Exam 4: Organic Compounds: Cycloalkanes and Their Stereochemistry

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Consider the following table. Consider the following table.   What is the approximate strain energy per CH<sub>2</sub> for cyclopropane? What is the approximate strain energy per CH2 for cyclopropane?

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B

What relationship exists between the following two structures? What relationship exists between the following two structures?    What relationship exists between the following two structures?

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C

Below are the two chair conformations of a 1,2,4-trimethylcyclohexane.Estimate the amount of 1,3-diaxial strain in each conformer and predict which conformer is most stable. Below are the two chair conformations of a 1,2,4-trimethylcyclohexane.Estimate the amount of 1,3-diaxial strain in each conformer and predict which conformer is most stable.

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    Conformer B is more stable than conformer A by 3.8 kJ/mol.     Conformer B is more stable than conformer A by 3.8 kJ/mol.
Conformer B is more stable than conformer A by 3.8 kJ/mol.

Exhibit 4-3 The following question(s) refer to the structure of camphor shown below. Exhibit 4-3 The following question(s) refer to the structure of camphor shown below.   -Refer to Exhibit 4-3.Camphor is an example of a: -Refer to Exhibit 4-3.Camphor is an example of a:

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Exhibit 4-2 For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation. -Refer to Exhibit 4-2. Exhibit 4-2 For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation. -Refer to Exhibit 4-2.

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Exhibit 4-4 Label each pair of compounds below as: -_____ Exhibit 4-4 Label each pair of compounds below as: -_____

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Exhibit 4-1 Refer to the structure below to answer the following question(s): Exhibit 4-1 Refer to the structure below to answer the following question(s):   -Refer to Exhibit 4-1.Which of the labeled bonds are trans to bond b? -Refer to Exhibit 4-1.Which of the labeled bonds are trans to bond b?

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Which of the following would produce the greatest amount of 1,3-diaxial strain when substituted for Cl in the following structure? Which of the following would produce the greatest amount of 1,3-diaxial strain when substituted for Cl in the following structure?

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Exhibit 4-2 For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation. -Refer to Exhibit 4-2. Exhibit 4-2 For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation. -Refer to Exhibit 4-2.

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In methylcyclohexane:

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Draw: 3,5-dicyclohexylnonane

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Draw: 3-cyclobutylpentane

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Exhibit 4-4 Label each pair of compounds below as: -_____ Exhibit 4-4 Label each pair of compounds below as: -_____

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Consider the two methyl groups indicated with letters in the following molecular model. Consider the two methyl groups indicated with letters in the following molecular model.   These two groups are: These two groups are:

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Exhibit 4-1 Refer to the structure below to answer the following question(s): Exhibit 4-1 Refer to the structure below to answer the following question(s):   -Refer to Exhibit 4-1.Which labeled bonds have a 1,3-diaxial interaction with each other? -Refer to Exhibit 4-1.Which labeled bonds have a 1,3-diaxial interaction with each other?

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Which of the following would have the smallest strain energy (kJ/mol)?

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Exhibit 4-4 Label each pair of compounds below as: -_____ Exhibit 4-4 Label each pair of compounds below as: -_____

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The two structures show below represent: The two structures show below represent:

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