Organic Chemistry

(Dana P.) #1
Problems 727


  1. When a compound with molecular formula undergoes acid-catalyzed hydrolysis, one of the products that is isolated
    gives the following NMR spectrum. Identify the compound.

  2. List the following compounds in order of decreasing frequency of the carbon–oxygen double-bond stretch:

  3. a. If the equilibrium constant for the reaction of acetic acid and ethanol to form ethyl acetate is 4.02, what will be the
    concentration of ethyl acetate at equilibrium if the reaction is carried out with equal amounts of acetic acid and ethanol?
    b. What will be the concentration of ethyl acetate at equilibrium if the reaction is carried out with 10 times more ethanol than
    acetic acid? Hint:Recall the quadratic equation: For


c. What will be the concentration of ethyl acetate at equilibrium if the reaction is carried out with 100 times more ethanol than
acetic acid?


  1. The NMR spectra for two esters with molecular formula are shown below. If each of the esters is added to an aqueous
    solution with a pH of 10, which of the esters will be hydrolyzed more completely when the hydrolysis reactions have reached
    equilibrium?


10 9 8765 4 3 2 1 0
δ (ppm)
frequency

10 9 8765 4 3 2 1 0
δ (ppm)
frequency

(^1) H C 8 H 8 O 2
x=



  • b; 1 b^2 - 4 ac 21 >^2
    2 a


ax^2 +bx+c=0,

CH 3 COCH 3

O

CH 3 CCl

O

CH 3 CH

O

CH 3 CNH 2

O

10 9 8765 4 3 210
δ (ppm)
frequency

(^1) H
C 11 H 14 O 2

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