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Chapter 2: Q33 P (page 138)

Dimethyl ether and ethanol are isomers. Their boiling points are very different, however. Explain why these two compounds have dramatically different boiling points.

CH3-O-CH3 CH3CH2-OH

dimethyl ether, bp -24 °C ethanol, bp 78 °C

Short Answer

Expert verified

Ethanol have hydrogen bonding while dimethyl ether shows weaker intermolecular forces of attraction.

Step by step solution

01

Step 1:

Dimethyl ether have weaker intermolecular forces (weak dipole-dipole interactions) which required less energy to overcome the bond when compared to ethanol. And there are no hydrogen atoms directly attached to oxygen to form hydrogen bonds.

02

Step 2:

Ethanol have stronger Hydrogen bonding (it can accept one H-bond, and can donate one H-bond) which require more energy to overcome this bonding, which leading to a higher boiling point than dimethyl ether.

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Most popular questions from this chapter

Predict which member of each pair is more soluble in water. Explain your prediction.

(a)

(b)

(c)

(d)

(e)

(f)

The following acids are listed in increasing order of acidity. In each case, the acidic proton is shown in red.

(a) Show the structure of the conjugate base of each acid, including any resonance forms.

(b) Explain why X is a stronger acid than W.

(c) Explain why Y is a stronger acid than X.

(d) Explain why Z is a stronger acid than Y.

For each of the following compounds,

  1. Draw the Lewis structure.
  2. Show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.
  3. Estimate whether the compound will have a large, small, or zero dipole moment.

(a) CH3-CH=N-CH3

(b) CH3-CH2OH

(c) CBr4

(d)

Structure (d)

(e)

Structure (e)

(f)

Structure (f)

(g)

Structure (g)

(h)

Structure (h)

N-Methylpyrrolidine has a boiling point of81οC, and piperidine has a boiling point of106οC.

  1. Explain the large difference (25οC) in boiling point for these two isomers.
  2. Tetrahydropyran has a boiling point of 88οC, and cyclopentanol has a boiling point of 141οC. These two isomers have a boiling point difference of 53οC.Explain why the two oxygen-containing isomers have a much larger boiling point difference than two amine isomers.
  3. N,N-Dimethylformamide has a boiling point of 150οC, and N-methylacetamide has a boiling point of 206οC, for a difference of 56οC.Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers. Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).

Calculate the pH of the following solutions:

(a) 5.00 g of HBr in 100mL of aqueous solution

(b) 1.50 g of NaOH in 50mL of aqueous solution
See all solutions

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