to only state the reagents in the proper order.

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