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Chapter 20: Q6P b. (page 1049)

Question: Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(b). Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Short Answer

Expert verified

Answer

(b) Pentan-1-ol cannot be removed from pentanal by acid-base extraction. Instead, it can be removed by the distillation method.

Distillation of pentan-1-ol and pentanal

Step by step solution

01

Distillation

Distillation is one of the separation methods used for separating liquids by converting liquid into vapors, and then again, it is condensed into a liquid form. It involves different boiling points of liquids.

02

Removal of impurity

(b) Pentan-1-ol cannot be removed from pentanal in acid-base extraction. So, these two can be separated by the process of distillation. The boiling point for pentan-1-ol is higher than pentanal because of hydrogen bonding.

Distillation of pentan-1-ol and pentanal

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Most popular questions from this chapter

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Show how Gabriel synthesis are used to prepare the following amines.

  1. benzylamine (b) hexane-1-amine (c) 蠏-amino butyric acid

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Ethyl p-nitrobenzoate has been found to undergo saponification faster than ethyl p-methoxybenzoate.

(a) Consider the mechanism of saponification, and explain the reasons for this rate enhancement.

(b) Would you expect ethyl p-methoxybenzoate to undergo saponification faster or slower than ethyl benzoate?
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