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Rank the given solvents in decreasing order of their ability to dissolve each compound

(a) HCOO-Na+

(b)

(c)


Solvents

Ethyl ether, water, ethanol, dichloromethane

Short Answer

Expert verified

(1) Decreasing order of solvents’ ability to dissolve sodium acetate:

Water >ethanol > ethyl ether>dichloromethane

(2) Decreasing order of solvents’ ability to dissolve 2-methylnapthalene:

Dichloromethane >ethyl ether >ethanol >water

(3) Decreasing order of solvents’ ability to dissolve 1-napthol:Dichloromethane>ethyl ether>ethanol>water

Step by step solution

01

Solubility of sodium acetate

The general principle followed to determine solubility is,“like dissolves like.”

Compounds which have similar polarity tend to get dissolve in each other. Thus,

sodium acetate which is ionic and most polar out of the three solutes given, will dissolve

in water which is most polar out of the given solvents. Sodium acetate will dissolve

slightly in ethanol and will be insoluble in ethyl ether and dichloromethane

02

Solubility of 2-methylnaphthalene and 1-naphthol

2-methylnapthalene and 1-napthol are non-polar; and out of the given solvents,

ethyl ether and dichloromethane are non-polar. Thus, 2-methylnapthalene and 1-napthol will be insoluble in water, partially soluble in ethanol, and soluble in diethyl ether

and dichloromethane

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Most popular questions from this chapter

Show how the following ethers might be synthesized using (1) alkoxymercuration-demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

  1. 2-methoxybutane
  2. Ethyl cyclohexyl ether
  3. 1-methoxy-2-methylcyclopentane
  4. 1-methoxy-1-methylcyclopentane
  5. 1-isopropoxy-1-methylcyclopentane
  6. Tert-butyl phenyl ether

Which of the following ethers can be formed in good yield by condensation of the corresponding alcohols? For those that cannot be formed by condensation, suggest an alternative method that will work.

(a) dibutyl  ether

(b) ethyl  n-propyl  ether

(c) di-sec-butyl  ether

(a) When ethylene oxide is treated with anhydrous HBr gas, the major product is 1,2-dibromoethane. When ethylene oxide is treated with concentrated aqueous HBr, the major product is ethylene glycol. Use mechanisms to explain these results.

(b) Under base-catalyzed conditions, several molecules of propylene oxide can react to give short polymers. Propose a mechanism for the base-catalyzed formation of the following trimer.

Question. (A true story.) An inexperienced graduate student moved into a laboratory and began work. He needed some diethyl ether for a reaction, so he opened an old, rusty 1-gallon can marked “ethyl ether” and found there was half a gallon left. To purify the ether, the student set up a distillation apparatus, started a careful distillation, and went to the stockroom for the other reagents he needed. While he was at the stockroom, the student heard a muffled “boom”. He quickly returned to his lab to find a worker from another laboratory putting out a fire. Most of the distillation apparatus was embedded in the ceiling.

(a) Explain what probably happened.

(b) Explain how this near disaster might have been prevented.

Question. Grignard reactions are often limited by steric hindrance. While Grignard reagents react in high yield with ethylene oxide and monosubstituted epoxides, yields are often lower with disubstituted epoxides. Tri- and tetrasubstituted epoxides react with difficulty, if at all.

(a) Show how to make these alcohols by a Grignard reacting with an epoxide.

(b) These alcohols cannot be made by a Grignard plus an epoxide. Show the reagents that would be required and why that reaction would be unlikely to succeed.

See all solutions

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