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Chapter 20: Q8P b. (page 1053)

Question:

  1. Determine the structure of the carboxylic acid whose proton NMR spectrum appears below.
  2. Draw the NMR spectrum you would expect from the corresponding aldehyde whose oxidation gives this carboxylic acid.
  3. Point out two distinctive differences in the spectra of the aldehyde and the acid.

Short Answer

Expert verified

Answer

(b). The NMR spectrum is given below.

Step by step solution

01

NMR spectrum

NMR spectrum gives information about the chemical environment of the organic molecules. Two types of NMR one is proton NMR, and the other is carbon-13 NMR.By identifying the singlets, doublets, or multiplets, we can determine the molecule's structure.

02

Structure of carboxylic acid

(b) The multiplet between chemical shifts 2 and 3 is drawn as pentet; the splitting is equally by an aldehyde proton and group. The coupling constants were unequal, by which the actual splitting pattern will be a complex multiplet.

The NMR spectrum of aldehyde

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Most popular questions from this chapter

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.

Use chemical equations to show how the following accidents cause injury to the clothing involved (not to mention the skin under the clothing!)

  1. An industrial chemist spills aqueous H2SO4on her nylon stockings but fails to wash it off immediately.
  2. An organic laboratory student spills aqueous NaOHon his polyester slacks.

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a)methyl salicylate

(b) methyl formate (32°C)

(c) ethyl phenylacetate

Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a) propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid

The IR, NMR, and mass spectra are provided for an organic compound.

  1. Consider each spectrum individually, and tell what characteristics of the molecule are apparent from that spectrum.
  2. Propose a structure for the compound, and show how your structure fits the spectral data.
  3. Explain why an important signal is missing from the proton NMR spectrum.
See all solutions

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