Scribd Logo
Upload

Welcome to Scribd!

  • 130 views

    This Study Resource Was: Department of Chemistry, IIT Bombay

    Uploaded by

    Sandipan Saha
    This document appears to be an exam for an organic chemistry course. It contains 10 questions testing students' understanding of organic chemistry concepts like reaction mechanisms, conformational analysis, stereochemistry, aromaticity, molecular orbital theory and more. Students are asked to draw structures, suggest reaction steps, assign stereochemistry, identify symmetry elements and calculate energy differences. The exam is worth a total of 25 marks and students are given 2 hours to complete it under exam conditions.

    Copyright:

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

    This Study Resource Was: Department of Chemistry, IIT Bombay

    Uploaded by

    Sandipan Saha
    130 views2 pages
    This document appears to be an exam for an organic chemistry course. It contains 10 questions testing students' understanding of organic chemistry concepts like reaction mechanisms, conformational analysis, stereochemistry, aromaticity, molecular orbital theory and more. Students are asked to draw structures, suggest reaction steps, assign stereochemistry, identify symmetry elements and calculate energy differences. The exam is worth a total of 25 marks and students are given 2 hours to complete it under exam conditions.

    Original Title

    CH105_Exam_2014_Fall.pdf

    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 appears to be an exam for an organic chemistry course. It contains 10 questions testing students' understanding of organic chemistry concepts like reaction mechanisms, conformational analysis, stereochemistry, aromaticity, molecular orbital theory and more. Students are asked to draw structures, suggest reaction steps, assign stereochemistry, identify symmetry elements and calculate energy differences. The exam is worth a total of 25 marks and students are given 2 hours to complete it under exam conditions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    130 views2 pages

    This Study Resource Was: Department of Chemistry, IIT Bombay

    Uploaded by

    Sandipan Saha
    This document appears to be an exam for an organic chemistry course. It contains 10 questions testing students' understanding of organic chemistry concepts like reaction mechanisms, conformational analysis, stereochemistry, aromaticity, molecular orbital theory and more. Students are asked to draw structures, suggest reaction steps, assign stereochemistry, identify symmetry elements and calculate energy differences. The exam is worth a total of 25 marks and students are given 2 hours to complete it under exam conditions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 2

    Department of Chemistry, IIT Bombay

    CH 105:Organic Chemistry
    End-Semester Examination
    Marks: 25 Time: 2 hours August 23, 2014
    All answers must be written using blue/blackpen. Answers written with pencil will not be corrected.

    1. Suggest a plausible step-wise mechanism for the following reaction. Clearly show all the arrow-pushing.
    (2 marks)

    2. How will you do the following conversion? You can use any other simple reagents/reactants. Your
    reaction sequence should not contain more than five steps. Show the structures of the intermediate
    compounds. Do not draw the mechanisms of the steps involved. (3 marks)

    m
    er as
    co
    eH w
    o.
    rs e
    3. Consider the following transformations. (i) Draw the conformational structures of the starting materials
    ou urc
    A and D. (ii) Based on the conformational structures, explain the formation of the products in both the
    cases. Your answer should be explained with the help of arrows, clearly showing the mechanism. You
    are expected to show configuration of hydrogen atoms ONLY at the ring junctions and at the reaction
    centers. (3 marks)
    o
    aC s
    vi y re
    ed d
    ar stu
    sh is
    Th

    4. Draw Newman projections of all conformers for meso-2,3-dibromobutane. Using the values of gauche
    interactions given below, calculate the difference in the energy between the lowest energy and the next
    higher energy conformer.
    Gauche interactions: Me/Me = 0.9 kcal mol−1, Me/Br = 0.25 kcal mol−1, Br/Br = 0.75 kcal mol−1
    (3 marks)

    5. How many stereoisomers are possible for the compound (CH3CH=CH)2CH(OH)? Draw their structures
    using wedge formula. (2 marks)
    (Note: Marks will be awarded only if the first part is answered correctly)

    https://www.coursehero.com/file/44890006/CH105-Exam-2014-Fallpdf/ 1
    6. Assign the absolute configurations (R and S) for the following molecules. (2 marks)
    a) b)

    7. Identify and pictorially show (use dotted lines) the symmetry elements present for all stereoisomers of
    H(Cl)C=C=C=C(Cl)H (2 marks)

    8. Identify the following compounds as aromatic/non-aromatic/antiaromatic. (2 marks)


    a) b)

    9. Based on the analysis of the highest occupied molecular orbital (HOMO) (show picture) provide the

    m
    er as
    relative stereochemistry (cis/trans) of ring-junctionhydrogens in the product. Your answer should clearly
    explain the stereochemistry with the help of appropriate arrows. (3 marks)

    co
    eH w
    o.
    rs e
    ou urc
    o
    aC s

    10. The barrier for the following isomerization can be calculated as the energy difference between the
    vi y re

    reactant and a diradical transition state, as shown:


    ed d
    ar stu
    sh is
    Th

     
     
    Calculate the rotational barrier (in terms of α and β using the energies of the relevant molecular orbitals
    given below:
    1,3‐butadiene  ψ1= α+1.618β ψ2= α+0.618β
    allyl  ψ1= α+1.414β ψ2= α
    (3 marks)

    https://www.coursehero.com/file/44890006/CH105-Exam-2014-Fallpdf/ 2

    Powered by TCPDF (www.tcpdf.org)

    You might also like