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Following are the structural formulas and names of four bicycloalkanes. Write the molecular formula of each compound. Which of these compounds are constitutional isomers?

Short Answer

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(1) Bicyclo[3.2.0]heptane (2) Bicyclo[2.2.2]octane (3) Bicyclo[3.3.1]nonane (4) Bicyclo[4.4.0]decane Following the step by step solution: Step 1: Analyze the structural formulas (1) Bicyclo[3.2.0]heptane: 7 carbon atoms and 12 hydrogen atoms (2) Bicyclo[2.2.2]octane: 8 carbon atoms and 14 hydrogen atoms (3) Bicyclo[3.3.1]nonane: 9 carbon atoms and 16 hydrogen atoms (4) Bicyclo[4.4.0]decane: 10 carbon atoms and 18 hydrogen atoms Step 2: Write the molecular formula of each compound (1) Bicyclo[3.2.0]heptane: C7H12 (2) Bicyclo[2.2.2]octane: C8H14 (3) Bicyclo[3.3.1]nonane: C9H16 (4) Bicyclo[4.4.0]decane: C10H18 Step 3: Identify the constitutional isomers Comparing the molecular formulas, we can see that none of the bicycloalkanes have the same molecular formula. Therefore, there are no constitutional isomers among the given compounds.

Step by step solution

01

Analyze the structural formulas

Examine the structural formulas of the bicycloalkanes and count the number of carbon (C) and hydrogen (H) atoms in each compound.
02

Write the molecular formula of each compound

After determining the number of carbon and hydrogen atoms in each bicycloalkane, write the molecular formula for each of the compounds as follows: C_xH_y where x represents the number of carbon atoms and y represents the number of hydrogen atoms.
03

Identify the constitutional isomers

Compare the molecular formulas of all four bicycloalkanes. Two or more compounds with the same molecular formula but different arrangements of the atoms are constitutional isomers. Identify these compounds, if there are any, among the bicycloalkanes provided.

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Most popular questions from this chapter

\(1,2,3,4,5,6\)-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans3,6-hexachlorocyclohexane. (a) Draw a structural formula for \(1,2,3,4,5,6\)-hexachlorocyclohexane disregarding, for the moment, the existence of cis,trans isomerism. What is the molecular formula of this compound? (b) Using a planar hexagon representation for the cyclohexane ring, draw a structural formula for lindane. (c) Draw a chair conformation for lindane and label which chlorine atoms are axial and which are equatorial. (d) Draw the alternative chair conformation of lindane and again label which chlorine atoms are axial and which are equatorial. (e) Which of the alternative chair conformations of lindane is more stable? Explain.

Draw the alternative chair conformations for the cis and trans isomers of 1,2 -dimethylcyclohexane, 1,3 -dimethylcyclohexane, and 1,4 -dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?

What generalization can you make about the densities of alkanes relative to the density of water?

When cyclohexane is substituted by an ethynyl group, \(-\mathrm{C} \equiv \mathrm{CH}\), the energy difference between axial and equatorial conformations is only \(1.7 \mathrm{~kJ}(0.41 \mathrm{kcal}) / \mathrm{mol}\). Compare the conformational equilibrium for methylcyclohexane with that for ethynylcyclohexane and account for the difference between the two.

Following are the alternative chair conformations for trans-1,2-dimethylcyclohexane. (a) Estimate the difference in free energy between these two conformations. (b) Given your value in (a), calculate the percent of each chair present in an equilibrium mixture of the two at \(25^{\circ} \mathrm{C}\).

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