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    CHE 232 Test 1

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    moatlhodi
    This document contains a 20-question quiz on organic chemistry concepts related to structure and functional groups. The questions cover topics such as naming organic compounds, identifying hybridization of carbon atoms, determining number of sigma bonds, drawing Newman projections, describing reaction mechanisms, and predicting products of reactions involving alkenes, alkynes, halogens and other functional groups. The document also provides multiple choice answers for the questions in Section A and outlines longer form questions testing additional concepts in Section B.

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    CHE 232 Test 1

    Uploaded by

    moatlhodi
    84 views11 pages
    This document contains a 20-question quiz on organic chemistry concepts related to structure and functional groups. The questions cover topics such as naming organic compounds, identifying hybridization of carbon atoms, determining number of sigma bonds, drawing Newman projections, describing reaction mechanisms, and predicting products of reactions involving alkenes, alkynes, halogens and other functional groups. The document also provides multiple choice answers for the questions in Section A and outlines longer form questions testing additional concepts in Section B.

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    CHE 232 Test 1

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    This document contains a 20-question quiz on organic chemistry concepts related to structure and functional groups. The questions cover topics such as naming organic compounds, identifying hybridization of carbon atoms, determining number of sigma bonds, drawing Newman projections, describing reaction mechanisms, and predicting products of reactions involving alkenes, alkynes, halogens and other functional groups. The document also provides multiple choice answers for the questions in Section A and outlines longer form questions testing additional concepts in Section B.

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

    CHE 232 Test 1

    Uploaded by

    moatlhodi
    This document contains a 20-question quiz on organic chemistry concepts related to structure and functional groups. The questions cover topics such as naming organic compounds, identifying hybridization of carbon atoms, determining number of sigma bonds, drawing Newman projections, describing reaction mechanisms, and predicting products of reactions involving alkenes, alkynes, halogens and other functional groups. The document also provides multiple choice answers for the questions in Section A and outlines longer form questions testing additional concepts in Section B.

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    © All Rights Reserved
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    of 11

    CHE 232 STRUCTURE AND SURVEY OF FUNCTIONAL GROUPS I

    (0RGANIC CHEMISTRY)
    QUESTIONS AND SOLUTIONS

    Section A
    ANSWER ALL QUESTIONS (each question is worth 2 marks)

    1. For the following structure there are …….1……..2 and ……..3 carbons

    A. 3, 4, 1
    B. 3, 3, 2
    C. 3, 2, 3
    D. 2, 3, 3

    2. What are the hybridizations of the carbons X, Y and Z?

    A. sp3, sp, sp
    B. sp2, sp, sp3
    C. sp2, sp, sp
    D. sp3, sp2, sp

    3. How many sigma bonds are present in the following molecule?

    1
    4. What is the IUPAC name of the following compound?

    A. 3-Bromo-2-hydroxypentane B. 2-Hydroxy-3-bromopentane

    C. 3-Bromopentan-2-ol D. 3-Bromopentan-4-ol

    5. Which of the following alkanes will have the highest boiling point?

    A. Pentane B. 2,2-dimethylbutane C. 2-methylpentane D. hexane

    6. What is the molecular formula of a hydrocarbon that has one triple bond, two double
    bonds, one ring and 32 carbon atoms?

    A. C32H62
    B. C32H60
    C. C32H58
    D. C32H56

    7. The eclipsed conformation of n-butane viewed along the C2/C3 bond has high energies
    because of:

    A. Steric strain
    B. Angle strain
    C. Torsional strain
    D. Both steric strain and torsional strain

    8. Which of the following Newman projection formulas represents 2,5-dimethylhexane?

    2
    9. Which of the following compounds can exist as cis-trans isomers?

    A. I and II B. I and IV C. I and III D . II and III

    10. How many monochlorination product(s) are possible in the reaction of the alkane shown
    below with chlorine in the presence of light?

