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    Chapter 4 Practice: Problems 1,2-Dichloroethane

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    The document describes problems involving the conformations of various organic molecules including 1,2-dichloroethane, 2-methylbutane, substituted cyclohexanes, and biomolecules like (-)-menthol and D-pinitol. It asks students to draw Newman projections and chair conformations of the different molecules, identify stable and unstable conformations, and explain observations about substituent preferences.

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    Chapter 4 Practice: Problems 1,2-Dichloroethane

    Uploaded by

    cwod
    156 views8 pages
    The document describes problems involving the conformations of various organic molecules including 1,2-dichloroethane, 2-methylbutane, substituted cyclohexanes, and biomolecules like (-)-menthol and D-pinitol. It asks students to draw Newman projections and chair conformations of the different molecules, identify stable and unstable conformations, and explain observations about substituent preferences.

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    Chapter 4 practice 2210

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    The document describes problems involving the conformations of various organic molecules including 1,2-dichloroethane, 2-methylbutane, substituted cyclohexanes, and biomolecules like (-)-menthol and D-pinitol. It asks students to draw Newman projections and chair conformations of the different molecules, identify stable and unstable conformations, and explain observations about substituent preferences.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    156 views8 pages

    Chapter 4 Practice: Problems 1,2-Dichloroethane

    Uploaded by

    cwod
    The document describes problems involving the conformations of various organic molecules including 1,2-dichloroethane, 2-methylbutane, substituted cyclohexanes, and biomolecules like (-)-menthol and D-pinitol. It asks students to draw Newman projections and chair conformations of the different molecules, identify stable and unstable conformations, and explain observations about substituent preferences.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 8

    Chapter 4 Practice

    Problems

    1,2-dichloroethane
    Experiments have shown that for 1,2-dichloroethane, ClCH2CH2Cl, in carbon tetrachloride solution at 25° C,
    70% of the molecules are in the anti and 30% are in the gauche conformation.

    1. Refer to 1,2-dichloroethane. Draw a Newman projection of the anti conformation of 1,2-dichloroethane.


    2. Refer to 1,2-dichloroethane. Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.
    3. Refer to 1,2-dichloroethane. Draw a Newman projection of the least stable conformation of
    1,2-dichloroethane.

    2-methylbutane
    Consider the conformations of 2-methylbutane shown below to answer the following questions.

    4. Refer to 2-methylbutane. Which of the structures has two gauche interactions?


    5. Refer to 2-methylbutane. Which of the structures represents the most stable conformation of 2-methylbutane?
    6. Refer to 2-methylbutane. Which of the structures represents the least stable conformation of 2-methylbutane?

    Matching 4-1
    MATCH the Newman projection for the conformation of 2-methylbutane to the indicated position on the
    potential energy diagram and place the letter corresponding to the correct projection in the blank.
    7. Refer to Matching 4-1. This energy maximum corresponds to the Newman projection labeled __________.
    8. Refer to Matching 4-1. This energy minimum corresponds to the Newman projection labeled __________.
    9. Refer to Matching 4-1. This energy maximum corresponds to the Newman projection labeled __________.
    10. Refer to Matching 4-1. This energy minimum corresponds to the Newman projection labeled __________.

    Structure 4-1
    Refer to the structure below to answer the following questions:

    11. Refer to Structure 4-1. Which of the labeled bonds in the structure are equatorial bonds?
    12. Refer to Structure 4-1. Which of the labeled bonds is trans to bond b?
    13. Refer to Structure 4-1. Which bonds have a 1,3-diaxial interaction with each other?
    14. For each substituted cyclohexane, draw its ring-flip isomer. Circle the most stable conformation.

    15. For each substituted cyclohexane, draw its ring-flip isomer. Circle the most stable conformation.

    16. For each substituted cyclohexane, draw its ring-flip isomer. Circle the most stable conformation.
    17. In general, 5-alkyl substituents in 1,3-dioxane exhibit a smaller equatorial preference than they do in
    cyclohexane. To what might you attribute this observation?

    18. For each pair of molecules, circle the most stable.

    19. For each pair of molecules, circle the most stable.

    20. (-)-Menthol can be isolated from the peppermint plant and is responsible for the characteristic flavor and taste
    of peppermint. The structure of (-)-menthol is:
    On the chair template provided below, draw the two chair conformations that are in equilibrium for
    (-)-menthol.

    21. D-Pinitol is an interesting hexahydroxy cyclohexane, whose structure is shown below.

    On the templates provided, draw the two chair conformations that are in equilibrium for D-pinitol. Circle the
    most stable conformation.
    Chapter 4 Practice
    Answer Section

    PROBLEM

    1. ANS:

    PTS: 1
    2. ANS:

    PTS: 1
    3. ANS:

    PTS: 1
    4. ANS:
    C.

    PTS: 1
    5. ANS:
    A.

    PTS: 1
    6. ANS:
    B.

    PTS: 1
    7. ANS:
    D.

    PTS: 1
    8. ANS:
    A.

    PTS: 1
    9. ANS:
    B.

    PTS: 1
    10. ANS:
    C.

    PTS: 1
    11. ANS:
    a and d

    PTS: 1
    12. ANS:
    e

    PTS: 1
    13. ANS:
    b and c

    PTS: 1
    14. ANS:

    PTS: 1
    15. ANS:

    PTS: 1
    16. ANS:
    PTS: 1
    17. ANS:
    The 5-alkyl substituted dioxanes do not suffer from 1,3-diaxial interactions since there are no hydrogens that
    are axial to the 5-substituent. Hence, the axial conformation is more stable in 5-substituted 1,3-dioxanes than
    it is in substituted cyclohexanes.

    PTS: 1
    18. ANS:

    PTS: 1
    19. ANS:

    PTS: 1
    20. ANS:

    PTS: 1
    21. ANS:
    PTS: 1

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