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The following data for isomeric four-carbon alcohols show that there is a decrease in boiling point with increasing substitution of the OH-bearing carbon. How might you account for this trend?

1-Butanol, bp 117.5oC

2-Butanol, bp 99.5oC

2-Methyl-2-propanol, bp 82.2oC

Short Answer

Expert verified

The higher the branching of the OH-bearing carbon of the alcohol compound, the lower will be the boiling point.

Step by step solution

01

Boiling point of alcohol

Alcohols and Phenols have greater boiling points due to hydrogen bonding.There is an attraction of +ve polarized –OH hydrogen and -ve polarized oxygen, and they both hold the molecule closer together, which increases the boiling point.

02

The trend for the boiling point

Generally, a series of isomers with branching has a low boiling point. The more nearly a compound becomes spherical, the more the surface area will become less than a straight chain compound with the same molecular weight and functional group present. The smaller the surface area of the compound, the fewer will be the van der Waals interactions (weak forces), which causes the covalent molecules to get attracted to one another.

Moreover, branching in alcohol compounds makes it more difficult for OH groups to approach each other and form hydrogen bonds. Thus, 2-methyl-2-propanol contains fewer hydrogen bonds than 1-Butanol having the same volume, and less energy is required to break them in boiling.

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Most popular questions from this chapter

Question: How would you prepare the following compounds from

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More than one step may be required.

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