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Chapter 9: Q10P (page 402)

Indicate whether each of the following solvents is protic or aprotic:

Short Answer

Expert verified
  1. Chloroform is an aprotic solvent.
  2. Diethyl ether is an aprotic solvent.
  3. Acetic acid is a protic solvent.
  4. Hexane is an aprotic solvent.

Step by step solution

01

Definition of polar protic and polar aprotic solvent

Polar aprotic solvent: The polar solvent molecules do not have a hydrogen bonded to an oxygen or to a nitrogen鈥攖he direct relationship between basicity and nucleophilicity is maintained.

protic polar solvent鈥擳he polar solvent molecules have a hydrogen bonded to an oxygen or to a nitrogen鈥攖he relationship between basicity and nucleophilicity becomes inverted.

02

Explanation

  1. Chloroform (CHCl3) doesn鈥檛 have any O or N atom to form H bonding with its lone pair. So, it is an aprotic solvent.
  2. Diethyl ether (CH3CH2OCH2CH3) has H linked with O to form H bonding So, it is aprotic solvent.
  3. CH3COOH has H atom linked to an O atom. So, it is protic solvent.

d. Hexane doesn鈥檛 have any O or N atoms and also doesn鈥檛 have any H attached to them.So, it is an aprotic solvent.

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Most popular questions from this chapter

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

c. How would the products differ if the starting material were the trans isomer? Are these products optically active?

d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly?

e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?

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Methoxychlor is an insecticide that was intended to take DDT鈥檚 place because it is not as soluble in fatty tissues and is more readily biodegradable. It, too, can accumulate in the environment, however, so its use was also banned鈥攊n 2002 in the European Union and in 2003 in the United States. Why is methoxychlor less soluble in fatty tissues than DDT?

Draw the configuration(s) of the substitution product(s) formed from the reaction of the following compounds with the indicated nucleophiles:

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