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In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.

(a) Nonane or 3-methylheptane

(b) Octane or 2,3,4-trimethylpentane

(c) 2,3,5-trimethylhexane or nonane

Short Answer

Expert verified

(a) Nonane has higher boiling point than 3-methylheptane due to its higher molecular weight and linear structure.

(b) Octane has higher boiling point than 2,3,4-trimethylpentane because octane is a linear molecule while 2,3,4-trimethylpentane is branched molecule.

(c) Nonane has higher boiling point than 2,3,5-trimethylhexane due to its linear structure.

Step by step solution

01

Step-1. Explanation of part (a):

Higher the boiling point of the compound, less volatile will it be. As the number of carbon atoms or length of carbon chain increases, the boiling point also increases. This is due to increase in attractive forces between the molecules and it will take more energy to overcome that force of attraction, thereby increasing the boiling point. Branching in molecules decreases the boiling point. Nonane will have higher boiling point than 3-methylheptane due to its higher molecular weight and linear structure whereas 3-methylheptane is not linear.

02

Step-2. Explanation of part (b):

Branching in molecules decreases the boiling point of the molecule as when length of carbon chain increases, there occurs increase in the surface area of the compound. Increase of surface area increases the ability of molecules to attract each other. Branching in molecules decreases the surface area due to which boiling point decreases. Octane has higher boiling point than 2,3,4-trimethylheptane as octane is linear whereas 2,3,4-trimethylheptane is branched.

03

Step-3. Explanation of part (c):

Higher the boiling point of the compound, less volatile will it be. As the number of carbon atoms or length of carbon chain increases, the boiling point also increases. This is due to increase in attractive forces between the molecules and it will take more energy to overcome that force of attraction, thereby increasing the boiling point. Branching in molecules decreases the boiling point. Nonane will have higher boiling point than 2,3,5-trimethylhexane due to its higher molecular weight and linear structure whereas 2,3,5-trimethylhexane is not linear.

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Most popular questions from this chapter

(a) Draw the two chair conformations of cis-1,3-dimethylcyclohexane, and label all the positions as axial or equatorial.

(b) Label the higher-energy conformation and the lower-energy conformation.

(c) The energy difference in these two conformations has been measured to be about23 k´³â€‰(5.4 k³¦²¹±ô)per mole. How much of this energy difference is due to the torsional energy of gauche relationships?

(d) How much energy is due to the additional steric strain of the1,3-diaxial interaction?

(a) Draw and name the five cycloalkane structures of formulaC5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.

(b) Draw and name the eight cycloalkane structures of formulaC6H12that do not show geometric isomerism.

(c) Draw and name the four cycloalkanes of formulaC6H12that do have cis-trans isomerism.

Question: Using the general formula for alkanes

(a) Predict the molecular formula of theC27straight chain alkane.

(b) Predict the molecular formula of the alkanes containing 42 carbon atom with extensive branching.

Draw the structure that corresponds with each name.

(a)3-ethyloctane

(b)4-isopropyldecane

(c)sec-butylcycloheptane

(d)2,3-dimethyl-4-propylnonane

(e)2,2,4,4-tetramethylhexane

(f)trans-1,3-diethylcyclopentane

(g)cis-1-ethyl-4-methylcyclohexane

(h)isobutylcyclopentane

(i)tert-butylcyclohexane

(j)pentylcyclohexane

(k)cyclobutylcyclohexane

(l)cis-1-bromo-3-chlorocyclohexane

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentanealong theC2−C3.PlaceC2in front, represented by three bonds coming together in a Y shape, andC3in back, represented by a circle with three bonds pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and ethyl group on the back carbon. Begin your graph at 00thedihedral angle and begin to turn the front carbon. Show the Newman projection and the approximate energy at each600of rotation. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).

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