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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 掳C ethanol, bp 78 掳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

TheC=Odouble bond has a dipole moment of about 2.4Dand a bond length of about 1.23 鈩�.

  1. Calculate the amount of charge separation in this bond.
  2. Use this information to evaluate the relative importance of the following two resonance contributors:

(R is a general symbol for a carbon-containing group)

N-Methylpyrrolidine has a boiling point of81慰C, and piperidine has a boiling point of106慰C.

  1. Explain the large difference (25慰C) in boiling point for these two isomers.
  2. Tetrahydropyran has a boiling point of 88慰C, and cyclopentanol has a boiling point of 141慰C. These two isomers have a boiling point difference of 53慰C.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 150慰C, and N-methylacetamide has a boiling point of 206慰C, for a difference of 56慰C.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).

Rank the following species in order of increasing basicity. Explain your reasons for ordering them as you do.

Rank the following acids in decreasing order of their acid strength. In each case, explain why the previous compound should be a stronger acid than the one that follows it.

Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with strong nucleophile sodium ethoxide, Na+ - OCH2CH3.

(a)

(b)

NH+4

(c)

CH3CH2Br

(d)

BH3

(e)

CH3COOH

(f)
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