    A.. 4 B. 5 C. 6 D. 7

    11. According to the Cahn-Ingold-Prelog convention, which priority ranking is correct for the
    following sets of groups?

    A. NH2 > OCH3 >CH3 >H C. H > OCH3 >CH3 > NH2

    B. OCH3 > NH2 > CH3 > H D. OCH3 > CH3 > NH2 > H

    12. The bromination of cyclopentene gives:

    A. cis-1,2-dibromocyclopentane
    B. trans-1,2-dibromopentane
    C. 1,1-dibromocyclopentane
    D. trans-1,2-dibromocyclopentane

    13. The relationship between the structures below is best described by which term?

    3
    A. Tautomers
    B. Resonance structures
    C. Conformational isomers
    D. Stereoiosmers

    14. Which one of the following schemes showing the flow of electrons from reagent forming
    products is not correct?

    15. The following reaction occurs in the formation of chloroethane from ethane by its
    reaction with chlorine in the presence of light. In which step does this reaction occur?

    CH3CH3 + Cl CH3CH2 + HCl

    A. Initiation
    B. Propagation
    C. Termination
    D. Both Termination and Initiation

    16. Hydrogenation of 1,2-dimethylcyclohexene in the presence of a platinum catalyst will


    give:

    A. Trans-1,2-dimethylcyclohexane
    B. Cis-1,2-dimethylcyclohexane

    4
    C. 1,2-Dimethylhexane
    D. 1,3-Dimethylhexane

    17. Which of the following reagents will NOT yield the given product in the reaction shown
    below?

    18. Addition of one equivalent of HBr to but-2-yne will produce

    A. 2,2-dibromobutane
    B. cis-2-bromobut-2-ene
    C. trans-2-bromobut-2-ene
    D. cis and trans-2-bromobut-2-ene
    19. Which one of the hydrogen atoms in the following compound is most acidic?

    A. Hydrogen atom attached to C-1


    B. Hydrogen atom attached to C-3
    C. Hydrogen atom attached to C-5
    D. Hydrogen atom attached to C-2
    20. Which of the following compounds will be produced from the alkyne hydration
    reaction shown below?

    5
    SECTION B
    EACH QUESTION IS WORTH 20 MARKS. ANSWER ALL QUESTIONS

    Question 1

    (i) Give the systematic names for the following compounds. Include stereochemistry
    where applicable. [6 marks]

    (ii) Draw the structures of compounds corresponding to the following systematic names.
    [4 marks]
    a. 4-Hydroxy-2-methylpentanoic acid

    …………………………………………………………………………………………

    6
    b. 7-Methyloct-1-en-4-yne

    ………………………………………………………………………………………..

    (iii) Assign E and Z configuration for the compounds shown below. [8 marks]

    (iv) Write a balanced equation for the complete combustion of n-butane. [2 marks]

    Question Two

    (i) For rotation about C1-C2 bond of 2,2-dimethylpropane draw the Newman projections
    of the staggered and eclipsed conformations. [4 marks] [hint: there is only one of
    each]

    7
    (ii) Give the product for the reaction below and hence draw the chair conformations of
    the product indicating the most stable conformational structure. [4 marks]

    (iii) Give the structures of the alkenes that will yield the indicated products in each of the
    following reactions. [6
    marks]

    (iv) Give the structures of the major products in each of the following reactions. [6
    marks]

    8
    Question Three

    (i) Draw proper curved arrows to complete the reaction mechanism shown below and
    give structures of two possible termination products. [6 marks]

    Structures of two termination products: Combination of any two radicals

    9
    (ii) Give the structures of the missing products or reagents in the reaction scheme shown
    below.[10 marks]

    (iii) An alkyne with molecular formula C5H8 is treated with excess HBr and two different
    products are obtained each of which has molecular formula C5H10Br2.
    (a) Give the structure of the starting alkyne.

    …………………………………………………………………[1 mark]

    (b) Give the structures of the two products.

    10
    ……………………………………………………………….[3 marks]

    11

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